Vanilla to Owner

I was flying out in the late afternoon for working again but she had got my son to cover her daycare granddaughter duties for a bit. As she put it " you have some priority items to take with you "

We ran up the road to Joslyn's shop. Before we went in she told me I had to do the shopping and picking out, she was only going to observe.

" You're going to find and pick out another dildo the length and diameter are your choice but the diameter must be a minimum of 1/4" larger and little man is 1" diameter, I won't you to look at a butt plug if you find one you like. The other requirement is additional lube like you sampled but larger size, but you need to discuss you needs and see if she has other suggestions".

I said some more of the 2 I had tried would adequate. She remarked " I said you need to discuss other options she thinks might be competitive or possibly better yet , are you clearly understanding me,?" Yes man., I do. With that we headed into store. Again I was happy we appeared to be the only customers. Joslyn was not alone she was talking to another clerk. Apparently she was newer at this based on her comments.

 

Joslyn welcomed us back and asked how could she help us. My wife thanked her and said " he wanted to come back for some additional things , after this weekend " . Joslyn with a smile turned to me " well what can we help you with today? I take it you enjoyed your other selection, how did you like those different lubricants"?

They both worked better than my old lube but was wondering if you others you would suggest? "Well those were two very popular anal lubes and are responsibly priced I have some others that run a bit higher but many feel they are superior, I don't have sample sizes but I stock smaller size containers ".

I need to get a small bottle of each of the others today regardless. I have 2oz and 4oz in stock and also larger 12oz but 4 oz is my biggest mover and lasts quite a while for most". Let's go with 2oz , but I will try a small bottle or your other suggestions also.

"No problem, honey, what else are you interested in?" Well, I need to see about a somewhat larger dildo. " Are you looking at longer or bigger diameter, or both ". I uh, guess a little more diameter and
maybe a little longer by an inch or two.

"Well that gives us some good options, would you mind if Donna joins us she just started here but has a lot of prior experience ". I guess that's OK, my wife spoke " the more the merrier, he's still kinda avirgin on this". They both smiled at the comment.

Donna took the lead, " so you have the "little boy " that's an excellent choice for a beginner, but you're wanting more diameter and some more length ". Yes mam, maybe a eighth or quarter inch diameter. "Well most are quarter inch steps, let's take a look, but mostly the will start having phallic shapes unlike the , straight shaft of the "little boy " is that alright?. I guess, had not really thought about it.

"It's just at the tips will have the penis head shape mostly, some have vien texture on shaft or still smooth, some guys like the extra texture increases sensation ". I guess it's optional but probably smooth if you have it.

She selected several and sat them up on counter for my closer inspection. I hesitated picking any of them up. Donna handed me the last one as it came out. " This is a very popular favorite it's a quarter inch bigger and two inches longer same material and feel it has a slightly more rigid flex, go ahead bend it around and feel it" I worked my hands to see how firm it was. "It has a nice feel but firm enough you can guide it, the curve allows you to work your P-spot easily ". You mean prostate? " well Yes but its really more than that it's like you're wife's G-spot or the males version ". I have a nexus prostate stimulator but have moved to these also.

Well check the others out, compare the texture. material and firmness see what feels right in your mind, everyone is different, they all work by hand or harness as desired ". I checked the other 3 the matador as she called it seemed close to the little man. I turned to my wife and asked her thoughts, I probably should not have.

" Sweetie its your shopping trip and it's your little twat, pick what you want to use on yourself, they all will fit my harness when needed ". Donna's response " do you want to compare it to the plus matador it's an extra 1/8 more in girth and 1 inch longer ".

I don't know about a bigger diameter it might be too big. " let's put them side by side to compare, as you see it's not much bigger and it's very popular, I would think you could accommodate it without any problem as long as you're patient and don't rush the penetration the anus has range".

I held them up and looked it was only a small change . I will try the Matador Plus, I guess it's a better choice. "Wonderful I feel certain your going to love it's performance , is there anything else besides your lubricants?"

Well, I kind of wanted to check out a butt plug maybe. " Wonderful let's move over we have some great choices are you wanting to look at larger ones or similar to your dildo ?" I guess the similar diameter to the plus. " Would you like a suggestion " sure I guess " I would recommend going with a 2" diameter plug it would prepare your sphincter and its still smaller than most can accommodate easily ".

My wife spoke up " Indeed that sounds like a good suggestion, I was wondering about larger ". " I would start with 2" it will make a perfect choice to start training his anus ".

I said let's look at two inch any other suggestions ? Well I suggest we look at ones with longer neck between plug and base plate also tapered plate for wearing comfort in case you decide to go longer times with it inserted "

I don't know " trust me you probably will find occasionally you may keep it inserted possibly all day". I looked at my wife and she nodded at me. OK sounds like good recommendations. Well what color you have violet and blue dildos do you want a plug that matches or a black, pink or red same material as you little man. I will go with blue.

"Great can directly match you're plus in that case, matching sets are extra nice, anything else you desire today?. No I think this is more than enough.

We went over to checkout. Roslyn and Donna both thanked me for my business and said feel free to return and they are more than happy to support us as I explore new things. My thanked them for aiding me in my selections and to always point me in right directions.

After we left she told me I needed to pack my new treasures in my suitcase so they are available if needed. She reminded me the toys are only used on her directives not for my use otherwise.

I knew then I would be exercising during this trip even more.

 

Well made my flights and arrived when I landed texted wife was going to eat and hit hotel. She told me to go shopping for more non-life condoms and to get 2 of bigger package for home and travel since the last 2 were in my zippered pouch will dildos if I wanted also low on protective pads maybe a small package for this week and next week traveling.

I hit a Walmart on my way got everything and went to eat and hotel. She called and asked what time would I arrived at hotel. Figured about 7pm. She said verify arrival and she would text instructions.

I figured I was not getting to skip for my travel day. I got to hotel texted and moments later her text popped up.

Shave body. shower, cage and bra only dress and get bed and Polly prepared, have nexus. new plug and dildos pad and new lubricant , washcloth available and text Ready for Exercise

Doing that it was not a suprising she was going to have me test the new toys. I setup phone for her viewing and she video called.

" Let's start with the new plug but then the Matador plus you can leave others stored, tonight your trying all new things ".

