The shopping trip

I wrote this today, and I am not sure. I decided to go ahead and post it, I can continue it is anyone is interested. Let me know what you think!

The Shopping Trip

Standing inside the lingerie shop in the mall I am thinking about how good it is going to feel to try on some of these sexy outfits! About the time I had gathered up a couple of things, the cute sales girl must have noticed I had started a collection of things, probably knowing they were not for a wife or girlfriend. She looked to be in her early twenties when she had said hello as I entered the store, I, in my late twenties would have been very interested if I thought I would have had a chance. She was petite with sexy brown hair and a perfectly inviting smile. There was only the two of us in the shop at this time and she asked if I needed any help.

"May I try these on" I said with an I'm sure quite red face.

"Of course, follow me" she led me to the dressing rooms in the back of the store. "Let me know if you need any other styles or sizes, that corset will look very nice on you" she said with a smile!

I thanked her and headed in. My mind took a second to process that this girl seemed to really enjoy the fact that I was about to try on some sexy lingerie. I noticed at that point that my cock was straining in the pink cb-2000 chastity cage I had on. I had just striped down to my panties when she knocked on the door.

"Is everything going ok in there?"

"yes, I think so for now." I said nervously.

"Well, I picked out a few more things I might like to see you in if you wouldn't mind?"

I was very nervous as to what she would think of my chastity, but "I would love to, thank you!" I cracked the door open and she slipped in the door with a few items.

"I had to come in to measure you, but I grabbed a few nighties!" She measured my chest and waist and left in a hurry.

I was left in shock at my good fortune to find a woman who was so helpful, I was wondering if this was partly why she worked at the store!

"Ok, I am back. I was not sure exactly what you wanted to try on, but I brought in several things! I also noticed that era bulge in your panties, are you locked in chastity?"

"Uhm, yes. I well." I was interrupted by her, "who has the keys, I am not going to cause a problem by helping you out am I?" I had to reply, "I have my keys, no problem at all! My girlfriend and I broke up, and well, I just really like to be locked up!"

"Well then, take down those panties and let me see it if you don't mind?" As I pulled my panties down, she got down to my imprisoned cock's level and started to touch around and feel it. "I love that it is pink, I have only seen pictures of them online. So you cant get hard at all or cum can you?"

"No, I can't even get a little hard this thing is so tight. This is not the most secure cage, but it works ok for me because I am not trying to escape."

"I love it! Well, let's go ahead and see how this stuff all works for you!"

I tried on all kinds of things bras, thongs, baby-dolls, she had me try on several corsets and even put stockings on with garters, I think that was her favorite. It took a while, because she had to go check on the store and there were a few woman who came in to shop. Fortunately, no one was the wiser of me in the dressing room. A few times she got back down to check out my caged cock, it drove me crazy to feel her warm breath on it! After all was done she asked me if I would keep the corset stockings and panties she like the most on under my clothes when I left and meet her for dinner! She was due to get off work in about 45 minutes. I of course said I would love to take her out!

We met back up at a very nice restaurant close by. I was very nervous to be wearing the corset mostly in case it showed though my clothes! I was lucky to be wearing a loose button up shirt and jeans, so sitting I bet it did not show at all. It still felt like the whole place was staring at me…

"So, I am sorry to hear about you and your girlfriend breaking up, I did not want to go into it earlier I was so excited to dress you up! How long ago was it?"

"It is ok, I was having a great time too! It has only been a couple months, just had two different paths for our futures."

"And she liked keeping you locked up and dressing up for her?"

"She did, it was not an all the time thing, but she really liked keeping me locked up, and making me wear thongs, lingerie, and butt plugs out and to work."

"So you have worn butt plugs, have you been taken by a strap on?"

"Yes, I love the feeling, but it is at the same time very humiliating to me."

"So if I had a plug with me, would you go put it in for me right now, just a small one?"

"Would that please you?"

"It would very much, by the way, where is your key right now?"

"Then I will do it for you, my key is at home."

"Too bad about your key, but here." She handed me a slim flesh colored plug and tiny tube of lube. "I wear this sometimes to make work more fun" she said. I smiled and excused myself to the restroom. I noticed the plug seemed to be a remote vibrating plug, I have looked at them before, but I slid it in thinking great, I will surely be getting that feeling soon.

When I came back she was ordering a bottle of wine, which sounded great to me at this point! We made general small talk and she never really mentioned the fact that I was now plugged for her. As soon as the waiter brought the wine, the plug came alive, it took me by surprise since I had kind of forgot about it in all of our talking! We were actually getting along great on many levels besides our obvious kink.

