Quickie

My GF was able to come over to my apartment today for me to cook her lunch. I noticed when she arrived that she wasn't wearing her necklace with the key like she always does. I asked her and she told me she was in such a rush to leave this morning she forgot to put it on. "Besides," she added with a teasing tone, "I don't have time to unlock you right now, anyway." After we had eaten she told me she wanted to cuddle for a bit before she had to leave to go to her afternoon appointment.
We were cuddling in bed, talking about our plans for the rest of the week when she sighed and said, "I wish I had more time. I really could use a good orgasm right now, but I only have 10 more minutes before I have to leave."
I said, "If you like, I could at least make good use of my mouth and spend that time trying."
"Ok! And maybe if you do a good enough job I'll bring the key with me when I come back in a few hours," she said with excitement, before winking.

I then proceeded to do as a good boy should. She was able to orgasm three times, in between grabbing my hair and saying things like, "You're such a good boy"; Make me come, now!" and "I love making you do this while I have you locked up." I absolutely love when she praises me for a job well done.

She had set a timer on her phone so she wouldn't be late, and had her final, massive orgasm just as it was going off. I held her legs and arms as she shuddered in ecstasy. She pulled her pants on while I sat on the bed grinning. It makes me so happy to pleasure her. She walked over and gave me a kiss as she grabbed my crotch, then whispered in my ear, "Maybe I'll bring the key with me when I come back. And maybe, if you're able give me a repeat performance, I might just unlock you."

She hugged me and left, both of us grinning. She was physically satisfied, and I am emotionally satisfied, though the strain against my cage is a reminder that her satisfaction always comes first.

 

So to continue from where I left off:
My GF did come back over to my apartment after her appointment. Once she got in the door, she immediately said, "I think those clothes should be off. Like, right now."
I smiled and obliged, and we made our way to bed. I jumped into bed and under the covers. It's been in the single digits here (Fahrenheit) and the bedroom is always kept on the cool side. She stood beside the bed and looked at me with a mischievous smile. "Yes?" I asked.
"These clothes of mine won't take themselves off!" she said.
Once we were both disrobed, she told me to take a step back, "I need to take a look at my little guy down there. Hmmm, he's nice and snug, now isn't he?" she asked teasingly.
We were both smiling and I replied, "You can't blame me. I do have an amazingly beautiful woman naked in my bedroom."
She looked at my and asked slyly, "And what are you going to do for this amazingly beautiful woman?"
"Whatever she tells me to do."
She smiled wide. "Good answer!" and she pushed me onto the bed.
We dove under the covers and I immediately began kissing her all over. She was moaning with pleasure, grabbing my shoulders and scratching my back. "Oh, you're such a good boy. Yes, keep doing that!"
After a while she gently pushed my head lower and I of course knew what to do. I don't know how may orgasms she had and I don't know how long I was pleasuring her. The entire time I was straining against my cage. Eventually she pulled me up to her and kissed me and told me what a good boy I was. "Anything to make you happy. I love you!" I told her.
She took off her necklace with a smile, holding up the key, "Maybe I should use this. What do you think? How bad do you want me to unlock you?"
"Oh my god, I'm so desperate. I want you so bad. Please, please, please!"
She giggled and said, "I want you too, so you're in luck."
She unlocked me and we had the best sex we've had in weeks. I somehow managed to keep from coming for more than 15 minutes. After a very powerful orgasm, she was panting as another orgasm built up. She said, "Baby! Oh, good boy. Come for me, come with me!" We exploded together, holding each other tightly. It was mind blowing.

Afterwards we were both exhausted and ended up falling asleep cuddling. I woke up an hour later and realized it was dinner time. I gently left the bed and went to wash up and start dinner. She woke a few minutes later and walked up behind me at the stove. She wrapped her arms around my waist and rested her head against my shoulder. "You know I love you. You're the best!"
I turned around and we held each other, "Yes, my dear. I love you, too. I couldn't have ever dreamed of how much I love you."

She told me later that night that she wanted me locked up again. I asked her if I could have the night off, which I almost never do. She asked me why and I told her that with the cold weather my skin was a little chaffed and a night to re-coup would help greatly. She seemed a little disappointed. "Are you sure you really need to?" she asked.
"You know I would never ask unless I did." She knows I have a huge threshold for pain and discomfort, and I can endure quite a lot. But she's also told me that she doesn't want me to "push through the pain" to the point that I might cause myself damage, even if it was just raw skin.
She told me she wanted to have a look, and I showed her where my skin was red and sore. She agreed that a night to recover was in order. "But," she added, "You better lock yourself back up first thing in the morning."
I smiled, "Yes Ma'am."