She had me roll a condom on both for easy cleaning up afterwards. I then took the blue plug and began massaging the tip as she directed. The tapered tip starts smaller than the nexus but the top is 2 inches which is over double of the nexus and almost double of the little man dildo following a 60% increase to the matador plus.

She had me work and massaging my twat before beginning penetration. The tip easily eased through my sphincter. She then had me continue to insert additional depth she had a reasonable view of the proceedings and how much was inside. At about half in she had me start slowly in and out movement. It was not reaching my prostate and felt a little different from little man due to my twat being enlarged and reduced with the tapered plug.

After a few minutes she had insert it deeper I could feel increasingly more stretch but still comfortable. The new lubricant seemed to glide with less tug on my sphincter. She then had me slowly increase the penetration I began to feel some discomfort and a little burning sensation. I spoke up she had me hold everything still until it calmed down. Then slowly pressing more into me again we paused. She congratulated me for my progress and effort. She asked "do you realize how much you're little twat has taken in?"

No, not really while holding it in place she had me take a finger and feel how little was left outside as I slid my finger up I estimated less than a half inch was left to the peak means my sphincter had 1.75 diameter worth of plug inside.

" OK Sweetie I think you're ready to accept the rest inside your bottom, go ahead relax and slowly finish taking it, you can do it" I gentle added pressure and with a slight return of burning sensation it suddenly sucked inside things quickly calmed down.

" Wow it just jumped in, it looked like it pulled away from your fingers. It basically did it jumped in. Well the base plate looks very cute tucked into your cheeks " I don't know can't see it but I feel it.

" Is it comfortable, move and get up walk around see and tell me how it feels " I moved off the bed to stand. Other than the base plate touching my cheeks slightly everything was fine. I felt the fullness which was a bit different, I was oozing fluid but no spurt I described everything to her.

"Get you protective pad under Pollys slip let's have you do a little humping her. See how it feels with you twat filled up". I proceeded to hump Polly she then asked for report on my wet spot size. It was significant almost 5 inches both ways. I knew it was at times putting pressure on my prostate from how it felt.

"Was that comfortable? Looks like you're pinkie was happy you made a serious deposit size ". It felt nice at times it rubbed my prostate.

"Well let's remove it so you can take a short session with the Matador plus. You're going to have to go slow and gentle the taper on is steeper on the coming out ".
I had not thought of that it was a a quarter of the front taper. I positioned the pad to protect things. I worked to relax myself I applied a very slow steady pull against the base plate. I could feel my sphincter muscles but the lube was doing well. I paused a few times then suddenly out it popped once the big part passed it slipped right out. .

She congratulated me for a successful penetration and performance . "OK let's see how the Matador plus performs for you. I relubed my twat and the MP.

"OK, Sweetie let's get it into you and see how it feels. I guess my sphincter was stretched or relaxed it took almost no effort and in it slipped I basically bottomed it out and waited on her instructions. "Wow. you took the whole thing all at once, I guess you're completely comfortable with your little twat filled up, as you used to say is it a nice poke, well I don't hear you ".

It feels fine it just glided right inside me. I did not spurt anything but I am leaking.

" OK Sweetie let's have some exercise with slow, medium and fast stroking to compare the feelings versus the little man. Doing as she requested I was getting more sensations from this model I suppose from its having a shaped head a maybe it size difference. I found alternating stroke speed and distance created the most pleasant feeling.

" you've had enough fun let's wrap it up so you can clean everything up and get to bed for sleeping. We have plenty of time to experience all of this ".

 

Indeed the journey continues.

 

I setup my next trip to work through weekend into second week. My wife was not pleased with that. He response was a question " you know the song 12 days of Christmas?" My answer of sure everyone does why?

"You Sweetie , will be singing and performing the 12 days of Penance and also performing the required tasks or suffer the consequences, since you chose be gone 2 weeks". I had not realized the weekend included Mother's Day as well.

My punishments or penance started Monday night and runs through till next Friday evening with me getting home a week from Saturday. This will be my 4th night and don't know what she will have me doing but so far everything has not been real fun. More how humiliating and frustrating she can toy with me over our video calls.

I have already gotten demerits for be late to post my journal. I have been working split shifts with long hours only to return to hotel to clean up in time for her playtime with me. Her threat of a severe response to fail any tasks looms in my head all day.

 

I am trying. It has been a grind. I am fixing to go in to work with maintenance group today. I plan to be down tomorrow for work beyond computer. But as she put it last night. Saturday evening and Sunday she has priority and I will be at her command.

I anticipate a busy schedule. Hope your new piercing recovery continues well.

 

My twelve days of penance:

ON THE 1ST DAY:
Monday night my video directed penance
Play and masturbate for 15 minutes per her directions while receiving a series of injected remarks about my tiny pinke not being able to get even an semi hard condition despite all the efforts and attention. My tiny thing not doing anything but being a leaky little faucet. It is so limp and useless other than to keep it out of sight its really a waste of a good cage meant to prevent a real working penis from getting hard and erect. Another wasted opportunity to cum and squirt something out. Finally the time was up, I cleaned up my dribbled juices and put my oversized micro cage back on.

ON THE 2ND DAY:
Tuesday night my video directions:

I was to lubricate and penetrate myself with my nexus prostate massage tool and follow her instructions for its use over the next hour. It included the use of the new lubricant and the injector to pre-lube inside myself for better lasting lubrication. It was a sample added to my purchase of last dildo and anal plug with a note telling it would make my new toys work my little twat much better and they come in packages of 3 if I need more for my future. I had to fill it and insert it so the wife could watch. I also had to describe how it improved the use of my toys.. It really did a better job getting a good load of lubricate inside my bottom and made for improved smooth stroking motion. The muscles wipes a lot of as it passed by and using fingers to work extra lube is much more trouble. My wife told me on my return I would be going back to purchase some packages of them for certain, and I would be thanking them for their suggestions and help. I proceeded to pump and penetrate myself and I was enjoying the sensations of the prostate stimulation. I was not able to make anything happen despite my trying beyond putting out serious amounts of precum. I again was reminded that my little pinke just leaked and laid limp during it all.


ON THE THIRD DAY:

Wednesday night directions:

Again use my injector to fill my twat with lubricant before using my Mat Plus dildo on my twat. She limited this session to 45 minutes filled with colorful comments about how easily it penetrated and pumped into my puckered little twat and it easily filled me. I again got reminded about my limp pinke and nothing seemed to even try to get it to rise up even a little. Finally she called time and said it was very disappointing that the new bigger dildo was not getting me excited enough she really thought that a larger and longer cock was going to help my excitement levels more. I got done cleaned and sanitized all the equipment and called it a night.

