Confessions tagged with 'crossdresser'.




March, 31, 1995,

I was babysitting at our neighbour’s house; as soon as she was out I stripped down to my lingerie for some fun,

I wore a black and red lacy suspender belt with black fishnet stockings and some plain black high heeled shoes, I didn’t have any panties so I went to her bedroom and took some of hers, I put them on and went back downstairs where I put on a porn film.

I really got into my night and forgot to watch the time, I was fucking the hell out of my now really abused and stretched arse with a wine bottle as I watched a woman take a horse cock in her mouth, I thought to myself “I’ll do that one day” just then l heard a noise in the kitchen, I passed it off as her dog wanting to go out and ignored it.

As I sank as far down the bottle as I could get the kitchen door opened and my neighbour walked in she stopped dead in her tracks and asked what I was doing,

I replied “rather obvious really” she sat down and said “carry on then” I slowly slid my arse up and down the wine bottle as she said “Jesus I won’t even take a finger in my bum!” I just carried for a while until her dog whined so I stopped to go and take it out.

As I was getting off the bottle she noticed I was wearing a pair of her panties,

“YOU CAN GET THEM OFF YOU DIRTY FUCKIN PERV” I took them off and gave them to her then I took out her dog.

When I went back in she was watching a woman with a dogs cock in her ass, my neighbour asked if I would ever let a dog fuck my ass!

I said “given the chance” she smiled and called her dog into the room “there you go”

I dropped to my knees and stroked at its cock until it started to show then I took it into my mouth sucking and slobbering away I was in heaven, the dog soon started trying to hump at my face so I moved it around behind me after a couple of sniffs and a lick he mounted me and went berserk trying to force himself as deep into me as he could get.

When he could get no deeper I felt his knot swelling inside my ass, he made a move and got himself turned so we were ass to ass!

I had been knotted before but not by such a large dog, I could feel every spurt off his spunk entering me and could even see his cock making a bulge in my lower stomach.

After what seemed like ages he stopped cumming and started to go limp which meant I would soon be free, as he slid out of my ass I span around and took him deep into my mouth and licked and sucked him clean.

I still had an ass full of spunk and a wide gaping hole to deal with, as I was wondering what to do I felt my ass being stretched again as I turned I saw my neighbour pushing the wine bottle back into my ass.

“stop that mess leaking onto my carpet” I was then pushed out into the back garden where she pulled the bottle out of my ass and giggled as there was a loud splat off dog spunk hitting the floor between my feet.

We went back in and I licked the splash’s of spunk off my shoes before getting changed back into my clothes and taking my film out of the player and going home where I sucked and fucked my bull terrier.

The next day while she was still very hung over she saw me taking my kids to school and asked what had happened the night before as she had knickers full of spunk and a wine bottle covered in lube in her living room,

I told her she had brought somebody home and that I heard him leave about 1am,

She said “oh ok then I just thought it had something to do with you” I told her I had drunk the wine but that was all and she left it at that.

Never did get asked to babysit again though!




I am finally ready to put down in words what I did on my tenth wedding anniversary, I Always got on with my in laws and they had been with me on my stag night.

So now ten years later my wife's idea to celebrate was to redo our stag and hen nights, now fast forward to the night and we are having our "Tarts and Tramps" night where all the men dressed as Tarts and the girls as Tramps (sluts and bums in the usa) but on the night only two guys including me turned up as Tarts,

after a few drinks and a couple of hours we were quite tipsy and found ourselfs in a gaybar! it wasn't long before I was in the toilets sucking cock through a gloryhole, now this is where the night got interesting as I exited the cubicle i was face to face with my entire group who had all had a blowjob from me including my father in law.

we went back to the hotel and i spent the rest of the night being used by my stag party.

i was still being used when my Mother in law, Wife And her friends walked in to "surprise us" well the surprise was on them as i had my father in law Balls deep in my ass and my two brothers in law taking turns fucking my face and i was covered in spunk.

To my surpris they just closed the door and watched until there wasnt a stiff cock left for me to use then they went back to their hotel room and slept.

On several nights since my wife has invited her family to use me while she and her mother watch.

My wife now wants to see me service an entire Rugby team or two! but she never does anything except watch which i find strange to say the least.




I'm a crossdresser. My wife and I have a very open marriage and she supports me in this. We are about the same size and I let her have all the cock she wants and she lets me have all the cock I want as well. A couple months ago we got me all dressed up. She was impressed that I looked as good as she did. She kissed me and told me to have fun. I had sucked a couple of cocks before but had never been fucked. I tot to the gay bar in town and sat at the bar. After a couple of beers a good looking guy sat next to me and offered to buy me a drink. I told him right away I was a man looking for some cock. He didn't seem to mind and kept buying me drinks. After about four I was reeling. He offered to show me a good time so I agreed to let him take me to his place. He drove.