"Wow, I thought this was one of those!" She chuckled a little. We ordered our dinner and continued to have a great evening with here turning the plug on and off at her whim. As things were wrapping up, she asked me if I would like to have some drinks back at her place? I said I would love to after she reminded me that my place might not be the safest because of my key being there. I laughed and agreed.

After a short drive with me following her, we arrived at her place. A very nice apartment complex. When we parked and got out, we walked and talked as I followed her to her place.

"Well, this is it!" We walked in to a very tastefully done place. I was kind of surprised as many young woman I meet do not take such pride in their homes. She offered more wine, and I offered to open and pour it. She thanked me and told me that it would be great if I stripped down to my corset and stockings. I blushed a bit and decided it would be fun. As I started to undress, the plug started to go to work again. I looked up at her and she was smiling that beautiful smile she had. I brought the wine, and before I sat down next to her she told me she had a very long day on her feet, I took it as a hint and she gladly excepted. I kneeled at her feet and began to go to work massaging her feet. As she laid back and enjoyed, I took the time to really get into it, as well as taking in the sexy view! I massaged her calfs and noticed that she had on stockings once I saw the garter tabs! That just sent me into a full sub mode for her, I asked if I could give her a full massage?

"You can follow me to the bedroom, help me undress and yes, massage me until I tell you it's ok to stop! Do you work tomorrow?" It was friday, so I had to tell her I had the whole weekend off. "Well, what do you think about staying with me for the weekend, you have enough lingerie to wear for the whole time, you can be my slave for the weekend?"

"Wow, that sounds like a lot of fun! Should I call you, Mistress?"

"That sounds good slave, now get over here and start rubbing! How long has that little cock been locked so far anyway, I can't believe I have not asked yet!"

"To be honest Mistress, I just locked it this morning to go try on lingerie, I had planned to play with it when I got home." I said sadly.

"Well, that is not going to happen now is it?"

"No Mistress."

"What is the longest that you have been locked before?"

"45 days is my longest Mistress, and that was so tough!"

"Well, that is a pretty decent lock up from what I have read about chastity. Would you like me to become your full time Mistress slave?"

I thought for a moment as I made sure to keep giving the best massage I could. "I think I would Mistress, you really seem to be a great person, and I have had such a great night with you!"

"Well, how about you wait to make up your mind until we have spent the whole weekend together, sound fair?"

"That sounds great Mistress, thank you so much for taking the time with a slave like me!"

Mistress then told me she was through with the massage now, and that I had done a great job! She then told me she was very excited from all of this talk and the massage from her new sissy slave! I was told that she needed her pussy to cum, and my tongue was all I had and would have to please her and that I need to get to work to make sure I am worth keeping around! I started to slowly kiss her all up her thighs and work my way towards her beautiful sexy pussy. Finally I started to kiss her gently and unfold her delicate lips with my tongue. She let out a soft moan as she grabbed the back of my head and forced me to start picking up the pace. She came quickly and very intense! I ended up giving her three more very good orgasms before she told me she has had enough for the night! Before she rolled over and fell asleep she went down and kissed my cage. She then cuddled next to me and asked me to hold her. She fell asleep next to me and my head was going crazy with frustration and all the thoughts of this amazing day. I drifted off to sleep excited about what the weekend, and the future may hold for myself and the two of us together.

 

Thank you Mistress Becca!

 

I laid awake for a while thinking of all that had happened. It was a long frustrating night thinking about what could have been if not for this damn cage! I woke early and really didn't even realize I had drifted off. Mistress, seems funny to think that, was still asleep. I went to the kitchen going to make her breakfast! Good thing the fridge had all I needed, because I was not sure if it was ok for me to get out of my corset or put my male clothes back on… By the time I had eggs bacon and a whole breakfast meal about together I heard a yawn and tuned to see a smiling happy Mistress!

"A very good slave indeed it seems I have found!"

"Yes Mistress, I wanted to serve you in bed though!"

"It is ok slave, we have several things to get to today!" she said with a very calm affection that I was not sure whether to take comfort or fear from… "We need to go by your house and get those keys. I want to make sure that I have control over you this weekend, and really, much further as well."

"Yes Mistress."

She ate breakfast quietly as I sat bead hoping it was up to her standards. When she finished, she said that everything was very good and I was to go with her to the shower. She unlaced my corset, and told me to fully undress. I stood waiting to join her in the shower naked all but my cage. After a minute or two of standing feeling very humiliated, she asked me in. Her naked body was amazing! I felt weak in the knees as she took me by the cage and told me that this little toy of a cage was cute, but if I was to serve her it would have to be much more secure. I like my slaves in full belts. I was instantly hard at the idea of this! She noticed and told me that is why, the shemale belts will stop my little cliffy from embarrassing me. After our shower I was helped back into my new corset. Mistress also helped me into my stockings. She came out of her closet with a nice looking little sun dress and helped me into it. I was not sure where this was going, but it was all so great I wanted it!