Today, she had appointments all morning again. We had planned on spending the afternoon together, but she was asked to babysit at the last minute. She did make it over to my apartment for a late lunch. I made turkey bacon cheddar paninis and chicken noodle soup. I must admit, it was delicious.
In between appointments this morning she sent me a text message telling me she wanted me to put in my butt plug two hours before she came for lunch. Since it's our last week of winter break before we start school again, I think she's trying to make sure we make the most of it. Once classes start up next week we won't have as much time to "play" together. Which of course is lucky for me!
Just as we were about to sit down to eat she told me to go take out the butt plug. I returned a few minutes later and we ate.
"So how are you feeling, love?" she asked me once we had finished eating.
"I'm doing pretty good today. I had a good night's sleep last night."
"That's good. But I meant more like, how's your bum feeling," she asked with a smile.
I giggled, "Like it wants more!"
She sighed, "Well, it's too bad we don't have more time. I have to leave in 30 minutes. I think we should cuddle."
As you might have been able to guess, we both absolutely love to cuddle. We lay on the bed for a while, talking and cuddling. We talked about the upcoming FFF and how excited we were to go. As the time approached that she had to leave to babysit, she said, "Take your pants off. I need to inspect." We both smiled as I obliged.
She told me to get on my hands and knees on the bed. She gently tugged on my cage, "You're a good boy, all locked up for me."
"Yes, of course my darling," I said with a smile.
She began to gently rub my bum, then I felt the cool lube. She said, "Shhhh, just relax."
I could feel the plug as she began pushing it into me. I moaned with pleasure. She told me what a good boy I was. Suddenly, she pushed with much more force. I yelped with surprise as the entire plug was pushed firmly inside me. she held it in place and asked, "Are you ok? Do you like that?"
"Mmmmm, yes I do!" I told her.
"Well, that's good, because this was going to stay in here whether you liked it or not," she laughed and playfully spanked me. "Ok, you can pull your pants back on now."
We smiled at each other. "Yes Ma'am," I replied.

So now I'm sitting here, locked up and with my biggest plug inside me, waiting for my GF to get back from babysitting. She was told by the parents that they would be home around 10ish, so I have another 5 hours or so to go. And I can't complain. I'm a lucky boy!

 

I definitely believe my GF has been trying extra-hard the last week to make sure we “get it all in” before the semester starts. Yesterday was amazing, we both pulled out all the stops and had what she refers to as ‘marathon sex.’

She came to my place again early in the afternoon, after a lunch meeting with a friend. She arrived around 1 PM just as I was making myself lunch. I finished and quickly ate while we chatted, and then she said we should cuddle for a while because she was cold. Naturally I agreed.
Once in bed I told her that I had found a video earlier that I thought she would be interested in. She’s a very visual learner, so I had been looking for a good video of a guy in a humbler being fucked with a strap-on. She said, “I’ll watch it in a bit. I just want to lay here with you for a while.”
We both knew that we would be having sex that afternoon, though it is always up to her the ‘style.’ I knew she was struggling feeling a little overwhelmed by the looming semester, so I just snuggled into her and we talked quietly for a while. She loves how I snuggle her, and it almost never fails to turn her on and help her forget the pressures of everyday life for a little while. And I love it too, so we’re a perfect fit.

Sometime before 2 PM, I could tell she was finally feeling a little livelier, and she said with a smile, “Ok, I wanna watch some porn now!”
I pulled my laptop onto the bed and played the 5 minute clip I had found. She didn't say anything but I could tell it turned her on. She was smiling, and when she starts to get turned on she wiggles her hips and generally can’t keep still. Once the video was done she looked at me with a big grin and said, “Play me another!”
“Well, I only bookmarked the one. Do you want me to find something right now?”
“Yes, please! I really liked that one. I’m getting horny!”
Up until that point I wasn't extremely aroused, but her big, devious smile and telling me how horny she was caused me to start straining against my cage.
I smiled and looked quickly for a video of a tease and denial, something else we had talked about but she had never seen before or really understood. It was a forgettable video- not very well made but it gave her the general idea. It was 20 minutes long, so I just played the last five minutes. She said, “Well, that was kind of bad. Think you could find a better one real quick?”
“I can try.” I knew she was still horny, but I didn't want her to start losing interest so I hurried to find a decent video.
I found one a Mistress “torturing” a man in a humbler equipped with e-stim. Again, something I had told her about but she had never seen. She said it was a little too hard-core for her, but she liked the general idea.
After the last clip she sighed and said in her playfully demanding voice, “You better take your computer and put it someplace safe. This might get rough!”

We had taken off our shirts before jumping in bed, and now she told me to take off my pants. She removed her bra and jeans, and we both stood in only our underwear. Well, I also had my Jailbird locked on, haha. She was wearing a sexy black lace thong. I absolutely love when she wears thongs, they make her bum look so delicious! She looked at me and said, “Ahem!” I smiled and removed my underwear. “That’s better,” she said as she reached down to give me a little squeeze.
We crawled back on the bed and she told me to lie on my back. She commenced to playfully fondle me while simultaneously rubbing my perineum, slowly circling closer to my hole. If not for the Jailbird I would have been rock hard.
She was kneeling on my arms, facing away from me. I could still move my arms from the elbow down, so I was rubbing her and caressing her everywhere I could reach. I felt on my chest that she was extremely wet, and she was grinding into me and getting wetter. She started to gently push on asshole, massaging it back and forth with her finger. All the while she was moaning and saying things like, “Do you like this?” “You’re my good little boy, tell me how much you want me,” and so on.
After she had her fill of teasing me, she started to get up and told me, “Ok, now that I've spent some time spoiling you, I think you should do the same to me.”
“Yes, Ma’am!”
She lay down on her back and told me to make her feel good. I know all the right places that really turn her on. I really went to town, kissing and sucking and stroking and grabbing in all the right spots like my life depended on it. I could tell she had completely soaked through her panties so I reached to pull them off. She beat me too it, tearing them off and then pulling me towards her for a long, hard, passionate kiss. I wrapped my arms underneath her and kissed then gently bit her neck and she came hard.
I’m super lucky to have a GF who pretty much can cum at the drop of a hat. It doesn't take much to get her to come, and we have yet to go long enough to find the end of her ability to orgasm.
When we first started dating I remember going down on her for an hour at a time, giver her orgasm after orgasm, one right after the other seemingly with no end in sight. I only stopped when she had to pull me off her because she couldn't catch her breath and was exhausted. I would lay gently on her as she shuddered and trembled, orgasming just from the pressure of me on top of her for another few minutes. She would be ready for the next go around after only 15 minutes or so, and we’d do it all over again. Lucky for her she can climax so easy, lucky for me I can’t help but want to make her come as much as she can stand.