It was a trailer park and I was a little disappointed but knew I wanted a cock that night. We walked in and he locked the door. It was actually quite nice inside. He said he was in town for a year for his job and his wife was in another state. Then he said he really liked fucking little pussy boys like me. I was offended at first but then thought this might be fun. Then he said to get down and suck his cock. I was more than eager and when I unzipped his pants and pulled his cock out I was impressed. It was much bigger than mine and uncut. I put him in my mouth and rolled his foreskin over the head and he was soon hard. He had me suck on his nuts and keep him hard with my mouth. I have naturally long hair and he twirled his fingers in the back and pulled me onto his cock until I was starting to choke. Then he called me a little man-cunt and said he was going to fill my throat. With him pulling my hair toward him I didn't have much of a choice when he started cumming. I swallowed every drop and even sucked him clean. He stayed hard and said to strip while I sucked him. I had been on hormones and my tits were fairly small for a woman but pretty big for a man but my nipples were quite large. When I got my top and bra off he pinched both nipples and pulled until I begged him to stop. He said "I'm gonna make you cry cunt." He pulled and twisted until I actually started to cry a little. It hurt but at the same time my cock was growing. It's not big but still gets pretty hard. When I asked if he was gonna suck my cock he said "No. I don't suck cock. I only fuck little fags like you."

He told me to turn around and get on all fours. I was grateful he stopped mashing my nips so I turned around and knelt on all fours. He rubbed my asshole for a few seconds with a wet finger then shoved his large cock into me. It about split me in two. He wasn't slow or easy but started to fuck me hard and deep. I was openly weeping as he fucked me for the next 15 minutes. By about minute five my asshole was numb and within a couple more minutes I was pushing back as he thrust in. Man this guy could fuck. I told him I had never been fucked in the ass before and he said that after this I wouldn't want anything smaller than his monster cock. He finally came again and filled my ass. Then he pulled his cock out of my ass and had me suck him again until he was ready to cum a third time. I took it all once again and he finally pulled out after I had cleaned him off completely.

When he was completely spent and clean he pulled out of my mouth and said it was time for me to get the fuck out. He wouldn't even drive me back to my car. It was about two miles away and I finally staggered to my car. When I got home my wife needed to hear all about it. When I told her I finally got ass fucked she almost leaped with joy. Then she pulled out a strap on that I didn't know she had and told me to get on all fours. I stripped and knelt on the bed where she proceeded to fuck me for another half hour and I actually came on the bed with her rubber cock in my ass. It was the start of something awesome and now she fucks me at least four times a week. My tits are growing and my cock is shrinking and we have decided that not only am I her bitch but her whore as well.




I'm married but by wife is a little frigid so I go to the gay bars to try to get my cock sucked. I was horny last Friday night but she wasn't in the mood so I told her I was going to get my cock sucked. She was aware I sometimes get a little strange and she seems to be okay with it. I went to the bar and happen to meet Johnny. He was a crossdresser and his lips looked like they could suck for hours. When I mentioned that he said I was right. He said he had a van outside and we could go to his van and have fun in the back. His van had no back seats, only a mattress and when he closed the door he said I was about to have the best blowjob I'd ever had. He took my pants and shorts off and knelt down. He took my cock into his mouth and sucked me hard. He took my entire six inches into his mouth and when I started cumming he didn't even flinch, but instead swallowed every fucking drop. Then he took off his pants and told me to suck his cock. I laid down and he hovered over me and stuck his cock in my mouth. I sucked him until he was hard. Then I told him I wanted to be fucked. He said he was a bottom but he would make an exception. I lifted my legs and he scooted up to me. His cock got hard again after he stroked it a few times. He wet a finger and started to finger fuck me. It felt really good and when I said I needed him in me he took his finger out of my asshole and put his cock up to my asshole. He pushed in and started to fuck me. It felt so fucking good I didn't want him to stop. I kept telling him to fuck me deeper and his nearly seven inch cock reached to the bottom of my bowels. He fucked me for the next 10 minutes and then came in my ass. I felt it ooze past his cock down my ass and felt totally satisfied. Then he pulled his cock out of my ass and spun me around. He put his cock back up to my lips and had me finish him off.. Then he sucked me hard again and sat on my cock. He bounced up and down until I war ready to cum. He said to give it to him and I came in his ass. We ended up making out for about 15 minutes and he sucked my cock again until I filled his mouth with my cum. Then he got off of me and told me I had to leave.

When I got home my asked how it went. When I told her I found a C/D that sucked my cock and fucked me she didn't believe me. She acted nonchalant and just went to bed. I took a shower and hopped into bed. It was one of the best night sleeps I'd ever had.




I had never been sucked off or fucked by a tranny before.