ON THE FOURTH DAY:

Thursday night directions:

I was to inject my lubricant and use my butt plug. I was to put it in and leave it for 4 hours while worked on paperwork and my trip reports. She checked me every little bit by video calls so I could show her my twat with the blue outer plug nestled between my cheeks. She sometimes would have me stop work and do some rotating and even pull it out play with my expanded hole before plunging it back in. She toyed with the thought of me wearing it to bed for the night. Finally she directed me to remove it and perform clean up and to shower again before bed.

ON THE FITTH DAY;

Friday night directions:

She had me lube up and use my first dildo to entertain my little twat. This time was another hour session. I followed her instructions for speed, and length of penetrations, angle of attack as she had me rotate its curve to attack my prostate on and off. Finally she wrapped it up with clean up and shower for bed.

ON THE SIXTH DAY:

Saturday I worked with maintenance crews during a cold shut down but we started early so I was done earlier than the split shifts I had been doing. I just finished up with almost 2 hours for her pleasure. I started with my cage off and humping Polly then moving on to having a double round of lube injected before using both dildos on myself through a full series of various attacks. She then had me plug myself after that I sit here filled with my blue butt plug updating my journal as directed with all the entries to date. She has been upset my my lack of keeping my journal current. She is checking periodically and informed me to do a good job with my notes. She said to text her when I am caught up and she would review. If I do well she may let me remove my plug for bed tonight if not I will wear a pad in back of my panties and sleep with it. I am wrapping this up and going to text her and will await her response on status. She told me Sunday I will be hearing from her early and I would have things to do during the day and evening since I won't be going into the plant to work till Monday now. Sunday is Mothers Day and I have chosen to not be at home with her, instead I decided to work and stay over. That is why the 12 days from her got me my 12 days of penance.

Good evening and everyone wish me luck. I could use some.

 

Thanks already expecting a busy day and evening at her back and call long distance.

 

ON THE SEVENTH DAY:

Sunday started with her call asking how I had enjoyed my night with my twat filled and plugged. I told I had awakened several times and was difficult going back to sleep as my mind was busy thinking about being filled with my plug. She asked about leaking both front and back. I had some lubricant work out and of course my pad in front had a fair amount of precum. She was pleased that I had enjoyed my overnight penetration as she referred to it.

Well I have some shopping for you to complete this morning gep your pen and paper out. You need some more mattress protection pads get 24x36, better pick up more of your panty liners both sizes., get 2 twin packs of fleet saline enemas or four individual from the drug area, another of the regular water base lubricant, another package of condoms non lubricant if you need more shaving supplies for body. We want you clean and no stubble on you dermatologist trip after you get back. Get yourself feed because you're only going to get a supper break to go back out.

Text me on returning and I will tell you the next steps. I had already figured out I was going to be douching my rear end.

Her final comment " make sure you keep your twat filled with you pretty blue plug while you shop. "

I was off after that.

 

Sunday continued:

I returned with all my shopping and ate decided to bring my other meal for later back as well. Let her know I had returned and was awaiting her contact to continue.

She sent a text with list and her video call time slot.

Give yourself an enema use two bottles to assure a good flushing out of my twat and to use the standard water base lubricant with enema process.

Shave full body and shower.

Remove my cage and full clean it. Leave it off but no playing with your tiny pinke.

Verify text completion prior to appointment time.

I got it all done about 10 minutes early and texted.

With the call she did a shave quality inspection and I passed. She then told me to prepare my lubricant injection with my new lube and fill myself with 2 rounds.

She had me place a protective pad and get on all fours to start. Round 1 was my nexus prostate toy she had me set camera up so she could monitor my pinke and its limpness and leakage. Her mention of limpness being highlighted.

Next I was to lube my rosebud and the toy . Then " OK Sweetie slowly penetrate your twat with that hard shaft until it bottoms out." I worked it around and relaxed as I opened up and it slipped slowly in. She then started laughing " oh it's so cute when you're limp pinke sports that little dollop of spunk out, like a tiny pop gun of course only one bullet ". "Alright start your kegel muscle contractions until I tell you to stop". After 15 minutes of exercise I had dripped a nice small puddle as I dripped a each few cycles. "Alright let's have you get on your side , move so your next puddle will be separated. ". I scooted down and played on my side so she still could watch my emissions.

" alright Sweetie let's get you stroking that hart shaft and see if you're tiny pinke will get at least somewhat excited the first round certainly failed ". "There was a time you're pinke would get hard like you're nexus shaft of course not as long , it's 4 1/2" inches and you maybe reached a little over 3 on a great night, of course neither of us has seen that in a long time, but we don't need that anymore do we ".

" It might surprise us who knows maybe you're going to find a way for your twat to get some kind of a rise going, at least maybe a semi hard, wouldn't you enjoy seeing it inflate at least a little bit?". I can't even remember what my erection looked like hardly.

"Well start pumping that hard little shaft in and out let's see what we can stir up". She began a series of angle and speed commands as she monitored what my leaking was doing and if my pinke reacted differently for any particular motion and angles. She narrowed the changes into only 3 variations. I had lost track of the time and had closed my eyes and only listened to her and the low noises of the nexus as it slurped in and and out. I was getting lost in the waves of enjoyable feelings. She then had me settle into a single motion at a medium speed.

After awhile she had me take my other hand to position and use my fingernails to circle my areola first the left then right. I felt like electricity was shocking me and I spasms occured in my groin. Not an orgasm but a crescendo of tiny spasms. Next my fingernails were directed to flick my nipples. It was delicious and intense almost painful. I asked to stop "No" so I continued.

She finally had me remove my finger's but the nexus was still pumping me. I calmed down but my nipples were on fire. I started to massage them and was immediately stopped. "Only what I tell you touch only what and how I tell you".
Finally she told me to stop and to withdraw the shaft. My dildos and plug were adjacent to me on another pad as she had me set up. I placed the nexus near them I noticed it wasn't soiled, I guess the fleet douching had cleaned things well.

Next was another injection of lubricant followed by a second. " We want to keep plenty of lubricant inside your little twat , now take your small dildo and prep it then slide it in to fill up you bum".