Once she came several times from my kisses and hands, she told me to go lower. She said, “We’ll see how much you make me squirt, and then if I think it’s enough I’ll let you squirt later.”


TBC

 

Continued:

The first time she had an ejaculation, we were both surprised. It was a few months after we had been together and she didn’t know anything about female ejaculation. It was actually before I had even told her about chastity. To be honest, it had never happened to someone I was with before. I was fingering her and lightly put my tongue on her clit and all of a sudden I had a face full of come. It took me by surprise and I jerked my head back slightly and the stream went right up my nose, lol. I quickly realized what was happening and carried on with what I was doing, just making sure my mouth was there to catch all of it.

So when she challenged me to “make her squirt,” I smiled and decided I’d give her the ride of her life! Almost every time with have sex or I lick her she squirts, but she says the best orgasms for her are when she comes the most. Sometimes it’s a little bit and sometimes it seems like gallons upon gallons. We’ve learned to be prepared and lay towels on the bed before we begin anything since we quickly got tired of sleeping on a soggy bed.
I gave her everything I had, using all the tricks I’ve learned over the last several months of being with her. I hit all the right buttons in all the right ways and she came bucket loads. The most she has ever come since it first happened. After a while she was panting and having one orgasm right after the other, unable to stop. In between, she was saying, “Ok! Ok!” and pulling at my shoulders: her signal that she needed a quick break. But I know from experience with her when to listen and when to ignore her pleas and continue. I could tell the orgasms we just getting better and more intense so I kept going. I wrapped my arms under her thighs put my hands on her belly and held tightly as my mouth worked furiously.
It took several minutes before I could tell she had peaked and the orgasms, while still very powerful, were starting to wane. I waited until the orgasm she was having slowed, and pulled my face from between her legs and looked up at her. While trembling and shuddering (what I like to think of as ‘after-shocks’ lol) she made a motion with her hand for me to come up to her. I pulled my arms from beneath her legs and lay on top of her, supporting myself on my elbows as she panted, trying to catch her breath.
I was smiling down at her, proud of the job I had done and incredibly horny. The cage was really starting to get uncomfortable as I strained against it. Once she had caught her breath she said, “Wow. Oh my god, you are such a good boy. That was so good. It was just, I don’t know, it was just……wow.” She laughed and kissed me, pulling me beside her.
I lay next to her, holding her as she was still breathing deeply. I couldn’t stop smiling. She looked over and smiled and said, “I think I need to cuddle for a while. You wiped me out!” She turned on her side and we spooned. She sighed contentedly and I held her. We chit chatted for a few minutes.
Finally she said, “I think you deserve something special after that awesome performance. What do you think?”
I said, “Maybe your strap-on?”
She giggled, “I know you want sex!”
“Well of course I do! How could I not want to have sex while I’m lying next to a beautiful, sexy, naked lady?” I replied.
She laughed and said teasingly, “I think you deserve some sex. You should get my harness out for me.”
I got up and went to the drawer where I keep our toys. I took out her harness and held it out.
“Um, and the dildo, too!” She said.
“Which one would you like to use, my darling?” I asked, smiling.
She smiled, “I’ll let you decide this time.”
I took out my favorite dildo and put it on the harness. I asked her if she would like me to help her put it on. “Yes, you should help me.”
Once she had it on she lay in the bed on her back. She patted the bed and told me to lay down, she still needed a bit of a break. I lay next to her and she admired her cock. He wiggled her hips, smiling at how it waved in the air. She playfully stroked it. “You want this, don’t you? You want to have sex?”

I finally realized that the sex she had been referring to was her fucking me with her strap-on. She very rarely teases me or taunts me with the possibility of denial. But that’s because she wants to have me inside her once she gets warmed up. So I was surprised and more than a little turned on. I guess what I thought had been a boring video clip had planted the seed in her head, and she was toying with the idea.
I said, “I want you to fuck me, then I want to fuck you.”
“Well!” she said with a mischievous grin, “The first one is definitely happening! We’ll just have to wait and see about the rest.”
I pretended to groan, “I don’t know if I could take that!”
She retorted, “You will if I tell you to!”

I was pleasantly surprised with the attitude. She’s become more and more confidant in her dominant role in the bedroom, and our sex life has really blossomed in that regard. We still have “vanilla” sex more often than not (if you can consider me being locked up in between as ‘vanilla’ lol) but when the mood strikes her, she is much more sure of herself ‘ordering’ me around. It’s wonderful. When I first introduced her to chastity and femdom she liked the idea and was excited by it. But just like anything new, it takes practice to get the hang of it. There were times it seemed forced or contrived, but we always kept a good sense of humor and carried on and learned from each other and about each other.

I hated the concept of topping from the bottom, but I was in the strange situation of being the one who was much more experience with sex, especially kinky sex. I had to somehow introduce things to her and explain ideas and possibilities without seeming demanding or that I expected her to do exactly what I had in mind. Over time she has taken my various fantasies, added some of her own, meshed them together and created wonderful situations and scenes. In essence, she has taken my fantasies and remade them in her own image into *our* reality. I could never have imagined how wonderful it would be, or how much I love her and adore her. She’s perfect for me in every way.