I answered a C/L ad for a TV looking for a man. I figured he was just a crossdresser, a man in drag, so when I actually met him I was surprised. I went over to his place, and he answered the door in a skirt and blouse. We chatted for a minute, then we sat on the sofa. I leaned over and kissed him. He had very soft lips, and when his tongue parted my lips I responded. My dick was already getting hard.

He said, "Let me show you." He took off his blouse and bra, and there were the nicest pair of perfectly formed tits I had ever seen. His nipples were large, with large aeroleas to match. He said they were natural, that he was born that way. I massaged and caressed them, running my fingers around his nipples and finally tweaking and pulling on them.

I leaned down and started to suck a nipple, and he said, "Oh, honey, that's so good. You're making my cock hard." With that I snaked a hand under his skirt to find a very large, thick cock. My cock is about five inches hard, so his seven inches made me feel inadequate. I have to admit my own dick was getting hard. "Suck me, honey," he said. I bent down and took his cock in my mouth. He got rock hard almost immediately.

I've always enjoyed sucking on a nice cock, but never while playing with tits the size of his. He had me lay down on my back with my head hanging off the arm of the couch. He stood up and walked over to my head and put his cock back in my mouth. I played with his nuts, then around to his ass. "You ever been fucked?" he asked. "No, just oral." "Then you're in for a treat," he said. He had me kneel on the floor with my chest on the couch. He knelt behind me and started to lick my asshole. I had never been rimmed before, either. I felt like a fucking amateur. He started to tongue fuck my ass. It felt great. He had my asshole nice and slippery, then got up behind me and put his cock up to my asshole.

I wasn't really too sure about this, especially when he shoved his cock in. I felt the 'pop' when he pushed past my pucker spot. It hurt, but I tried to relax. He held it there for a couple of minutes until the pain subsided. I told him it felt good, and he started fucking me in earnest. Each time he thrust in I felt my own cock twitch. He fucked me for about 10 minutes, then pulled out.

He had me lay down on the carpet on my back. "I want to see your face when I cum in your ass," he said. He pushed my legs up and put his cock back in my ass. I moaned. "Oh, yeah, fuck me," I told him. His eyes never left mine the entire time he was fucking me. He started to stroke my cock in unison to his fucking. He told me to pull on his nipples, so I reached up and took a nipple in each hand. I pulled a bit, and he told me to pull harder. I tugged on his nipples until they stretched no more. He fucked me harder and faster until I felt him tense up and say, "Oh, fuck, I'm gonna cum." I pulled his nipples as hard as I could and he started cumming. "Oh, fuck, fuck, fuck," he kept saying as he filled me with his jiz. When he was spent he pulled his cock out of my ass and knelt down between my legs and started to suck me. He shoved two fingers up my ass as he sucked me. He was finger fucking me while blowing me. I lost control and started moaning. I didn't give any warning, but just started to cum. He clamped his lips around my cock so no cum would escape and took my entire load.

He sucked me until I was totally clean. He then laid down next to me, and for the next 20 minutes we kissed and explored each other's bodies. I finally had to leave, as my wife thought I just went out for cigarettes.

This was a great experience for me, and I look forward to many other nights with Terri.




I am sitting here with a school girl skirt,panties and bra. I am 52 man and I so much want to ram my old cock down the throat of a naked underage girl who is on her knees before me. I cum over her hot pretty face and in her soft young mouth, the cum is never gunna stop as buckets of man juice spirt like a cannon over her begging pretty soft face. Fuck, what a massive wank fantasy that all men go through. Hey wives, that what we thinking about when we trying to touch the sides of your old stinky stretched pussy. Fucking the wife is just one step up from masturbation.Fucking a 16 year old tight pussy and suckling on her young small soft but firm tits. Only thing that makes us cum. Wearing school girl dresses and skirts is a turn on for men cuz its the closest we gunna get. Good when the girls name is in the skirt cuz its the name to yell out when cumming all over her skirt.Watching the little sluts walking to the bus stop in their short skirts knowing men are driving past fantasizing about them is what they love. Watching them sit down and knowing there skirt is getting higher to show more perfect soft young leg is also there turn on. Theb stupid sluts give a man a dirty look but they loving every minute cuz they know exactly that we thinking about ramming those legs apart and banging their little tight sweet smelling cunts. Yummy Cunt Honey is what it is. Makes those tight sweet smelling underage pussies of paradise all wet and tingling. Wear a condom, get those old man cocks out and wank like mad when driving past. At least its being able to cum whilst actually being close to an underage school girl. I got access to a mega hot 13 year old girl soon, wont touch her or nothing but mite put a camera in the shower and toilet.I will get her sweet used panties with her cock hardening cunt honey scent and put them on my face and sniff and jerk till I shoot a massive load. Done it before with her panties. Would actually like to try having a sweet boys young cock in my mouth, have him shoot his young sweet load down my throat. Yum.