After that another similar round of pumping and angles. After some time it hot down to another single pattern. This time I had to do various pinch and pull attack's on my nipples. That created a different series of pain and pleasure but she ended that quickly. After some additional pumping timeout was called and the shaft was withdrawn from my bottom. I placed it with the nexus.

Next was the Matador plus the largest dildo. Another double lubricant injection squirted into my bowels. After that a brief get acquainted play to ease the head into my twat she had me pause then a little twisting of the shaft , followed by a command " plunge it into your little twat and fill yourself up with that wonderful shaft" With that I began a steady plunge into my rear it easily slipped right into my crack.

"Well you took that nice and quick was it comfortable for you?" Yes I've got tons of lubricant in there it just glided right in. " well I think you're douches helped as well, we will start having you douche you're twat before your play sessions , your toys stay cleaner as well ".

She again had me pumping myself through various patterns before finding her choice. I again began to zone into the feelings generating in my backside as I stroked the shaft into myself. Lost in her voice and more slurping sounds. I felt some of the slimy lubricant as some was coming out of me. My sphincter was getting more relaxed. It felt different almost loose a I plunged in and out.

I felt juices on my leg at times if I didn't tilt my body enough. My short stub didn't clear things. She made a few comments about not enough there to get away from leg drips. I finally was told to very slowly slid the shaft all the way out.

"OK Sweetie let's plug you're twat so all that lubricant isn't dribbling out, let's see how loose your hole is , see how quickly you can accept that plug ". I took the plug and put some pressure on it as I worked it in a small circular motion. My sphincter was apparently very relaxed and I suppose stretched some the tip slid in as I began to add some pressure and it suddenly popped in and sucked right to the base. I got no burning sensation at all. I acknowledged I had gotten it all in.

She proclaimed her delight " that's fantastic, any problem or pain ?"
No dear, it went in smoothly it was easy this time. " Well that little twat apparently likes being stretched and exercised , or it's just ready for bigger thing's ".

"Let's get yo a shower and your toys sanitized you will keep yourself plugged, put pads in your panties and your red bra on. That's enough clothes. Leave your pinke uncaged for now, no touch or play. " You have permission to do some paperwork for a bit I have some things to do. I will be in touch., remember no fondling of anything. "

 

As I continued my Sunday in my hotel room with my blue plug in my bottom, red panties with pads front and back for leaking with my red bra. I worked at my computer catching up on customer reports. When I got and sat down to pee I also needed to change both pads. Although still limp and almost fully turtled inside my pinke was still leaking. I had also oozed lubricant out . I cleaned up everything and and put in fresh pads.

She texted me and told me to go ahead with early dinner so next session would not be interrupted. I texted back I had brought takeout back to cover my other meal. She congratulated me for thinking ahead and happy for no needed gap in her plans. She said have myself wrapped up on reports by 4 pm and we would restart my activities into the evening.


As requested I wrapped up and shut down and waited for her call. I changed my pads again as well. The video call rang in.

" Are you ready to play some more Sweetie let's get your pretty plug out of your sweet twat and fill you with your violet shaft. But get your Matador also without a condom for now, let's get some more lube injected first ". I then filled and pushed the syringe in and pushed the plunger for 2 more loads. Then rolled fresh condom onto the violet shaft then lubed it.

She had me take a side position again so she view was my front again. " OK let's slide your pretty toy into your little twat where you like it". This time she only had me alternate 2 pattern's. I was easily slipping into enjoying the feelings. I began to reach and give my chest some attention. She quickly chastised me for trying to act without permission or direction. " if you want to play with yourself, ask for permission and describe what you're wanting to do, never help yourself ".

I was just going to massage, she cut me off. " I said you ask permission and describe how you want to play with yourself , not a lame comment, now keep pumping your twat and if you want to request something do it correctly ".

I had a desire to feel the extra intensity I had gotten earlier when she had me work on them before. It supercharged the feelings as I stroked against my prostate.

May I please use my other hand to play with breasts and nipples again like this morning? "You mean you want to pinch your nipples?" Well I was just going to circle and flick the a little. " No, I think not,". I was disappointed, she had me change methods to her primary choice from the morning.

My mind was focused in the feeling in my rear but also I longed to enhance the pleasure waves. I finally blurted out. May I please have permission to pinch my nipples with my free hand, please honey. She did not respond, please may I. " Are you begging to pinch your nipples Sweetie?"

Yes, please it really increases my feelings. "Well, let's do something else while I consider your request to play with yourself ". What else do you want, tell me. " get your Matador put it in your crotch and let your thighs keep it in place". I quickly got it and positioned it right under my sac and my thighs held it. I looked down at the blue shaft firmly sticking out like a real hard on. Something that my crotch has not seen in a long time. It was longer than I ever been even in younger years.

" Oh my Sweetie, to bad your pinke never got it up like that, I mean you used to get hard but never long and hard like that, it's nearly double what you once were." It was true I often dreamed of having a real chunk of meat yet this was small compared to other real dicks.

"Keep pumping and quit starring at your blue shaft your getting a gleam in your eyes". I continued to work my twat with my smaller shaft. I was wanted to ask again for permission to play with my nipples. She was quiet she doesn't allow me to view her on most calls. I kept waiting and hoping she would remember my request.

I finally broke down , honey my I please have permission pinch my nipples some? " I don't think you have earned that privilege, how bad do you want to pinch your your little nipples Sweetie?" I really want to pinch them it really helps my feelings .

"Well I suppose you could earn that privilege if you're so desperate to do it". Earn it what do you mean, what do I need to do to earn it, I am following all your directives.

"Well not much, I mean earlier you were very interested in your blue hard on sticking out at your crotch, I saw you starring at it". I was just thinking about my missing erections that's all. " Sweetie your erections never looked like that and I am not talking about the color ". I know honey its much more than I ever was. "Indeed I understand that probably better than you, the few times I indulged you urges for a BJ it didn't even reach the back of my mouth ". That was true she did not have any need to deep throat anything I offered.

" If you really want to pinch your nipples while you're pumping that violet shaft into your little twat, since you're begging too. All you need to do is a small task " I urgently wanted to edge into the zone I got to before. OK, whatever , what little task tell me, I will do it. "Really?, well I want your promise first ". I promised, whatever you want just tell me I will do it. " Alright but no backing out, full commitment " Yes name it so I can pinch my nipples.