TBC

 

Continued:

She looked down at me locked up and straining in my cage. Grinning she asked, “Getting pretty tight down there aren’t you? I bet you wish I would unlock you?”
“Yes Ma’am,” I said. “It’s getting rather uncomfortable.”
“How much do you want me to unlock you?” she teased.
“I’m not sure how much more I can stand. It’s almost unbearable!”
“Well, I’m feeling generous. I guess you can be free. But don’t you dare try anything funny!” she said.
“I won’t!” I promised. She took her key and unlocked me, gently releasing me from my prison. She stroked me slowly a few times as she set the Jailbird on the dresser. I asked her if she wanted to lube me up or if I should do it.
“I think you should do it. I want to watch my boy touching his ass!”
I reached in the drawer and pulled out the lube. She said, “Uh! No, you need to stand up and give me a good view!”
I smiled and stood next to the bed. I bent over and asked, “Like this?”
“That’s better. Now lube yourself all up, nice and slow.”
I did as I was told. I started to slip a finger in and she swatted my hand. “Time to get back on the bed. I’ll let you decide what’s most comfortable for you. This might take a while!”

This is an example of how we’ve grown over the last few months. I know that she still isn’t completely sure of herself while using the strap-on. She’s concerned she’ll go too fast or too deep, or too slow and at the wrong angles. But instead of fumbling around like in the past and then having to ask me what’s best, she incorporated that into the scene. Pretending that allowing me to decide the best position was her way of being gracious and kind to me allows us both to interact with our fantasies while maintaining our realities. She’s in control of the situation, allowing me to give her input while still maintaining her dominance.

I suggested that I start out by riding her while she lay on her back. She said, “Good idea, that way I can still relax and fuck you at the same time. You’re such a good boy keeping me in mind.” In reality, it had been a while since we used the strap-on and I just wanted to take it slow and control the pace. She knew this, but instead of us having to verbalize this she twisted the idea and turned it into part of the scene, that way we were both still turned on. She still felt in absolute control, I still felt dominated, but we approached the situation with reality in mind. We’ve learned that if we push the fantasy to hard, reality won’t match up and it will be very unsatisfying.
I slowly lowered myself onto the strap-on. She began slowly stroking my cock as I slid further down, finally taking the whole 9 inches. She said, “Good boy! Now I want you to grind on my big cock.”
I did, feeling the dildo moving inside me, waves of pleasure washing over me. Grinding against her harness started to make her climax again.
I began to bounce up and down, slowly at first and then harder and harder. Each time I was lowering myself down she rose up to meet me, grinding the base of the dildo onto her pussy. As she got closer to orgasm, she let go of my cock, completely engrossed in her own pleasure. She came fairly hard, though not as hard as when I was using my mouth. I pushed down fully, grinding back and forth as she came.
When she had stopped, I asked, “Please, will you fuck me?”
“Yes! Get on your stomach!”
I lifted myself off her and lay back down, lifting my ass into the air. Head down, ass up as they say, haha!
“You want my cock, don’t dirty boy! You want me to fuck you with my big, hard, black cock? Tell me how much you want it.” She said seductively.
“Please! Please fuck me! Fuck me hard, I want it so bad!” I begged.
She slowly put the tip to my asshole, gradually putting pressure until it started to slide in. She stopped half way and waited a moment. “More!” I begged, pushing back.
She started to fuck me, just barely moving an inch or two in and out. It was driving me wild! I started to buck, begging her to go deeper, harder, faster. She picked up the pace and fucked me until I squirted. It wasn’t an orgasm, just an ejaculation, but that very rarely happens to me. I think I can count on one hand the times I’ve ejaculated from anal stimulation alone. Usually I have to stroke my cock and stop just before I orgasm, and the cum just dribbles out without any orgasm at all. Still very pleasurable, but not as good as a full-blown orgasm.
But this was different. It was the first time it had ever happened while she was fucking me with her strap-on. When she saw the small pool of cum, she quickly slowed down and pulled out. “That was really good. Did you like that?” she asked.
I felt shaky and weak as I rolled onto my back, “Oh my god, that was awesome! Thank you so much my love!”
She smiled wickedly, “I’m glad you enjoyed having sex!” She took off the harness and quickly lay down next to me.
I laughed. “Maybe I’ll just have to get you all horny again!” I started to caress her all over, slowly inching my hands lower and closer to her pussy.
“Well, if you do, that doesn’t mean I’ll let you come!” I was so turned on I couldn’t help myself. But the idea of being so horny and then locked up again was almost too much. I decided I’d just continue and hope for the best.
I used my fingers until she came several times, then started to crawl on top of her. “Uh, uh! No you don’t mister!” She pushed me back and got on top of me. She lowered herself onto me, just barely grazing my cock with her dripping wet pussy and then grinding her clit against it. I was trying to angle my hips to slide inside her and she deftly would move, letting me get close but never inside. She was smiling at my efforts, teasing me horribly. I gently placed my hands on her hips and tried to nudge her so I could get inside her. She pulled my hands off of her and put them behind my head.
“Bad boy! If you move your hands again I’ll have to stop! Understand?”
“Yes Ma’am, I promise I won’t move my hands!” I pleaded.
“You better not! For your own sake!” she said.
She was grinding her clit into the base of my cock, her ass just barely caressing my cock. She leaned forward to kiss me and her hair fell in my face. This is not at all an unusual occurrence, and without thinking I reached up to brush it to the side.
She sighed and slumped beside me. “I told you not to move your hands.”
“Wait!” I protested. “That doesn’t count! I was just moving your hair, that’s not fair!”
“I told you not to move your hands and you did, so I guess we’re done.” She was smiling.
“Please one more chance?”
“Ok, but you better not move your hands!” She climbed back on top of me.

