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Once in a while I become Jill Gossard, a pretty 40-year-old tranny slut. I wrote this story a while ago and first published it on swingingheaven, i have had a lot of meets on that site, here's a tale of one. Last bank holiday weekend I had the house to my self and stayed dressed around the house all day. I spent hours on the Internet looking at pictures of other TVs getting into al kinds of sexy situations. I was going up the wall needing an opportunity to get myself some cock. I had an ad on a swingers website but no one had actually gone so far as to arrange a meet. I then went onto one… Read more

My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to deep-throat his amazing piece of man meat. Once he allowed my mouth to come free -- even for a mere second -- I found myself going crazy. "Oh my god, fuck me harder! Make me your little sissy bitch and fuck me! Fuck me! Oh give me that cock in my mouth. I need more cock!" That I had en… Read more

Went to a family get together at wifes brothers house. I was already locked in chastity from the night before. As I showered my wife got my clothes together, my blue thong and black thigh highs to wear under my jeans and t-shirt. Once I finshed my shower, she took off the plastic lock on my chastity cage (foolish me, I thought she was taking the cage off completely) and replaced it with a small padlock. We both finished getting ready and headed to her brother's house. I had my shirt tucked in, so I was sure no one would be the wiser that I was wearing a thong. My jeans were loose enough that m… Read more

I'd bring you to my bedroom where I would tie your hands together and then tie them to the top of my bed. I give your boobs a good play swirling my tongue around your nipples and gently biting them before moving down. I'd suck on your pussy gently licking before sticking my tongue deep using my fingers to make you wet and dripping. I would then fist your perfect sweet pussy making you moan as you start to squirt. I would take my all ready hard cock and stick it deep in your throat making you gag on it so you cover it in your spit before rolling you over on to your knees and sticking it i… Read more

These are what some sissy faggots said after sniffing poppers for the first time and why they continue to use them. "Yes I have it put me into complete euphoria I love them I became a total sissy fagot when I used them no inhibition. getting fucked and sucking dick in front of others was no problem I became what Ive always been a sissy fagot slut." "when I do poppers anything is possible I b ecome a total cumslut cun t available to be used and filled over and over again the first time I did they before I knew what was happening I was being used by 3 guys as a bitch and I loved it"… Read more

Two weeks went by after my session in the shed with uncle Tony. I was feeling shy embarrassed about sucking him so went out of my way to avoid contact. Was a Saturday morning my mother and aunt heading to mall together. Tony was standing on his deck watching them go. He called over to me "mikey my place five minutes ok? " I just nodded my head yes Five minutes later I was next door standing in his living room. "Come in the bedroom k** I have something for you" he called from the back of house .Uncle Tony had some of my aunt's lingerie spread over the bed. "fix yourself up mikey I'll be waiti… Read more

We started out by chatting on a hookup site. I advertised as a total bottom, shaved sub with a love of crossdressing. He was much older than me, and advertised as a masculine total top. Although he liked masculine boys, he needed his dick sucked badly and we chatted online for weeks, sharing pics and dirty thoughts before we finally agreed to meet at his house. To prep I didn’t have anything for dinner and cleaned out my bottom. I rode my dildo for a little bit and made sure I was lubed up before sliding in a butt plug. I washed and shaved all over so my hole was smooth and left a litt… Read more

This morning I stopped by my favorite tobacco shop for a few cigars. I know the guy who runs the shop is gay (its very obvious) and since I was the only customer in there I started flirting with him. After a few minutes he told me I was serious he had a big surprise for me. I told him that I'm always serious and at that he locked the door and put up a closed sign. He took me to the back room and without any fan fair dropped his pants and a monster 10 inch cock was hanging between his legs. I without hesitation dropped to my knees and started sucking him for all I was worth. I have to say I was… Read more

http://xhamster.com/photos/gallery/4733509/first_anal_sissy_fuck_older_daddy_bareback_cock_cum.html So i organized to meet this guy online late 30s slim build dressed up for him in my  blonde bimbo wig sexy skirt my favorite stockings and skimpy black top makeup done to the best of my ability. welcomed him in take a  seat...he kissed me deep while caressing my girly body i grabbed his crouch massaging through his trousers i unzipped him and pulled his semi erect cock out..oo it was a big cock near 8 inches and quite a… Read more

Using either a finger or a dildo is best. Just place it into your mouth and slowly edge towards the back of your throat. Eventually you will feel it hit the back of your throat where it will trigger your gag reflex. When this happens, hold it there and don’t move it. You now need to maintain your breathing through your nose while at the same time heavily concentrating on relaxing your throat. (Sometimes this is really easy and sometimes this can be quite tough. The key is to keep trying, even if you do find yourself accidentally gagging every now and then.) Hold the dildo steady at the back… Read more

After my first orgasm with a dildo, i realized I wanted nothing more sexually but to be a girl. I fantasized constantly about everything girly: getting up in the morning in a little frilly nighty, spending hours on makeup and painting my nails, silky smooth skin from careful shaving of *everything*, shopping all day trying on cute outfits, sexy outfits and lingere, going to ballet class in a pink tutu and tights...... Not only did I want to do all those girly things, but I became turned on primarily by boys and imagining myself with them. I still watched the occasional straight porn, but no… Read more