"Alright, reach down and feel that hard blue shaft ".I moved my free hand onto the dildo. "STROKE IT, jerk off that meat" I began moving my hand. My precum had gotten on it my hand glided on the slick shaft. I really wanted to get this done and change to pinching myself. She spoke again " that's good ". Fantastic I was moving my hand up towards my chest.

"No Sweetie your not finished with the task , take that firm shaft and unclalmp your thighs hold it at its base". I removed it and held it . " OK let's see how it fits in your mouth now" I didn't know what to do, I froze. " Well what's your problem you promised to complete the task. Take it into your mouth otherwise your hand won't be free to play with your nipples that you were begging to pinch"

I was torn , I wanted to pinch them but she put a real price on it. " 10 seconds either your hand is by your side or pinching your nipples you begged for. 9 8,7,6,5,4 3,, I opened my mouth an in it went. I moved my hand to my left nipple. I tasted my precum on the shaft as it rested in my lips held by my teeth gripping it.

"See it's not that big a deal, I mean it's certainly bigger than your pinke but real man dicks come much larger". I nodded since speaking wasn't available. "That's right Sweetie can't have conversation with your mouth full of cock, how's your precum tasting? We've been working to freshen it up with your exercising ".

I was enjoying my chest and stroking my rear I was trying to overlook the dildo in my mouth. I focused on the one in my rear as it worked on the prostate.

I think you're nipples have seen enough action, let's have you finish cleaning off that hard shaft with your tongue. We need to roll a condom on it so we can swap it to your twat. I removed it and worked all the sides . " See there its easy like a long lollipop just a different flavor, you really did a nice job on that, looked like you may have enjoyed that a little , maybe ".

No I didn't I just wanted to get done with the task. " Listen you begged to play with yourself, you agreed to perform any task, it was totally your choice, you didn't have to do anything you begged ". I just wanted to enjoy the feelings I get, that's all.

"Look your doing penance for your decision to commit 2 weeks straight including the mother's day weekend. Your just lucky I have considered far worse things than sucking and licking on your favorite dildo flavored with your own precum.

I wasn't sucking on it, I just held in with my teeth. "Well Sweetie you always enjoyed me nibbling my teeth on your pinke guess you remembered that trick.," it was only too hold it without my hand. " Yes, you couldn't wait to pinch yourself on your nipples, quit whining you got what you wanted and begged for. It didn't hurt you to use your mouth and tongue on that firm shaft as you pinched your nipples and pumped your twat. Surprised me you didn't cum, maybe next time. "

"Roll that condom onto your favorite lollipop and swap it out, I think you still have enough lubricant inside your twat ". I did as directed and slid the shaft into me. I thought about it was just in my mouth and now I was pumping my twat with it. I felt odd about that my wife continued to direct my use.

As I was following her commands she remarked " I think you're actually getting a little bit of a semi hard on there Sweetie, you actually are coming out of your turtle shell ". I looked down, she was correct I was actually slightly starting to extend slightly. She had me change stroking to her choice for this dildo.

"My , that is the most action your pinke has shown in some time. What's going on. It didn't do that last time even with this stroke pattern. You put out the fastest leak but stayed limp. Are you getting a different feeling or something?.

No its about the same, I don't know. " What's your brain thinking as your pumping yourself? What's your daydreaming on?" I don't know nothing really. "Bullcrap, tell me what's in your brain thoughts". Well. I don't really know, a moment I thought about where the dildo had been as I penetrated my twat with it. I mean just a flash momentarily.

"Ah, so maybe that's part of it, you were thinking about having it in your mouth and them your twat. Guess maybe that's a little extra exciting "

No , it was just a quick flash. ",Well don't be to sure you're little pinke is almost to a semi hard on. Look at it, it's the most perked up in months. Even more than when I rode your to climax " The pinke is reacting as we discuss you sucking the cock in your twat "

I quit looking at myself I tried to get my mind somewhere else. I wanted my pinke to shrink back inside. " Bury that shaft and squeeze your cheeks, both your hand up and use your fingernails on your stiff nipples. I did as told, felt like dildo wanted too slid out. I felt electric and fire building as I tweaked myself.

I was almost getting spasms I was clinching. "Wow, look at pinke your approaching a true semi hard on. There's an inch and a half there I believe. This is amazing I bet if you're mouth was full of cock you might even get hard. Too bad we don't have a sanitized available. "

Despite not wanting to look I did my pinke was trying it's best to rise up. " Oh wait, I thought of something, your plug its sanitized stop tweaking your nipples and get it". I reached for it , I knew what was next. " Alright you know what to do " I reluctantly raised it towards my mouth and opened to take in the small tip and engaged my teeth.

" Alright you're mouth and lips are busy, get those fingernails back to your nipples. I again felt like electricity shocks. I closed my eyes trying to overlook my mouths guest. "Open your eyes and look at your pinke, it's not a hard on but that's the maximum life its had in a couple of years. Suck on that plug, take more in. Play with it. I about gagged as I did but I used my tongue I ended with it all inside and my teeth were holding the small connector and my lips brushed the end stop.

" oh that's a nearly perfect fit, work lips on the plug . I used my tounge to push and push back for a few minutes.

"OK. stop tweaking your nipples and let's ease that shaft out but keep your plug in place. I rearranged and pointed to the plug. "No. leave it in while you clean up yourself and toys. Then get a shower . After all that she allowed my plug to slip out if my mouth.

" You did very well , Sweetie. take a break and eat dinner. We will have another session later . I think you're plug needs to get up your twat now that you sucked it off. Put your pads and panties on for dinner.

I will call back enjoy yourself.

 

Well my jaws could tell I had spent considerable time opened to accommodate the dildo and plug. Similar to time at dentist. I relaxed and even caught a short nap. I remembered part of a dream from when my wife had rde me into a climax from rubbing me of against herself and her wonderful attack on my breasts and nipples. I had certainly leaked during this dream. I needed both front and back pads replaced. I figured I had put over 3 ounces of lubricant into my bowels. After cleaning and new pads felt fresh again. My using enemas had really made things less messy she was made note and several positive comments about its effectiveness.