TBC

 

Continued:

This time she didn’t tease me long. After a few moments she slowly began to slide onto me. She shudder and came, pushing herself fully onto me. When her orgasm passed she whispered, “Don’t move a muscle!”
I said nothing as she slowly raised herself and then lowered herself back down, pausing and grinding slowly into me. It took all my effort not to move and raise my hips. She leaned forward and whispered in my ear, “Good boy.” She kissed me before sitting back up and doing it again, excruciatingly slow.
Grinding down onto me again, she came hard. She began to pick up the pace, again telling me that I better not move a muscle.
She rode me until she began to orgasm over and over, grinding down on my cock as her pussy pulsed around me. Finally she told me she wanted me to fuck her. “I’m going to lie down now, and you better fuck me like you’ve never fucked me before. I want it slow and hard!”
She climbed off me and lay on her back. I got on top and slid inside her, doing as she told. Slow and hard is always the most difficult for me not to come. It was especially difficult since she had been teasing me mercilessly for what seemed like eternity.
I fucked her the best I could, and she was orgasming deep and hard, her entire body convulsing with pleasure. I couldn’t last any longer. I whispered in her ear, “Please may I come?”
“Good…boy…come…with…me!” She sputtered in between shudders. I picked up the pace and she started to scream. She was grabbing my shoulders pulling me tight to her as I erupted inside her. It was a massively powerful orgasm, and we came together, holding each other tight.

As the Third Eye Blind song goes “Later, bathing in the afterglow…”

When we had both caught our breath and calmed a little, I slid off her and lay down next to her. She stayed where she was, legs splayed, hair everywhere, eyes closed and mouth agape. I snuggled up against her and put my arms around her. She puckered her lips and I giggled and gave her a kiss. She patted my shoulder, “Good boy. Good boy.”
After a while she opened her eyes and looked at her watch. “Holy shit!” She laughed, “It’s 5:45! What time did we start?”
I told her I couldn’t remember exactly. “Must have been around 2 or so.”
She laughed, “That’s ‘marathon sex’ right there! We’re awesome!”

I couldn’t agree more

 

Thank you, Sir That means a lot to me. I'm hoping that I won't be too busy to post more now that school is starting up again tomorrow. It probably won't be as wild for the next few weeks, but I do want to start posting my thoughts here more regularly, sharing the journey that my GF and I are on together. And I hope that you continue to enjoy reading!

 

Since I hope to be posting in this thread as my journal/blog I thought it would be appropriate to give some background info.

I’m 25 right now, and pursuing my undergraduate degree. I’m a little bit older than most college students, (and much, much wiser I’ve found) and that’s because before going to college (or uni for my friends across the pond) I was in the Army for 6 years. While in the Army I served 2 tours in Iraq for a total of 26 months overseas.

“What the hell does that have to do with chastity?” you may wonder. Well, it gives you a vague idea of who I am as a person. I am a real person and chastity is a real part of my life. But it is only a part, not the whole; but as a part it affects the whole. Also, the converse is true: everything else in my life has some effect on my chastity.

Chastity is not some external entity that is only what it is. Once you incorporate it into your life, it becomes yours. Personal, intimate, unique. There certainly are similarities and hence this community where we can share our individualities and learn our commonalities, or in other words the similarities in practice and technique.
Please forgive me if this sounds wordy. I’m not trying to sound ‘high-minded’ or anything like that. I’m just trying to concisely state my opinions and views.

So back to me. How did I first become exposed to chastity and chastity devices? The interwebs of course! I was probably 14 or 15 when I saw the movie “Road Trip.” Here is the clip that led me down this rabbit hole:


I had been playing with anal stimulation for about 2 years at that point, and like most boys growing up in a closed-minded, strict and religious household, I was ashamed of the fact. When I saw that movie it was a huge eye opener. The character being milked is the typical ‘all-american’ male: slightly chauvinistic, sexually closed minded and extremely heterosexual. At the time, a character type that I could identify with. I wanted to be what I thought of as ‘sexually-liberated’ just like that character: able to be confident and sexually aggressive, maybe even predatory in the sense of going after what I wanted. (Not in the sense of taking what I wanted, to be clear)

But then he has his prostate milked by a nurse AND LOVES IT.

“Whoa, whoa, whoa. Isn’t that gay? Isn’t taking it up the ass totally homo?” I thought. Well, one thing I knew for sure was that the character definitely wasn’t a homosexual or even slightly bi-sexual. So it was like a hit over the head: I can enjoy fingers up my ass and still be hetero. A huge sigh of relief for me, as I was always ashamed of myself whenever I masturbated, let alone enjoyed a little anal stimulation with my fingers.

And so I googled ‘prostate milking.’ One of the pages I found was a detailed description of a milking ritual to be followed with a man who was locked in chastity. I’ve looked for the site more recently and I can no longer find it. I delved further into the web, searching for all the info I could find. I remember being incredibly turned on by the prospect of being denied orgasm and only milked.

I learned about FemDom and chastity and chastity devices. At the time it was all just a fantasy, and the opportunities I had to search the web in privacy as a teenager were few and far between. Months would go by before I was able to get back online and try to find the websites again. Since we only had one computer in the house I always had to remember to delete the browser history, etc. or risk my religious and strict parents finding out, and with very slow internet back then I only had small tastes before I had to stop or risk being caught.
As I said, I was around 14 or 15 at the time. I eventually just let it go, leaving the fantasy of chastity to fall into the back of my mind, and eventually be almost forgotten.