.......after that first afternoon, everything changed. I would play dress up any chance I got. I kept my body shaved and grew my hair a bit longer so I could part my bangs and hold the rest of my hair back with a flowery, sparkly harband. Sooo cute. I experimented with makeup styles: subtle eyeshadow with shiny pink gloss to thick eyeliner with dark red lipstick, always with lengthening mascara. By the end of a month I had modeled all her panties, bras, stockings, tights, swimsuits, ballet and dance costumes, dresses. I think I looked cutest in a tight, low cut, yellow sundress with pink fl… Read more

when i was in jr high and hs i used to get turned on and masturbate to girls in tights, frilly dresses, pinks, purples and fantasized about having sex with them. pretty typical boy. my life changed when i decided to see how i looked as a girl. my older s*s was my size and i snuck into her room while she was away one afternoon. as soon as i opened the panty drawer, my cock got hard and i was hornier than i had ever been. i sorted through all of the panties: boy shorts, lacy thongs, pink, light blue lacy, tight black hip huggers and chose a lacy pink thong to try on. i slid it over my legs a… Read more

Don't think this can't happen to you. Because it happened to me. I kept daring Sara to turn me gay. I used to be so ultra macho and loved women and pussy so much, I didn't think it would ever happen to me. But it did. Beware. First, Sara made me watch gay porn and stop watching pussy porn. OK so I was jerking to cocks, but I still loved pussy after jerking to gay porn for a few weeks. I taunted Sara and told her that she had no power over me. She told me that I would just need a little more time for my training and new sexual destiny to take hold. She told me to buy a butt plug and a Je… Read more

Listen up you white whore, and listen good. I know you want BLACK dick: big, hard, thick black dick. You know that sorry excuse of a clit you have can’t satisfy anyone, it’s not hard enough, big enough, you know you don’t have the skills to stroke and pump a real pussy to pleasure. You’re a white faggot. You want hard black cock ramming your slutty asspussy, fucking your throat, shoved up your tight asshole until it pumps thick, hot, virile sperm in your white boi cunt. You want to be used, I’m going to make sure you are used you until you can’t take it anymore, until your body is no… Read more

my wifes been on an oredering spree lately. the latest order she made had a collar and a strapon. the collar is big and red something that really stands out, and the strapon is 12 inches long and about 1&1/2 inches wide. she actually got a rambone which is 15inches long and 2 inches wide, but i couldn't handle it so she got one a little smaller to get me streched open. the biggest she ever used on me was 8 inches long and 1 inch wide. so last night she told me to get the new dick ready cause it was time. i jumped up and put the new dildo in the ha… Read more

The other day I met a black man on the street and he took me back to his place. As soon as the door was closed I stripped down completely naked. He asked me to give a little turn so He could see the whole package. I gave a slow little spin then bent over to show him my “boy pussy” (as he called it). He dropped his pants and kicked them to the side revealing his 10” swinging member. He sat down in a big chair and told me to get on my hands and knees and crawl to him to service his cock. I dropped to all fours and slowly crawled over to his dangling cock. I gave it a little sniff and the into… Read more

Last Friday night I ventured up to Salisbury MA to spend some fun time at the Leather & Lace adult bookstore. I have been there before en femme and in drab. Never really disappointed. I got into my booth--gloryholes to either side. Immediately sucked on a nice 8 inches with a large cock head. He came twice in my mouth. Yum!!! Then a couple came into the booth on the other side. The girl sucked and stroked me and ran her hands up my stockinged legs--ooh that felt good. And she let me suck her BF off twice--he had a very nice cock--so soft and smooth. I sucked a few other guys off and… Read more

My friend Jamal sent me a message that he had got me a long blue wig off of eBay. He told me to bring a pack of 24" zip ties and come to see him. When i got there, he demanded my keys, ID, money and cell phone. He likes me to be totally dependent on him while i'm there (he gives them back when he's through). He took me into a video booth in the back of the ABS that he runs. Once in the booth i had to put on the wig, strip to panties and surrender my clothes. He made me kneel in the booth in my purple panties and blue wig. My ankles were crossed and ziptied so i couldn't get up. Wrists were cro… Read more

i once served a black Master named Jamal, He demanded some changes in the way that i dressed. First He required me to dispose of all of my male underwear and wear a camisole and either red, pink or purple panties. He told me that when i was at home, i was to wear female clothes since i'm a sissy. One Saturday morning, i painted my toenails a bright red, then was cleaning the house in a blouse and capri length pants when there was a knock on the door. Two young black men that i recognized from Jamal's house were there. "Jamal wants you." "Let me get dressed." One grabbed my arm and led me to… Read more

It was around midday i was bored and feeling a little naughty so decidied to put some underwear on which consisted of stockings suspender belt thong and a bra all in black and all matching. Once dressed i decided to pop out into the garden for a smoke so i put a dress on just to cover up a little and out i went and instantly my cock began to grow in my panties so i started to have a rub through the dress while leaning against the wall. I thought i heard a noise but then thought i couldnt of so carried on rubbing away then i heard someone say I thought i had seen someone in womans clothes i… Read more

I just woke up and I had the hottest dream and it was about you! lol I guess you were still on my mind after drooling and dripping over your new school uniform photos lol. We were in a hotel room. You were wearing a hot black latex outfit, matching thigh high boots, and a latex mask. You had me bound, blind folded and naked on a chair. You were repeatedly slapping me across my face, pulling my hair, spitting in my mouth and calling me derogatory names. You then placed a ball gag in my mouth then afterwards you placed nipple clamps on both of my nipples and placed individual clamps on… Read more