We left her place and I was feeling quite self conscience about being in full femme with no wig or make up even! We pulled up to my place and went in. Her first words were to get her keys. I did right away of course. She told me not to worry about anything else because she had plans for me! We pulled away and my head was reeling about everything really! She was driving now and within a few minutes, pulled us up in front of a store I was not familiar with. Turns out, it is a friend of hers who has a service of male to female transformations! I was shocked, but very exited. I met her friend and was instantly made comfortable with my surroundings. It was a very nice looking shop, more like a high end lingerie boutique. I was soon in a very private fitting room with Mistress and her friend. Her friend had brought in a box filled with what looked to be all sorts of chastity belt pieces. I was amazed when Mistress used my key and set my cock free. It was just a few sizes of waist belts before they were both satisfied that they had the right one. After that, ice had been applied to my cock to help its aroused state subside. I of course knew that this was not my cage and was serious. Mistress seemed intent on a very high levee of security!

It took just over an hour, but I was now fitted in a very tight very secure full chastity belt that I had no keys for. I felt so good and commented how this belt could probably be worn forever it was so comfortable! I saw both of them smile and realized that might have been the wrong thing to say… That passed over like nothing as they started to go to work on me with make up and false breasts that were glued on. I was scared, but didn't dare say a word for fear this all might end! I had no idea at the time that it would never end!

When I followed Mistress out of the store, I felt so confident as a woman with how they had made me up it was the best I think I have ever felt in my life, and I told Mistress this! She seemed very pleased with how I was taking all of this, and asked me if I was ready to commit to serving her so soon? I thought for a minute as we walked, but I knew I had always wanted and needed this to be happy! I told her I wanted to belong to her and that I did not want to go back to my old life of boring male clothes and having to pretend I was something I wasn't. She stopped and gave me a big hug and told me she was very happy that I feel that way! The pressure felt veery strange on my chest with my new boobs! I also felt myself stir in my belt and there is no where to expand…

Mistress told me she was hungry and we were going to grab lunch before returning home. We had such a busy morning and had been in her friends shop longer than I had thought, I was very hungry also! We had a pretty normal lunch at a very nice cafe, we were away from the other few tables that were there, so I felt very comfortable, that and the safety of my new and beautiful Mistress! We returned home, the whole way Mistress was very kind and kept rubbing her hand up my thigh and touching close to my new belt, it was driving me wild!

"Strip slave" Mistress said in a very firm voice once we were in the safety of her home.

Shaken a little from being so relaxed, "yes Mistress!" Mistress was looking closer at my belt and was rubbing all over saying how great I looked without that ugly male bulge my other cage caused. She then pulled out what looked like another shield to my new belt. There was a very good sized plug on it as well, I started to talk and she smacked my face telling me I was not asked to speak.

"When we are out in public, you might be one of my girlfriends, but here you are mine, and I will tell you when it is ok for you to speak." She lubed up the plug and I was shocked when she slid it back and forth on the way in like she was fucking my ass with it. Then, I heard the lock click and knew there was no release until she wanted. Mistress then told me to go get her a bath ready, she wanted to relax. I drew her a bath and added the bubbles that were sitting next to the tub. She thanked me and told me she was sure I could find her cleaning supplies and to get to work on making her place spotless. I thanked her and closed the door behind me. Still naked My chest looked very strange, but I thought I better not waste any time. I was not sure what Mistress would do if I didn't follow her orders, but I didn't want to find out. I had vacuumed and was on the floor scrubbing in the kitchen when I heard Mistress come up behind me. I looked up to see that she was naked and looked amazing with a large strap on hanging between her legs.

"Get over here and suck my cock." In a very matter of fact way that had me on my hands and knees until I was right under her and sliding her big cock into my mouth. I had never sucked a cock before, not even a fake one, but I was so captivated with how beautiful and in control Mistress was I got really into it! I almost didn't notice she was pulling me towards the couch, she told me to lean over, and I knew what was coming, my first strap on penetration, I felt her unlock and remove the plug, it felt very good to have it come out, but it was short lived when I felt the head of her cock at my opening. Slowly Mistress guided the massive cock into me and I don't know if the plug had made me so horny, but it felt amazing! Mistress heard me moan and started to pick up her pace! This went on for I have no idea how long, but I was spent after and felt like curling up and going to bed

"Ahem." I hear from Mistress as I realized I actually had drifted off for a few! "What about this mess?" I looked down to see I had leaked what looked like cum all over! "You need to clean up your mess slave, also since you came, I expect you to please me as well before you go to sleep!"

"How did I cum? I am still locked in the belt?"

