Sissy Boy Confessions

[sissyboytanya]

I've spent the last several months becoming my Mistress's sissy slut and I want to share some of my experiences. I'd also like to hear from other sluts like me. I'll tell the story of how I went from mere slave to sissy later but I want to share my most recent experiences (and Mistress approves). I'm a college student so I spend my days dressed as a boy (although I only wear panties under my clothes no boxers or briefs) but when I'm with MIstress I am Tanya. I am young enough and small enough to pass pretty well. Due to school being closed for monday I've spent the weekend with Mistress and will be here till class tuesday afternoon. I'm fairly new to being with men although I already love it and something really strange happened last night. So she had some men over as a treat for me, three guys with big thick cocks, black I think but since I had to spend the entire time blindfolded (dressed in a school girl uniform at that) I can't say for sure. THey were all verbally abusive calling me white trash, and a two dollar whore I spent some time having cocks stuck in my mouth sucking each in turn till they pulled down my panties and two of them fucked my boy pussy (making the third and forth men to do so in my life). When they had cum (two in my boypussy the other in my mouth) they spat on me and smacked my ass before leaving. Sometime later (still blind folded I don't know how long) someone else came in. She was quiet but she guided my mouth to her pussy and made me lick her clean of cum. She then got up and walked out not saying a word. I was left alone for the night in my little room (not really a room just a spare store room at Mistress's place she set up for me pink and frilly with twilight posters and my little pony figures around, and yes I hate twilight thats why MIstress did it). In the morning I found a note on the door and a silk nightie (Mistress gets full control of what I wear when we're together) the instrucdtions were simply to dress and join them for breakfast. Putting on the red silk nightie and satin panties I went down to breakfast expecting my MIstress and her room mate to find my twin sister had come to visit. My family is very conservative sis is the only one who knows about Tanya although she loves me as the sister she never had (our older brother is another story He'd beat me down if he even suspected). Both of them were sitting there talking and shut up real quick when I came in looking at me my hair and make up a mess from the night before and trying to hold back giggles. We had breakfast and sis asked about my training and if I still liked being a girl still holding back laughter. THey've since gone out shopping with instructions for me to start this thread and be ready when they get back. What i don't know and am nervous about is who was it I cleaned up last night? I though it was MIstress but now I don't know, I suspect Sis was at least around to watch but I don't know that either. Whats really sort of weird is both ideas are turning me on. If only I was permitted to touch myself without permission.

 

[sissyboytanya]

More to share from last night. So Mistress took me out to a adult book store with a couple glory holes (second time). She dressed me up in what I can best describe as hooker wear. Tube top, micro mini, fishnets, high heels to much makeup. My sister came along as well and yeah serviced a series of men, could even hear a few asking how much to fuck my pussy. I took several shots in my mouth and three on my face and then had to go to the front and buy condoms with cum running down my cheek from a guy who barely looked old enough to smoke. Got home and was told to put on pig tails and footie pjs. Tied up again, blindfolded again but this time an anonymous blow job and snowball/make out session. I'm more then a little convinced it was my sis now specially since she apparently is now Mistress's new pet. Oh and sis apparently also had a booth to herself last night.

 

[RedStarFic]

Sooo.. this is kind of hot. I might be checking in on progress here from now on.

 

[shelbakk]

Fantastic experience! I can't wait to read more.

 

[sissyboytanya]

So went to a sports bar tonight with sis and Mistress as a final test. Flirted with guys, got drinks from them and even made out with one. When I asked permission to suck him off I was denied. As punishment for being a whiny bitch about it sis took him to the apart onstead. Now locked in my little room listenong to sis and Mistress moan, Mistress brought one back too, forbidden to even touch myelf. I wanna cry I'm so horny.

 

[shelbakk]

More more more! Love this thread

 

[sissyboytanya]

So was collared today. Sis was there, sje serves to now, and watched me get fucked by the same guy who was my first fuck. Sis got a strap on from our Mistress at the same time which was soooooo hot to watch. After the guy filled my boypussy with cum ais and I 69ed for their amusement and yes snowballed me my own cum

 

[sissyboytanya]

So I thought i"d tell the story of how I became a sissy slut.

I met Mistress my first year of college she is older but was taking one of my classes. We started talking after class one day and became friends. I was attracted to her from the begining and she knew it but it didn't go anywhere. Well sorry to say I wound up embracing the stereotype of a young kid from a conservative family away from home for the first time. Meaning I got drunk and smoked a lot of weed. My grades started to slip and Mistress made me an offer, get my shit together and she'd go out with me on a date. I didn't want to flunk out and she was gorgeous so I cut back on the drinking and smoking and got my bum to class on time more. When I got an A on my next test she took me to dinner. She picked the resturant, paid, drove and pretty much ran the show (in retrospect it was probably a clue) and at the end of the night kissed me on the lips (no tongue but it was a good kiss) and said if I kept it up we'd do it again. Its not as melodramatic as saving my life but I owe her a lot and its why as slutty as i am I"m very loyal.

Dating eventually moved onto sex (this happened naturally not as bribery) and from the start she took control. Her on top, her deciding where and when and gradually she started working dominant elements in. I've always been submissive I let my sister pick most of the games as kids, played dolls with her and was never big on the sports thing. She got me to dress like a girl the first time by making me a bet. If I did it and it didn't turn me on she'd invite a girl to have a 3 way with us. I was a typical guy so I said yeah. From the moment the panties enveloped my cock I couldn't deny any more I liked it so she started dressing me up as a girl teaching me how to act, walk, talk, do my makeup and so forth always promising she'd give me the girl on girl if I went along. Eventually we graduated to butt plugs and in time she decided I was ready for my first strap on. Just before she did it she brought me in front of a mirror fully girled up, squeezed my ass and told me "see you got your girl on girl action" which still both makes me laugh and gets me hard to think about.

