All She Needs to Do is Ask

I felt my body moving without my being aware of it. Grinding against the two toys in an almost vulgar, instinctual fashion, hips writhing, sounds I didn't know I could make sliding from my lips. I was embarrassed of course - I'd heard plenty of locker room talk by that point in my life, slurs about gay men taking it up the ass, sissies and queers - but I also couldn't stop. I started to feel more and more ashamed, doing this in front of her. Really for doing any of it at all. It hit me all at once, the extent of what was happening. Here I was with my girlfriend, my cock locked into chastity, being ass fucked, and I was not just allowing it but encouraging it, eagerly yearning for it like some animal. I wanted it, I needed it, it felt so incredibly good I couldn't stand it. I was torn, part of me dying to cum, the other never wanting it to stop. What kind of man was I?

And that's about the time I came. I felt a wave pass over me like nothing I'd ever felt in my life, my cum spurting out over the bed, my legs, her hands, and somehow even a few drops on my own face. At first she was surprised. It was quite unexpected after all. There was the suddenness of it for one, along with the dramatic reaction of my body, thrusting up, back arched, clamping down on the toy. But first and foremost was the fact that it had happened at all, with me being completely locked up, my cock not having been touched even once. She quickly shifted over from shock to utter delight. She was captivated by the event, fascinated by the fact that such a thing was even possible for me. She couldn't stop talking about it, not just while I was cleaning up, or for the rest of the night, but for days after it happened. She was entranced. And what that meant is she absolutely wanted another performance.

After that everything else I could have done became unsatisfying for her. That's all she wanted anymore, for me to come without being touched, still locked up. It got to a point where the chastity cage simply never came off anymore. Not for any reason. Months went by without me ever touching my own cock. I even had to research how to clean it without taking it off. Her expectations for me were as high, and this was no different. She always held me to those kinds of standards, just like she had for all aspects of her life. She wanted the best, and wouldn't settle for anything even vaguely disappointing when she knew she could have something bigger and better.

I want it to be clear, this wasn't a punishment or anything, it wasn't like I was forced into it. I just allowed it to happen and never said anything otherwise. I had this nagging fear that if I ever spoke up about it that would be the end of it. It was a silly thought, considering how sweet she always was, but I couldn't shake it. I also didn't want her to worry, or to be unhappy, or to feel let down by anything I did. Nor was there any need to trouble her with my complaints. She has an intense dislike for whining. Don't get me wrong, she'll listen attentively if I ever broach a problem with her, but only if it's with the intent of finding a solution. She has no patience for pointless kvetching. I don't blame her, it's a waste of time and serves no purpose. It just leads to a sour mood, and who would want that? In any case this led to my never expressing even the slightest bit of potential displeasure. I didn't say a word about having to deal with chafing, or how it fit in my clothes. I wouldn't have dared, in case she got the wrong idea. She was so sweet to me, I'm sure she would have offered to remove it, maybe even insist, and I absolutely did not want her to have to go without something she loved so dearly.

But her peculiar notions for me didn't stop there, either. As I said before, she's a very doting girlfriend. She loves to coddle and pamper me, and she'll praise me and shower me with affection - though I must admit it sometimes makes me feel more like a fancy show poodle than a boyfriend. This trait of hers only amplifies whenever I please her exceptionally well in the bedroom, or perform a task above and beyond her expectations. I legitimately crave these bouts of gratitude and affection, and strive hard to earn them. I know for a fact that they aren't just her attempts to manipulate me, but are true earnest examples of her love. In fact, no one else I've ever known has made me feel as loved as she does. That's the honest truth. All I can do is work as hard as I can to show her I am worthy of it. To please her in every way I can. She really is that amazing.

I will openly admit, however, that sometimes her ways of showing affection could come across as strange to a more mundane audience. For instance, she really likes buying me gifts. When she's pleased with my performance, whether in the bedroom outside of it, she'll shower me with presents - but the ones she gives me aren't things most people would ever consider buying for their boyfriend. She prefers getting me things that are cute or sexy and specifically dislikes things that seem too macho or manly. At first I expressed a bit of concern about some of her choices, especially when she started buying me things like, say, thigh high stockings or baby doll crop tops. She eloquently pointed out that society had unfair gender expectations, and that people should wear whatever they wanted and not unthinkingly bend to the judgment of others. Of course she was right. She always is.