I watched a little TV as I figured she'd be dialing in soon. I figured she had another marathon session waiting for my evening exercise as she put it. I had scrubbed and sanitized l the toys and lube injector up. I figured more lubricant was going to be on the agenda. She really took a liking on the neat and efficent means they put lube only up inside rather than all over. I appreciated it being much neater and way less messy. Cost effective they said on one use but decided with good cleaning and sanitizing I could reuse it safely a few times. Even the plunger rubber comes off and has no real crevices.

Heard my phone text chirp, it was her giving me a 15 minute warning. She also instructed me to remove the plug and fully clean and sanitize it as well. 2 protective pads ready along with washcloths and condoms.

She rang in for video link setup phone again. She told me to go look into front compartment of my large suitcase I had with me. I went over and unzipped it. She uses this section when we travel together I had not accessed it.

There was a new prostate toy with vibration and movement waterproof, our dildo harness and a air of stretchy rubber like panties with a dildo hole in front. I brought it all back to the bed.

"Well what do think Sweetie, since you have failed to complete your task to get yourself the handsfree dildo capacity, I have done your work " I have been shopping and researching "Hush, I don't want to listen to your whining. Go get a bath towel as extra protection. "

I came back. "Wrap it tightly around 2 pillows then adjust the strap on harness but put first protective pad over area. I wrangled everything around. " Now work the insert the Matador and then work the dildo panties onto it. With time and effort I got things arranged.

She had me add another towel and pad underneath this. "Alright no it's time to lube your honey pot up let's get 2 squirted in there." I already had filled the syringe and then reloaded. " Now roll a condom onto your favorite toy but don't lube it up yet ". Completing that, I waited.

"OK, now you're going to lube up that firm shaft ". I reached for my lubricant bottle. "No , not that " the other lubes in the bathroom, I had figured only needed the new brand.

" I've got a better idea, let's use natural lubricant " you want me to drop precum on it? She paused, " that's a really good idea, let's see how that might work, I was already oozing . "Take your panties off and let's see what you can provide " I pulled everything off and positioned myself and rolling the bundle on it's side for better target. I began to slowly squeeze and milk out a few drops . After a bit she spoke up, "Sweetie this isn't working out so good, let's move to plan B set the rig back upright so the wonderful hard shaft is vertically positioned".

It had four or five drops of precum sliding down it. " Plan B , get yourself position down and wrap your lips around your lollipop use your saliva and wet that shaft up and down but do it slowly. Let's see how much you can get in your mouth. "

I began slipping my lips over and down, I started tasting my precum again. I inched down I guessed 3 inches or so . She was able to view it. "Look's like your doing OK, let's have you try to go further. ". I slowly slipped down but gagged myself reversing away. "It's OK now just try it again, that's what you always told me, isn't it".

I flashed back to the limited

 

The limited times she had succumbed to my requests for her to fellitio me. My past was coming full circle to haunt me. Only this dildo was larger and way longer than ever was. "Remember just relax you always said, make like it's a popsicle, remember ". My lines I had used word for word. " come on try again you just need to relax and adjust to it, slid down slowly ".

I began to ease back down, I felt like gagging again, I paused and it got better so moved down a bit more. "That's looking real good now slid backwards and then down again go really slow ". She had me do it twice more. " that's good you've got it nice and wet. , let's get you turned around and straddled over the mount facing to the foot of bed, I want you're behind aimed at phone. "

As requested I got positioned. "OK, it's time to get you impaled on your favorite cock work it around your puckered hole let's get your twat filled up with you saliva and lube along with that firm cock". I circled the tip around and better the spit a a little oozing lubricant I quickly found it entering me . I sank down all the way.

"How about you , right up all the way. You are getting really good at this. How's it feeling , I mean are you enjoying the no hands aspect?" Well it's convenient and more comfortable in a way. " well get you, your liking this". I just said its easier and comfortable versus twisting to reach.

"Well let's get you pumping yourself on that stud shaft, go ahead test it out. I began to start slow in and out my lifting up and forward pivoting at my knee's. She encouraged me to speed up some.

I was getting a rythm going that was different less on prostate but very pleasant. " Must be feeling nice you are leaking nicely now, take your violet dildo use it to catch your spunk, let's see how wet it gets ". I slid it along the head of my pinke leaving worm trails. I had rolled it and continued.

"Hold that up, its quite juiced up, let's have you clean that up some, get to licking don't let it dribble off. I went to work. She watched. " your developing new talents, I guess you're house cleaning experience is paying off, that violet shaft is spotless ".

"While you're pumping your twat with that hard cock are you satisfied? It's fine my prostate isn't getting the same pressure from this angle but its nice. Just not as intense like this. May I have permission to play with my breasts and nipples? " No, I don't think that's a good enough request description, I told you detailed requests ".

As I was continued in my riding the dildo I rethought my request . May I have permission to pinch and tweak my nipples please ? "Well that's more of a correct request but there is a penalty for failure to ask properly the first time. What's my penalty as my urge to escalate my feelings tugged at my soul.

" well I think if you took your pretty violet cock and gave it some proper attention you might earn a privilege to play with your nipples some".

Again another price to pay merely to play with myself.

 

She knows how much my breasts and nipples have become hypersensitive these days. They always were a magic connection to my groin but the gynecomastia elevated them to extreme sensitivity. A primary factor that put me into bras and even now for night silicon forms to cushion and spread weight.

She restricts and limits them from contact except when she chooses. After being protected by bras and padding constantly when allowed out they react quickly to anything touching them. A fact she well knows and uses now to manipulate me.

Now during my 12 days of penance it has become a fulcrum to introduce me to my own precum and taking dildos into my mouth so two holes are filled with silicone.

I gave in again to my urge to play with myself so I inserted the violet dildo in my mouth wrapping my lips on its shaft. I was still pumping myself in my backside.

"Very good, Alright you may play with your nipples with one hand but I want you're other to hold your violet cock while you're working to suck and lick it, maybe you might try taking more of it in".

I began manipulating the purplish silicone as I tweaked and pinched my nipples alternating left and right. I began to match my mouth plunge with the plunge into my twat. Not the length but direction in and out. I was concentrating on my feelings in nipples that seemed to connect to my balls I was rocking and angling my leg positions and my prostate got more pressure. I felt like I needed to pee but knew it wasn't real. I lost track of my other hand and it's contents.

Apparently she was aware that I was lost in my activities. " My Sweetie what's with you? It brought me back to earth as I opened my eyes and thought about what all I had going. I felt my face flush. "Why don't you take the cick out of your mouth for a moment and tell me what you're thinking about ".