When I was 18 or so, I ran across something on the web that reminded me of chastity. By that time I had much freer access to the internet and was able to spend more time routing around the internet letting my fantasy grow and become stronger. In the meantime I joined the Army, and when I was 19 was shipped overseas for the first time.

 

I came home when I was 20 and for the first time rented an apartment of my own. That’s when I became more serious. I started buying toys online, not having to fear my parents accidently opening a box to find a dildo or butt plug. I still struggled a bit with my sexual identity, but I was no longer perplexed about it like I was when I was younger.
Pretty soon I bought my first chastity device, some leather contraption that obviously didn’t work very well. The longest I ever had it on was a few hours. I delved more into CBT and explored that for the most part, as I was hesitant to shell out the money for a real chastity device, but I always really wanted to.
I finally bought the Birdlocked mini, which proved to be impractical for me. But since I didn’t have a keyholder anyway, I played with it every once in a while wearing it for a day or two at a time before I got too sore and the chaffing became unbearable. I joined a few chastity communities, and had several online keyholders from time to time. I was deployed again when I was 22 and spent another year in Iraq.
I got home and started to go to college when I was 23. I had more money and eventually bought a CB6000s. I began to wear it for longer and longer periods of time, sometimes with the help of an online KH, but mostly self-locked. It was an up and down thing. I would go many weeks locked with some short breaks, and then not at all for a few months.

My girlfriend’s screen name on here is Growing Curious, so from here on out I’ll refer to her as GC. We met just over a year ago and have been dating for 9 months. She was pretty inexperienced sexually. We didn’t have sex for the first month of our relationship. I would use my mouth, and to toot my own horn, quite effectively
Several times she started to reach into my pants and I stopped her. About 3 weeks into our relationship she asked me why I didn’t want any reciprocation. I told her that the first time I came with her, I wanted to be inside her. Intercourse-wise, she was still a virgin, though she had been active in plenty of other ways over the years. She didn’t quite understand why, since all the guys she had been with up to that point had always been more interested in their own satisfaction rather than hers. I, of course, am the complete opposite.
I explained to her what erotic anticipation was, and she understood a little. GC is the type of woman who when she wants something, she wants it NOW. She hates to wait. I told her that for me, waiting just made it that much sweeter. That really turned her on, and it was soon after that that she decided she was ready to give me her virginity.

She loves sex, and can’t seem to get enough of it. Which is awesome for me. At the beginning I could barely keep up with her. Over last summer I only saw her 3 days out of the week and by the end of those 3 days I was more than ready for a break from sex lol.
She is very curious and loves to try new things. I introduced her to some light bondage, erotic massage, and very slowly starting dancing around some concepts in chastity. We talked endlessly about sex and I would sometimes drop hints like, “Do you know what a strap-on is?”
She would say, “You mean like a strap-on dildo?”
“Yeah, you know some guys like that kind of thing.”
She would ask, “Have you ever tried it?”
“No.” A lie. “But maybe someday. Who knows? I’ll try anything once.”
“Yeah, I don’t know if I’d be into that kind of thing. Sounds kinda weird.” She would say.
I’d agree, knowing that once the seed was planted she would think about it every once in a while, and either bring it up again for discussion or decide that it definitely wasn’t her ‘cup of tea.’
At the beginning she never decided something didn’t suit her. She was always willing to try new things. She wanted to try some anal play and I gave her some things to read. We went toy shopping, and I confessed to her that I had used dildos on myself in the past. She was a little more interested but wanted to take things slow. We bought a few tiny dildos and plugs to use on her to see if she liked it.
She really did. She also started to let her fingers wander during sex and play around with my asshole a little bit.
Once I knew that she really was open to new and ‘weird’ things and not just saying so like so many girls, I decided I would have to introduce her to chastity soon.

She came over to my place one weekend, instead of me visiting her. We decided to have some drinks, and I had the goal of us both getting a little tipsy. Me so I’d have the courage to show her my CB6000s, and her so she wouldn’t be totally shocked.
When we were both buzzed, but not really drunk, I told her I had something to show her. She was excited, like she always is to see something new and interesting. I said, “It’s really weird. Promise me you won’t run away screaming or anything like that?”
“Of course not. I mean, unless it’s a dead rat or something,” she laughed.
“Oh no, it has to do with sex. Kinda,” I said.
“Oh! Show me, show me, show me!” she said with excitement.
“Ok, I’ll be right back.”
I brought her the little black case the CB6000s comes in, and let her examine the contents. It didn’t take her long to realize it had something to do with a penis. I told her it was a chastity device. She didn’t quite understand so I offered to show her how it went on. She smiled and said, “This is so cool!”
I put it on and clicked the little lock shut. I held the key. She said, “So wait, now you can’t have sex or anything. It’s locked in a plastic tube.”
“Right,” I said. “If you kept the key, I wouldn’t be able to have sex or masturbate or even get a complete erection until you wanted it unlocked.”
Her eyes opened wide in realization and our conversations about erotic anticipation came to mind. “Just like you said about wanting to wait because it makes it that much sweeter?”
“Exactly.”
She giggled and reached out to fondle me while locked up. “You look so cute! I like it.”
I was incredibly nervous. My hands were shaking. “Really? You don’t think I’m a total weirdo?” I asked.
“Who cares if it’s weird? Maybe it is a little, but that doesn’t mean I can’t like it. And I love you and nothing you could do would make me think you’re a weirdo.” She had been sitting down, with me standing in front of her. She stood up and kissed me and hugged me. I relaxed a little. She whispered in my ear, “And besides, seeing your penis locked up is making me super horny.”
I smiled, “Would you like me to keep it on?”
“Just until we finish our drinks and go downstairs, then I want to have some really awesome sex!” she said.
I pulled up my pants, “Ok. Do you want to have the key?”
“You can keep it for now,” she smiled at me mischievously.