She further explained to me that the things she bought me were boy's clothes by the simple fact that it was a boy who was wearing them. She expressed, again and again, that she wasn't dressing me up like a girl and she certainly had no desire for me to be one. What she wanted me to be was a pretty boy. She found it attractive. And, well, it's not like it hurt me to do chores in skirts or lace panties. It made her more likely to do delightful things with me, whether sexual or simply sweet, doting, and romantic. She'd slide her hands over my clothes, into the stockings and up the crop tops, steal kisses in the kitchen or even jump up on the counter so I could get her off before breakfast. So, truth be told, I sort of leaned into it. After a time it even made me feel sexy because she found it sexy. It made me feel desirable, even loved, and I wanted more of that.

In time I even began to like the feel of them on my body. The way the soft stockings felt when I pulled them up over my shaved legs. The way the shirts fit me, clinging to my chest, how I looked in sheer hose. The way the skirts and thongs reminded me of just how exposed I was, especially when I was scrubbing the bathroom on my hands and knees, how easy it would be for her to come up and take me from behind - a thing she did not infrequently. She'd just pin me down and have her way with me, getting herself off by pegging my ass with a vibrating double sided dildo she'd fit into a strap on before leaving me alone to finish my work, still wet and dripping, with the added bonus of now having to clean the cum off the tile as well. If she was in a more sadistic mood she'd have me clean it with my tongue, panties still down, her rubber cock still in my ass, grinding her hips against me.

I didn't really need the gifts, not really, but they were this kind of physical signifier that I was pleasing her. So I kept doing the things that got me gifts and, better yet, her praises. I'd do her chores, wear the clothes, give her pedicures and massages, cook her favorite meals. Especially after I moved in with her. I worked from home so I'd even do my job wearing a more casual outfit - like daisy dukes with a tight flannel knotted in front. Or sometimes even in nothing more than lacy negligee and a pair of garters and stockings. A couple times she even had me sit on a vibrating massager while I was trying to work just so she could watch my cock strain at the confines of the cage, never receiving quite enough juice to get me off.

I could tell she was in a really good mood when she said she wanted to actually see me get off. She would have me fuck myself in front of her, using one of our toys in my ass, sometimes with a vibrator latched to the cage - which always remained on - perhaps kneeling on the carpet in front of her, cock dripping, while eating her out, or even, embarrassingly, spread legged on the glass tv table, everything on display like a museum piece. When she was in a really good mood, she'd even do it herself. She took immense pleasure in stretching me and seeing just how much I could take inside me, little by little. I can't lie, I began to crave that feeling of being completely filled, to feel her pushing the toys in and out of me over and over again, fucking me hard, grinding it into my insides and pushing them up against my prostate. Even though I felt ashamed, spread out and moaning like some needy slut, I just couldn't get enough of it. I even felt turned on just knowing how taboo and debased it was, the shame itself fueling my hunger. I'd be near falling to pieces from embarrassment yet still be very eager to continue, unable to stop. Sometimes she'd stop and ask if I needed to quit, or if I didn't like it, and I'd begrudgingly admit how I actually loved every second of it and would beg and plead for her to continue again, to keep going.

She decided she liked seeing me embarrassed like that, the way it looked like I couldn't stand another moment while simultaneously getting increasingly excited by it, my body responding to it almost against my will. She had me do more and more things just to get me flustered. That is to say she expressed that she'd like seeing it and I couldn't help but give her exactly what she wanted. She really enjoyed putting me in awkward or ridiculous situations, weird predicaments designed specifically to make me squirm, and it got worse and worse over time. But I was rapidly becoming a glutton for punishment, even as I felt the layers of my pride and manhood being stripped further and further away.