I removed my slobber covered violet shaft .
I am not really thinking of anything I was just riding the feelings of everything, guess I kind of zoned out. "I think you're still zoned out, why don't you stop pinching your nipple and take a break from pumping that cock in your twat ". I was still going at it like auto pilot, well I don't stop or change stroking until you tell me to. "Well I wasn't telling to mangle your nipples like a mad man and I told you to stop ramming your twat and your still humping ".

I froze, she was right I was still pounding myself and I released the pressure twist pinch I had on my right nipple. Between stopping both I felt a loss I had been in a sweet blissful mood. opening my eyes and her putting on the brakes had me kind of crashing down.

"You realize you're supposed to be doing penance these 12 days for a stupid decision to work two weeks in a row including weekend. " I know, I messed up, am doing everything your asking of me.

"Oh., your doing everything I'm asking that's fully evident. It's all the unasked things and the apparent pleasure you're getting. I thought making you experience pursuing the course and lame comments you used on me over the years would be embarrassing and repulsive to you. It very much appears your enjoying all this".

I thought you wanted me to enjoy and even see if I could climax sometime from my prostate play. "Penance is punishment, your not behaving as someone being punished. Take your violet cock and rub some of your precum on it, there's plenty all over your balls."

 

I immediately started swiping it along the tip and rolling it along accumulated spunk around my ball sac. She wasn't joking about the accumulation there. I held it up to phone for her review, I had to keep it rotating so things didn't drip. I already anticipated her next comment, I was close but wrong. Expected her to tell me to lick the lollipop clean.

" Well since you were doing so well taking that deep into your mouth earlier why don't you suck it clean this time your spunk is mostly on the top half anyway, remember like you told me think about sucking a popsicle .

The sting of my word's coming back at me, I really had said those exact syllables. I told her I probably couldn't get to it all since it was probably 4 inches down the shaft.

"You best stoo talking and use your mouth and lips before it slides down another inch, your wasting time and it is running down that shaft ". I flipped it upside down quickly. She laughed. "Sweetie your too late, get it in an start cleaning, you can lay on your back but I don't think its going to change the distance much".

I flipped back on the protective pad and began inserting the purplish shaft. I quickly got another taste of precum as it dropped further in. " Sweetie your lips are dragging the shaft your loosing some spunk, catch it with your tongue, I felt it slide onto my upper chin. My tounge was able to collect it.

"Go ahead you need more depth you can do it, earlier you had it past halfway in, of course you weren't thinking about it as you pinched your nipples and pumped your twat. Take it in suck it clean use your lips and tongue :

I managed to slip it further into my mouth, I rolled my tongue and lips to clean the flexing shaft.

"Very good you polished that shaft nicely, you can let that cock out, unless you want to suck it some more".

I quickly removed it and set it down on pad. " oh that was quick didn't you enjoy that ". No I am only trying to fulfill your directives. " My maybe that's tonight's penance unless you want to clean the Matador off? God no, your joking you know where it was. " Certainly I watched you plunging it in and out off your twat as you rock and rolled around. I guess I will allow you to wash and sanitize it instead. Your done tonight I hope you will remember Mother's Day!.

 

Well she is training me in ways let say directions I did not imagine. I am beginning to think I unlocked pandoras box when I went into locked in cage.

I was and am committed to the journey as long and far as she wants it. In my mind she is my KH even if they just set on her shelf. I have offered her all control on her terms.

I just stopped for night. She calls in 20 minutes. I don't know what she's planning. She told me to arrive before noon tomorrow no excuse for tardiness.

Pace yourself getting back to work.

I have loved some of this but parts are not fun I am adjusting .

 

Monday the 8th day of penance

She texted me a note about Monday since I had told her Monday & Tuesday were training presentation days on split shifts.

Your requirements are for under my clothing.. panties with pads front and back, bra and thigh high compress stockings both days. Also I was to be up early and inject 2 lubes and insert my butt plug for the whole day. I should carry a empty zip lock bag in case of emergency need to remove plug but permission must be granted prior to removal otherwise a penalty would be earned. I also had lube and syringe along in separate black vinyl bag if needed.

I had spent time and worn at night so was not to concerned a large portion of day I would be standing and walking around in office. Pads in panties are not detectable. My biggest thought was if a bowel movement came up. I have already learned that when your backside is being filled with lube later on it comes out and has definite effects on your stool conditions.

She informed me she would be texting random requests to send photo proof of plug in position. I would need to send within 5 minutes of request or I would be in trouble.

Monday went fine no upsets. She called and discussed my day and wanted to know how much I leaked on both pads.

She gave me no other exercises other than sleeping in plug as well. The next morning I had to remove and renew my lube .

Tuesday the 9th day of penance

Was pretty much a duplicate during the day other than I had to call and get permission for a bowel movement urge. I took my lube kit bag out of computer bag to go to restroom with me. Took care of business then replenished lube and replaced plug. Went through a good bit of TP but had some of the Summers Eve wipes they really helped. They are now always going to be along in case this occurs again.

During the recap that evening she reminded me how I had balked about have the wipes in my computer bag and felt them unneeded. I told her in the future I would always have them and also in the syringe kit bag for lube use as well. " Women learn early to be prepared for many things and accidents, you must as well".

That evening after removing the plug she put me through a short length trying out the new vibrator prostate massage unit . The battery and power did not hold up long it was removed and finished with the old nexus hand operated. She allowed me to sleep without the plug that night.

 

Wed the 10th day of penance

Dress code was panties , compression pantyhose, bra under work clothes. I had to exercise extreme care during the entire day not to expose anything and the heat was not fun at all. Comfortable was no where to be found.

That evening she had me rig up the dildo mount but with the smaller violet cock on the mount. As I used it to pump my twat she had me give attention to the Matador, tonight just fondling it , licking and a few plunges to practice not gagging when putting it in further.

I was not allowed to play with my chest at any time. As she put it " You get to carried away when you start playing with your boobies and nipples". I was more than disappointed.

I had a 5AM schedule the next day so she let me off easy.

Thursday the 11th day of penance :

I found myself humping Polly with my cage in place. I was forbidden any contact with my chest or groin. After I was done to her satisfaction she had me install my butt plug to sleep in .