"Never mind that slave, just clean it up and meet me in the bedroom. And, get used to that, that will be your only release from now on." Mistress smiled at me then turned and walked up the stairs. I was left to clean my mess and think about that last statement. And what I was going to do about work on monday? I could not show up dressed as a woman, or at least with breasts on under my male clothes! That was all talked about on sunday where we had a great rest of our weekend together, and I knew and Mistress knew, I was all hers. Sunday afternoon, Mistress removed the breast forms and told me that I was to continue to do everything as normal during the week, but I was to serve her on the weekends. She also told me that I had better be ready to serve her and a few of her friends next weekend for some dinner and some fun. She told me what was expected, and then told me to be there right after work on friday. If I had any trouble with the belt during the week I was allowed to call her and she would have me over to check it out. It had felt great so far, but you never know.

The week passed slowly and uneventful really. I was able to do everything I needed with the belt on, surprisingly! I played with plugs and my dildo's all week to try and get relief, but it was no use. I had to start thinking of serving Mistress and her friends this weekend! Friday I was so nervous, all I could think about was what could I be in store for this weekend! I nervously knocked on her door after work as instructed.

"Hello slave! Good to see you made it back, not that you had a choice if you ever want to have a chance at release again."

"Yes Mistress, thank you!"

"Well, let's get you dressed so you can go shopping for dinner!"

Mistress took me in and reapplied my breast forms and began to put on my makeup. Once all finished She locked in my plug again and got out what I was to wear, a very tight corset with stockings to start, but over that, just a cute little dress! I was pleased that I would not seem to draw much attention, I really did look like a woman after Mistress was all done! Driving to the market with my list was exciting, I was just hoping there would be no trouble if I got carded to buy the wine! The trip went off without a problem, I was shocked that the most that people seemed to notice was getting checked out by a few guys! Mistress really had done a great job making me up! Or people just choose not to make a big deal about what they don't understand.

When I returned to Mistress' place, three of her friends were already there. I am sure I went beat red, but she introduced me to them and they all were very nice! There was a blonde and two brunettes, and they were all very beautiful! I went to work in the kitchen, opening the wine and getting all the girls a glass of wine. They all thanked me and I got to work on making some appetizers and getting dinner going. When I dropped off the starters, Mistress asked me to sit down and join the girls! I said I had a bit of time before things needed checking and sat to relax for a few. Everything went on like I was just one of the girls, and I was loving that no one seemed to be making a fuss over me! I got back to finishing up dinner and Mistress had me sit to eat with them. All the usual girl talk about everyday things went on, still no mention as to me not being a real woman or anything. After we are all done, I clean up everything and pour some more wine. It is then that Mistress tells me to go into the bedroom and change into what she has laid out for me.

I am shocked when I walk in to find only a hood with a ball gag and a note saying I am only to wear that and remove my other clothing and then bend over face down onto the bed. I do this as fast as I can, the feeling the the very tight corset feel great to be free from! A few minutes later, I hear them all coming down the hall, the girls are giggling and I hear them making comments about always wanting to use a strap on on a guy! I feel What I assume is Mistress freeing me from my locked in plug. It feels great to be free from that, but I know it will be short lived, I had no idea how short, as I felt the tip of a strap on right away! I hear the girls laugh a bit and one say "I can't believe how easy that went in, she must love it!" And, I did! It felt amazing to be getting some stimulation! I started to think about, only a week ago I had wondered into that lingerie shop, now here I am living my fantasy! The girls all had a turn, and the laughing really started when they realized that I had cum and it had leaked all out of my belt!

Mistress asks the girls if they had all gotten worked up enough and if they wanted to try my tongue! They all of course did, and the gag was removed from my hood and I went to work for all I was worth to please them! They were all so wet I got as hard as my belt would allow me to! I was really getting into it, when I felt a larger cock than before enter my now well stretched ass! That just got me going even more! After what felt like all night, the girls had all cum several times and the giant cock was removed from my ass! It was another short relief when Mistress locked my plug back in place, this time though I could feel it was much larger than before! Mistress told me that when I heard the door close behind them, I was allowed to remove my hood and get dressed again and meet them all downstairs to thank the girls and see them off. When I got down, they were all hugging Mistress and thanking her for a great time. When I walked in, they all thanked me as well and gave me great big hugs! I felt so happy that I was able to give them all a great night, at least it seemed like they all had fun! Mistress said she was tired, and we went upstairs and got ready for bed. We laid down, and Mistress asked me to hold her, I pulled her in close to me in deb, and thanked her for everything, she wiggled her sexy ass back into me and told me I had done very well tonight, we drifted off to sleep for the night. I knew now I was addicted to this girl and never wanted to be with anyone else.