I could give you a million examples of the things she did. She'd peg me up against the windows, my body pressed to the glass in full view, or on webcam for strangers. She'd truss me up like a turkey reading for stuffing on the dining room table, or string me up from the ceiling in shibari, or tie me up on the bed and make me beg and plead just to pleasure her. She would make me go shopping with vibrators taped to my thighs, or balance a tray of drinks on my back while she watched TV, or sleep in the closet, or clean her feet with my tongue before doing her nails. She'd sit on my face and put on a movie, or keep me between her legs while she ate a meal I'd just cooked her. She'd put a vibrator on my chastity cage and rub her clit on it until she came, leaving my own cock hard and aching. She'd even attach a vibrating dildo to a chastity belt, facing outward like a proper dick, and ride that while my cock was locked up inside. She had me wear a plug and keep clean so she could peg me whenever she got in the mood, even if I was in the kitchen cooking or trying to do the laundry. She would tease me while she did, saying that she had to train my ass very well so she could use bigger and bigger toys, that if she was going to peg me then she wanted to have a huge cock to do it with. She even filmed and took sexy photos of us for an onlyfans account, more enjoying the attention and perverted comments that flooded in - and the way I agonized over the exposure - than whatever money came from it. She really got off to being admired and lusted after. Sometimes a purchase or a hot comment would have her seeking me out so she could talk about it while I went down on her.

Just recently she invited a friend over for lunch, and, since I hadn't been informed she was coming, they walked in while I was cleaning the living room in a cute little lotita dress my girlfriend had bought me. The skirt barely covered my ass cheeks and if I moved at all you could see my panties and bowed garters. Her friend saw me, of course, and I was absolutely mortified. I wanted to run and get changed, but my girlfriend, probably seeing how flustered I was, invited me into the conversation so that I couldn't bolt for cover. I had to politely join in while they talked about a new sweet shop that had opened up downtown, and then the small boutique next to it.

This was incredibly different than doing such things in front of strangers. Having someone there, in person, and someone I personally knew, was filling me with so much shame I thought I would die. I didn't understand how her friend could just keep casually talking like that either, like nothing was going on. Eventually the conversation rolled around to me and my dress. They went over all the little details, the trimming, how it fit me. I felt very put on the spot, especially as they started talking more about my body than the dress. Over time more and more indulgent details started finding their way out of my girlfriend's mouth. The two of them, to my utter horror, even lifted up the front of my dress to take a look at my cage tucked so neatly into my trimmed panties. I wanted to bat their hands away, to cover myself, but my girlfriend seemed so thrilled, even proud, to have someone to share this with. And I really did want her to enjoy herself, even if it came at my expense. So in the end I let them and kept my embarrassment to myself.

You see, as it turned out, this friend of hers had a particular shared interest, something which they'd bonded over in the past. Namely pretty boys, and especially pretty boys kept in chastity. My girlfriend started divulging more intimate details, egged on by the excitement of her friend - how she used toys on me, the ways she tied me up and how she fucked me. Her friend was eager for details, asking more and more explicit questions which my girlfriend was more than happy to answer.

It was at this point that her friend started expressing how envious she was, how she wished she could find a nice boy like me. She said she'd been single for much too long and it was really starting to bring her down. She hadn't even had a good lay in ages, she said.

It was at this point that my girlfriend suggested something completely crazy. She offered to let her friend have some fun with me, let off some steam. I of course protested. I didn't want to cheat on my girlfriend or anything. I loved her. But my girlfriend very patiently pointed out that wasn't she the one suggesting it and giving permission for it? No one was cheating if everyone was okay with it. There are plenty of people having threesomes and swingers parties so I shouldn't make such a fuss about such a small thing.

Honestly I think I was just really put off guard by the suggestion. I was already embarrassed, and now my girlfriend was talking about doing sexual things with someone I barely even knew. My girlfriend seemed to notice my apprehension, and started running her hands over me, asking me what was wrong, asking me if I didn't find her friend attractive or if I was being too shy. I didn't want to insult her friend, or disappoint my girlfriend, so I finally caved.