 

Friday the 12th day of penance

Worked early till after lunch before starting part of the drive home . I had been told to stop early enough to accept my last penance session. I was also told to be home Saturday before noon because I had errands to accomplish. That meant being on road by 5AM.

I got some takeout supper for hotel to reduce time. I texted her I was available I requested that we wrap whatever she wanted me doing tonight by 10 pm so I could close out and get some sleep before my early start.

She video called and her first remark was " I would not be dictating when we would finish anymore than I had anything to do with what I would be doing , my only requirement was to execute my instructions promptly. "

With that I merely said what do you want me to do I have shaved everything and showered and removed my cage dressed in panties and sleep top. I have everything ready to go in toys , pads and lubes.

"Very good, I see you prepared you strap on mount let's put your violet cock into the harness but reverse its curve direction tonight ". That was a surprise change. " get a condom on that shaft so you can settle your sweet twat down on it, but before that I have something else for you to accomplish. Move around so you can take it into your mouth to wet it down and practice getting more in". I began lowering my mouth down over the shaft. It tasted different or I guess the condom did along noticed a different feeling with the stretch of latex.

She orchestrated my movements for up and down along with speed from stopped to moderate up and down. She occasionally prompted me too go further down. I was getting less gag feelings as I followed her guidance. She decided it was time to change"

" Well I know you're enjoying yourself but you're twat needs some exercise". I wasn't enjoying myself. "Sure you're enjoying it, look at your almost semi hard leaking pinke, it says your excited, that I believe. not you're words". Again my pecker was
was peeking out and showing some small amount of a semi hard condition, for me that is rare these days.

She had me put in two lube shooters of lube then added some with my slobber on the condom. Then I spun around and began to get it started into my sphincter. The reverse bend was odd, I started sliding down onto it and got a very different pressure onto my prostate. I quickly realized I just put out a spurt dollop of precum. She saw it " Wow, what was that, a mega spurt of spunk".

I guess, I've had that before sometimes. "I think that was the biggest dollop you ever spurted with any penetration ". The dildo turned put more pressure on my prostate ". "First, do not refer to to your cocks by anything else except maybe pet names , you like naming body parts . Look at the protection pad see how much it was? There was about a dime size little area where it landed probably double or so over usual deposit when it happened. I figured all the edging and stimulation had built up to make it happen.

She started me into motion the reverse bend was changing the feelings as it slid in and out as I pumped myself on it. My pinke didn't change during all this it kept what little growth it had. I held back asking for any fondling permission. Again she ran me through a series of different motion patterns. I dripped additional fluids at times it was changing from thin to thick and clear to milky. I had not really noticed that before.

As I pumped she remarked " take your Matador and dip it around in your spunk I think you're ready for a lollipop ". I did as directed I was curious in a way since before my juices were generally milky white. I knew my dipping sauce was mixed in both.

After collecting I brought it up and slipped into my mouth. She began instructions on how and what to do with it. It tasted similar but it was slightly different and the viscosity changes I noticed as well. I continued following her instructions as I filled both holes as directed. I did not have a clock viewable as time passed. I knew my jaws were beginning to ache. She had be remove and dip the Matador two more times to renew my flavoring as she called it.

She finally had me empty my mouth and asked " would you like to suck that cock some more or stop". I said stop my jaws ache. " don't worry remember you told me it gets easier with practice when I was blowing you when you insisted I try". Again my history was being used against me.

" Well I guess you're not interested in earning chance to play with your breasts tonight " I had willfully avoided asking for permission tonight now she dangled a carrot in front of me. It's not that I mean last time. I already did more with that cock than before. " That's true you sucked and licked much cock tonight but you didn't ask permission in advance and it wasn't your task to earn playing with yourself. you were just building stamina and technique to suck your favorite cock and taste your spunk ".

She then again changed my rear stroking pattern. I was debating asking for permission to fondle myself. May I play uh may I pinch and tweak my nipples while I pump this cock my twat.

"No, I think not, it's getting late I believe its time to wrap up"

She had me slide up off the violet cock and start my clean up. She inspected my replaced cage and reminded me about not being late getting home and not to cheat with any fondling of myself.

She then asked " has this 12 days of penance taught you anything about your behaviour current and past,? Think about that we will discuss it tomorrow in person, ".

 

Saturday I arrived ahead of schedule after an early start.

My offer to take us all out on my return to celebrate Mother's Day was moved fro Sunday to Saturday by my wife. So we the kids and granddaughter headed out about an hour after I arrived. My wife just told me I have other plans this weekend for us felt we would get this out of the way so we would be unhampered.

She had told me I had several missions to accomplish this weekend. Monday and Tuesday had Doctor visits as well.

I needed to discuss my needing to drop to Missouri next week. I had worked out with customer to get down Tuesday evening after Doctor appointments. Plan is to return Friday evening. I decided to tell her in person rather than phone. I know she wasn't going to be thrilled. I miscalculated her reaction a major error .

After lunch we broke off kids went home while we drove North to start farm store where she wanted too go. As she looked at clothing for her and granddaughter. My job was just tag along patiently. As we chatted I decided to update her on the changes next week that has me back out rather than home. As I informed her that I would be rolling out Tuesday after Doctor was done. She looked at me with a very scornful look, she remarked " you better be joking and it's not funny ". Honey I'm sorry but it's not a joke with the Ohio 2 week run it's the best option to catch up commitments. She said " Just hush, go wait in car. I will finish my shopping and be out, we will finish this conversation in private ".

I headed to the car knowing I was going to catch hell with her. I knew by her facial expression I just dug myself another hole. She had just spent 12 days in penance sessions for a bad decision. This weekend she already had plans to finish in person what had been started via video call sessions.

 

Well she came and sat down in car. I apologized again about adding a trip into schedule trying to get caught up.

She remarked " you just came off 2 weeks away solid and 12 days of penance to remind of how bad your decision was. Apparently the penance exercises made little impressions on you"

Oh no , I know I messed up and you were sending me messages on my errors, you demanded me to do things outside the box.

"Sweetie apparently you enjoyed yourself being outside the box, I think penance turned to pleasure for you. Rather than to emphasize you were being reprimanded apparently you were getting enjoyment.

No I was not enjoying what you demanded that I do. I am really sorry.

"You haven't begun to be sorry , I am going to change things so you apparent thick skull will learn when I am dealing with your failures" " right now drive us to Joslyn's shop, you have shopping to do".