The next day I made her favorite breakfast: French toast and bacon. As I was cooking she sat at the kitchen table and read “Male Chastity: A Guide for Keyholders.” She kept reading while she ate, and kept reading as I cleaned up and then took a shower. She finally finished the book a few hours later. I was nervous the entire time, thinking “Did I push too far? Is this too much all at once?”
Once she had finished the book she took a long shower. I could tell she wasn’t quite sure what to think about it and needed a long shower to think and process.
After her shower we talked for a few hours. She had a lot of questions. I answered them and told her it was just a general guideline and we could experiment to see what worked for us. She agreed, and said she wanted to take it slow and see what happened. “You know me, I need to go super slow with anything new. Baby steps.” she said.

 

Stay tuned! I'll be updating with our adventures over the past few weekends soon

 

So two weekends ago, the 16th – 17th, GC and I went to Providence, Rhode Island for the Fetish Fair Fleamarket. It’s an event generally held twice a year here in New England, with classes, parties, demonstrations, workshops, and of course tons of vendors. The FFF is put on by the New England Leather Alliance (but the event is for Fetish in general) so a good chunk of the vendors sell custom leather goods. Lucky for us we live in New Hampshire so it was only a few hours’ drive for us to get down there. The link:
http://nelaonline.org/cmsms/index.php?page=fff

Ever since I first heard about the FFF I’ve wanted to go, but never had the courage to go by myself. I told GC about it a few months back and she was really excited about it and we decided to go for just Saturday and Sunday. It happened to be on the weekend after Valentine’s Day, so when people (like her parents) asked where we were going we just said a romantic weekend away for V day.
We didn’t stay at the hotel the event was at, but instead got a room at a more reasonable price a short drive away. Since GC is still pretty new to the “scene” I thought going for just the two days would be plenty for our first time. A few days before going down, we looked at the schedule and planned which classes we wanted to attend. Just looking at the class descriptions got GC all hot and bothered
It was an awesome time. We learned a lot and bought some cool new toys. The one she was most excited about was a leather flogger. Saturday night, we used it in the hotel room and I was a little worried we made too much noise, but that weekend there was also some youth hockey thing going on so our hotel was packed with 10-14 year old kids running rampant. I guess the loud kids drowned us out lol. It was fun, but after such a long day neither of us had too much energy to play for a long time. GC had me lick her, and then was so turned on by everything, unlocked me for some intense, albeit tired, sex. We both absolutely loved the flogger and were very happy with the purchase. I can assure you we will be getting a lot more use out of it!

We drove back home Sunday evening in a snow storm but all in all, a successful excursion. There will be another FFF in June that will be in New Hampshire this time, and we plan on going for all three days. I’m sure we’ll have even more fun!

Back home we got down to the grind with our classes, and we didn’t have much time to spend together. But I guess that’s just the life of college students. We try to see each other at least for a short time every night. A lot of the time GC will come to my apartment for dinner and then we will cuddle in bed for 15 minutes or so and chat about our day.

This past Friday night, GC came over to spend the night. We had a wonderful time together and were able to spend the whole day Saturday enjoying each other’s company Saturday afternoon we were talking and I brought up how I had been thinking about how I was kind of interested in diapers. I downplayed it a little because I wasn’t sure how she’d react. She was very happy I brought it up.

At the FFF she noticed every single person wearing a diaper. I only saw one, but while walking around she would lean into me and whisper, “That girl who just walked past us was wearing a diaper! Did you see that?”
I never did notice. “Really? How could you tell?”
“How could you not notice! She was wearing a skirt that barely covered anything and I could plainly see she was wearing one.” she would say with a chuckle.
I would know which person she was referring to, but I suppose it was my modest upbringing that makes me feel slightly uncomfortable to stare. I would notice the short skirt and the pacifier but I wouldn’t let my eyes linger.
They weren’t all girls. The one I did notice was a boy, probably about my age, wearing nothing but a diaper, a bib, slippers, sucking a pacifier and being led with a leash attached to a collar. He was cute, and it made me strain a little in my cage to think of that being me.
I thought it was just the fact that seeing people ‘in public’ dressed in fetish-wear was a bit of a culture shock for her that made her notice every detail more closely than me. (The FFF is a closed event, so you have to be registered to get into the restricted areas which is pretty much the entire hotel. So not totally ‘in public’ but pretty close)

So when I brought up diapers she told me she had been thinking about it for months, on and off. Then we went to FFF and it was the thing that turned her on the most, to her surprise. So it had been on her mind even more last week. It dawned on me that she wasn’t just idly noticing people wearing diapers, but was actually scanning the crowd to find the ones who were because the thought excited her. I was pleasantly surprised.
I sheepishly admitted that I had actually gone to the store and bought some, and had been wearing them at night. She was ecstatic. “Show me!” she said with a huge grin.
I had bought a package of Depends the Monday prior. I had to go to three different places to find the ones with the plastic backing instead of cloth. I mean, if I’m going to wear a diaper I don’t want it to be ‘just like underwear’ haha. Most of the ones on the market today seem to be the pull on variety and it wasn’t easy to find the traditional ‘diaper’ style. But I did find some. I took the package out of the closet, pulled a diaper out and handed it to her. She had a huge smile on her face as she reached out to take it from me.
“Would you like to put it on me?” I asked.
“Yes! I think you need to take your clothes off, like, right now!” she said excitedly.