The toher thing she was doing at the time was sucking me off and then feeding me my own cum. I found I liked the taste and in time she graduated me to sucking cock and then of course to getting fucked. Its been about 6 months now and I'm proud to be Tanya I never want to go back to being just a shy awkward "straight" boy.

 

[shelbakk]

Has your mistress introduced you to BBC yet. Would love read your first real cock story

 

[sissyboytanya]

She has not although looking forward to when I get the chance. The first cock is a fun story but I think I'll do the first time I got fucked (same guy).

My Mistress has a fuck buddy who's bisexual. Not a submissive of her just someone she screws when she needs a man's attention. We'd met before and I liked him (still do) so she thought he'd be the right choice. A month or so before I sucked him for the first time and he was perfect. He took it easy with me, let me find my pace and even warned me when he came. Yes I swallowed that first time I have done, and love, facials but my favorite is a mouth full of spunk to me its the reward at the end of the hard work.

He came over one night when my Mistress said I had earned my first real fuck. I'd been begging for it for some time but she kept insisting I wait. I dressed up in a very short skirt, blouse and seamed stockings. I was already lubed up with a butt plug in place to keep me ready for him when he came by. I was nervous as hell when he showed up not meeting his eyes or saying much wanting what was coming but just spooked and he put up with a while the two of us sitting on the couch with Mistress watching. Then he started kissing me. Pushing me back against the couch groping me, squeezing my ass and telling me what a cute little slut I was. I started moaning and my hand found his bulge stroking him feeling him grow hard and listening to him moan. I knew he was ready but I wanted one more thing first. I got down on my knees and pulled his cock out sucking him while he sat on the couch caressing my hair calling me a good little slut. After a time he pushed me back and said it was time and Mistress handed me a condom and tube of lube. I slid the condom over his cock and lubed him up and he pushed me down onto my hands and knees. He laughed when he saw the plug and slipped it out using his fingers to apply more lube inside my boipussy making me moan in anticipation. ONce I was ready he slipped into me working slowly coaching me through it till he was finally inside me taking time to let me adjust before he started to thrust groaning about how tight my cunt was. My own clit was jumping around at this point hard and leaking the whole thing making me crazy leaving me moaning and begging him to use me. It didn't last long and soon he was spurting into the condom and sliding out. As a last gift, with Mistress's blessing he set me on the ground and licked my clitty till I told him I was about to cum when he left me to spurt all over myself. Mistress insisted I use my hands to clean myself up and of course I had to lick my mess clean. The whole thing was one of the most erotic experiences of my life and I am very greatful to him (and always to Mistress) for being the one to make me a full sissy.

 

[turnofthepaige]

Thank you for sharing all of those experiences Tanya. That is wonderful that you found such a sexy Mistress who allowed you to discover this side of yourself. I wish I had discovered these desires at such a young age when I'd have been much more passable than I am now. You sound like you have such hot times ahead of you and hope you continue to share your stories

 

[Wantstotryit]

.....

.....

 

[Wantstotryit]

yes

It would be fun to get used by a few guys treating g me like a whore....so hard now

 

[shwetaCD]

It would be fun to get used by a few guys treating g me like a whore....so hard now

Totally I wud bring my mom too

 

[sissyboytanya]

Wanted to check in its been a while. I'm under punishment at the moment. The other day at a gay bar I kissed a man without permission so no touching myself or any other guys for a month (would have been a week but my whiny mouth got me in more trouble). Mistress has promised me my first bbc at the end provided my grades for the semester are adequate.

 

[sissyboytanya]

Mistress has been botj kind and cruel today. I moved in today, well sat around in a hello kitty t and short shorts while real men moved my stuff in. She was kind because after cuffing and blindfolding me the men got to fuck my face and boy cunt. got cum in my mouth and cunt but wasn't allowed to cum. It was after all about thanking them for helping not my enjoyment. The teal cruelty was inviting a black friend od hers over later. Mistress sucked and fucked him while I had to kneel in the corner and watch. She didn't gag me and my begging got another week added to my punishment. Now laying on my bed wishing I could stroke myself in a silk nightie.

 

[sissyboytanya]

Mentioned on another thread being forced to masturbate for Mistress and her friends so I thought I'd share an example.

Second night at my new home Mistress had a girls night. Sis was actually there forced to be naked but otherwise part of the chat and I was dressed as a maid and running errands: drinks, food nothing particularly sexual. I had a plug in and when I brought MIstress her second beer was ordered to turn around and bend over. She of course pulled down my panties to show off my plug and then told me to lay down on the coffee table. I did and I was ordered to play with myself. Conversation continued around me the women mostly ignoring me except for the occasoinal glance till I got close which is when Mistress ordered I stop and get more appetizers. After giving me time to calm I was made to start again while they all continued to talk and get drunk then to stop again and get them more beers. Finally I was allowed to cum in my pretty black panties and forced to lick it clean then sent to bed after a swat on the rump from Mistress.

 

[shwetaCD]

I wish someone would force me to masturbate.. I've got a candle for a dildo right now.. Never done this before

 

[shwetaCD]

I wish someone would force me to masturbate.. I've got a candle for a dildo right now.. Never done this before

I'm gonna imagine this candle to be ur cock! Tell me what to do!
Kik BShweta