I was shocked by how cool they were stripping down into their underwear, complimenting each other on their choices, laughing, like it wasn't anything more than a casual dinner party. As for me, they watched while I stripped down slowly in front of them, into my sheer slip and panties. I kept the stockings on. Her friend sat on the couch and my girlfriend directed my face between her legs.

I got to work with my tongue, gently parting her pussy lips, sliding it over her clit. I could tell she was already getting wet, her taste filling my mouth. I gently worked my fingers inside her while I continued to work on her clit. I could hear her moaning, feel the little movement of her legs against the sides of my head, squeezing me tighter.

And then I felt my girlfriend, pulling down my panties from behind. I felt her slowly draw out the plug that I'd put there earlier that afternoon as she'd directed to do in a text message. I heard - and felt - the little pop as it released from me. I gasped, and I felt her friend pull my face down onto her with her hand, her fingers wrapping in my hair.

My girlfriend then explained to her friend about her strap on. I couldn't see it, but I knew she was showing it off. Her friend was delighted, and I could feel her getting hotter, getting more and more turned on, her body writhing on my tongue and fingers.

Then I felt the cold chill of lube followed by my girlfriend's large rubber cock pushing into my ass. I moaned and gasped, briefly pausing my efforts as I felt the length of it pushing itself inside me. She slowly worked her way in until her hips were planted flat against my ass. She pulled out, making delighted sounds of her own - the other end of the toy was pushed firmly inside her pussy.

Her friend made a soft whining sound and pulled my head again, reminding me to keep pleasuring her, even as my girlfriend started to pound me harder and harder. My girlfriend's rhythm made my fingers push into her friend with every thrust, which seemed to drive them both wild. It was only a short time before her friend was climaxing, forcing me down onto her with both hands, legs hooked around my head as she ground her clit against my tongue, legs quivering. My girlfriend came as well, letting out a large gasp, grabbing my hips and thrusting in hard, her whole body shaking.

My girlfriend at that point popped the dildo out of me and started undoing her strap on. I was confused, but then she pulled me away from her friend and slid her friend's legs open wider. She slid the end that had previously been inside her into her friend's still quite sensitive pussy, making her friend moan and tremble. She helped her strap into it and used a remote to activate the internal vibrator. Her friend gasped in delight, air pulling across her teeth as she felt yet another wave of pleasure.

She then pulled me up, seated me onto the couch, and spread my legs. My caged cock was on full display. Her friend then pushed down on my legs, near my knees, lifting my ass up, and drove the strap on into me, pegging me hard into the couch. She was eager and hungry, even after her orgasm, obviously having been left unsatisfied for quite some time.

My girlfriend of course wanted to give her a fantastic experience, so began rubbing her body and teasing her, even passionately kissing her, their lipstick smearing together. It seemed to drive her friend wild - and make my cock so incredibly hard. I could feel the metal of the cage pushing hard against me as my cock pushed against it, fighting against the steel ribs.

Eventually my girlfriend grabbed a vibrator, pushing it against the cage so her friend could watch my reaction as I came, ashamed and worn out, the cum exploding out and then dribbling down my dick and over my stomach. Her friend came at the same time, the strap on pushing inside her and rubbing up against her clit from the inside. She continued to thrust into me for some time after I came, pushing the dildo into me over and over again to keep her own climax going as long as possible, riding the wave of her ecstasy, some of my own cum getting mixed into the lube and getting pushed inside me as she continued to peg me until the rush of her multiple orgasms finally wound down.

Her friend, quite pleased and pleasantly worn out, thanked my girlfriend for the fantastic experience and started getting dressed. She mentioned that she'd been planning to have one of those tupperware party type events, but with sex toys, and inquired if she might be able to borrow me for the event. She thought it would be a great deal of fun to use me for demos.

Which is how I ended up in a room full of women, all giggling at my nakedness as I moaned and writhed in the middle of a stranger's living room, raising up my ass so I could take yet another toy into me, degrading myself like a complete slut for a full group of women.