I knew she had done some babysitting in high school but she told me that she never had to put a diaper on someone. Apparently none of the babysitting included children that were not potty-trained.
Once I had taken my clothes off, she handed me the diaper and told me to show her how to put it on me. I opened it up and laid it on the bed, then lay down on top of it. I showed her how to line up the sides to make them even and then she pulled the tabs snug and secured it on me.
“Now stand up. I want to get a good look at my boy.” She stayed seated on the bed
I stood up and she motioned with her finger that I should turn around. When my back was to her she stood up and giggled. Then she swatted my butt and pulled me towards her, wrapping her arms around me. “You’re such a good boy. You like wearing a diaper for me, don’t you?”
It was pretty intense for me emotionally. “Yes,” I replied, “I do. I’ll do anything to make you happy, my love.”
The diaper made it even more restrictive for my caged cock, but I was so turned on I was straining, thinking about the possibilities.

I have a lot more to write about, but I’ll have to finish later.
To be continued!

 

To continue where I left off:

We cuddled in bed for a while, and then she started to take off her clothes. She told me to start kissing her, and after she felt sufficiently warmed up, to make my way lower.
The whole time since she put the diaper on me, she had started to play the role of “deviant/naughty babysitter.” After she was satisfied (at least for the moment) she told me to lay next to her and we cuddled more.
Once she had caught her breath and felt relaxed, she said, “You know, I think boys need to be spanked. Just so they remember to be good. I mean, it will be good for you in the long run.”
I played along, “I don’t think so. I think you’re just trying to be mean.”
“Oh, really? Well, it doesn’t really matter what you think, I’m going to do what I want to you anyway.” While saying this she had risen to kneel on the bed, and started to rip the diaper off. I was lying on my stomach and reached down with my hands to hold it on.
She pretended to be angry, “Bad boy! Put your hands above your head right now!”
She couldn’t see my face but I was smiling as I said, “No, you can’t make me.”
She sighed and got up from the bed, getting our wrist-cuffs from the drawer as well as our other spanking implements. She secured the cuffs to my wrists and then to the headboard of the bed. “There, you see, I can make you.”
She took the diaper off and straddled my legs. I could feel her wetness on the back of my thigh as she started to spank me with her hand. She continued to spank me, caressing my bum between each stroke. She was grinding herself into my leg, and I could tell she was getting wetter and wetter.
After a few minutes she said, “Say you’re sorry for trying to stop me.”
I was enjoying the spanking, and wanted to see how far she would go so I said, “No.”
She grabbed the paddle and started with the furry side. She hit each cheek about 10 times very hard and told me to apologize again. Again I said no.
She flipped to the leather side and did the same, and again I said no. It was really stinging but I knew with each flinch she was getting more turned on, and even close to cumming a few times.
She hit much harder this time, and it really hurt. On one particularly sharp swat I flinched and gritted my teeth, and despite my best efforts grunted a little. That was all it took. She started to cum. She told me to apologize again, and though I could have said no and taken more, I told her I was sorry.
She reached up and undid my cuffs, then told me to roll on my back. She unlocked me as she said, “Don’t you dare move a muscle. Not one twitch. If you do, I’m going to spank you again, understood, little boy?”
“Yes, Miss.” I said. It was the first time I had called her Miss(her first name) and she groaned with pleasure.
She started to stroke me and it didn’t take long before I was completely hard. She got on top of me and lowered herself down. Once I was totally inside her she looked me in the eye and said, “Remember, not one muscle. Don’t even think about moving your hips or you won’t like what happens.” She started to very slowly move up and down. She leaned forward and her hair fell in my face, which I instinctively went to brush to the side. She immediately stopped.
“What did I say? You’re a bad boy! You ruined it. Turn over right now!”
I was surprised by how quickly she reacted, and did as she said. Playing the part I said, “I’m sorry I didn’t know! You’re not going to put my plug in are you? It scares me!”
She took the hint and I could tell she thought about it for a split-second. “Yes I am. The big one, and you’re not going to like it!”
She told me to put my ass in the air then lubed me up. Going back to the drawer she grabbed my plug. She put it to my hole and I backed into it, so turned on that I wanted it rough. She began to push with a little more force and I pushed back more. She added more pressure and pushed it into me roughly, then quickly grabbed the paddle. Before I could even get used to being full she started to swat me forcefully in quick succession. It didn’t take long before I was flinching again, but still rock hard and horny as hell.
When she finished she roughly turned me on my back again and said, “This time you better not move no matter what. Do you understand me?”
I nodded.
“Say it,” she insisted with a grin.
“Yes Miss ____.”
She got on top of me again and this time rode me at a faster pace. She started to come and I was trying with all my might not to move. I wanted to move my hips so badly.
When her orgasm had passed she told me to start moving my hips. “Go very slow. Nice and easy. Good boy. Oh, good boy. You like this don’t you? You like fucking Miss ____.”
“Yes Miss ____. You feel so good. I love being inside you more than anything.”
She started to come again and leaned forward, brushing her hair aside as she whispered, “Faster. Fuck me harder.”
I obliged and she had a massive orgasm. She then lay down and told me to get on top. “You better fuck me right now. I want it and you will do it!”
Naturally, I complied. We both finished with powerful orgasms. It was an awesome experience role playing like that. Before that day we had never “pretended” by taking on roles just for play, but it’s something I’m sure we’ll do more often now.