First Time Shemale Sex.

[smm5437]

Hey guys, I'm new here so I thought I would give this a shot.

This thread is simple, if you ever had sex with a shemale, post your story of your first time here.

 

[smm5437]

I'll start.

About a month ago, I was talking to this shemale online and she gave me her phone number so we could set something up. I called her that night and set up a rendezvous for the next morning. I couldn't even sleep that night, I was so excited. I have had the fantasy of shemale sex for a longtime and I couldn't wait for the next morning. I went a couple towns over and met her at her apartment. Her roommate was gone for the day, so it was just me and her. She greeted me with a hug and a kiss. We did not waste anytime and headed up to her bedroom. I could still smell the sweet aroma of her shampoo as she was walking up the stairs.

As soon as we got up there she told me to take my pants off and she took her skirt and top off. I immediately noticed her uncut dick and I got instantly hard. Finally, I could live out this wonderful fantasy of mine. We started getting sensual and touchy-feely, and she got hard. She was about 6 inches, perfect size for a newbie like myself. We started fondling each others cocks and it got really steamy. I immediately went right for her cock with my lips and started sucking with no hesitation for my first time. It was like I was in Shemale cock heaven. I loved the feel of her dick sliding in and out of my mouth. She kept telling me to slow down because I was going to make her cum. She then made me stop and started sucking mine. She was PHENOMENAL at giving head. I was starting to lose it and finally stopped her. I asked her if she had lube and I can tell she was waiting for me to ask that.

When she got back with the lube, I had the condom on and ready to go. She quickly helped me lube up her asshole. I began fucking it for a good 7 minutes. We then stopped and I wanted to take her inside my ass. I plopped on my back and threw my legs up in the air. She began to finger my anus. It hurt a little and then she took it upon herself to put her stiff cock in me. We tried for about 5 minutes to fit it in, it wasn't going. She then just took my cock in her mouth for another 10 minutes and I blew a huge load all over her chest. I then masturbated her while I liked my cum off her chest. She blew a huge all over my hand and her stomach. I took the liberty of feeding her her own semen. It was quite possibly the hottest thing I have ever seen. I then picked up my clothes changed and left. She gave me a nice kiss on the way out.

I enjoyed it soooooo much and it was everything I thought it was going to be. Possibly the greatest sexual experience I will ever have. Not many people get the chance to have an experience with a shemale. I can honestly say I experienced it at the young age of 20.

 

[afstud]

wow that was a hot story.....i have been dreaming of being with a shemale but have not have the pleasure as of yet though

 

[smm5437]

If you get the chance, do not turn it down. It is everything you could ever want in a sex partner.

 

[eyeball1]

Any thoughts on the do's and dont's of a first time experience with a transexual woman? I have a good potential myself and am a bit nervous about it. I've thought about it for years but was unable to make it happen. Lots of sex with genetic women but never anything like this and only had anal sex a few times with a g.w. . She's very femme and completely into being the bottom, which is fine by me.

 

[albertaboy]

Great story, a fantasy of mine.

 

[levidebacker]

i used to date a female to male tranny. he had a huge clit and we had lots of fun.

 

[smm5437]

Any thoughts on the do's and dont's of a first time experience with a transexual woman? I have a good potential myself and am a bit nervous about it. I've thought about it for years but was unable to make it happen. Lots of sex with genetic women but never anything like this and only had anal sex a few times with a g.w. . She's very femme and completely into being the bottom, which is fine by me.

If you had anal a couple times before you shouldn't have a problem. That was the only problem I had, she couldn't fit it in haha. I still had a great time though. You should definitely go for it. Even if you don't like it, you at least tried it. Go have some fun! Then be sure to post here about it. I am looking forward to hearing about it.

 

[Wolf of Mibu 69]

One thing you'll find is useful to note is that 'shemale' is not the preferred nomenclature. It's a term coined by the porno industry, and many of the transgender community find it offensive.

With that said, pre-op mtf transsexuals are extremely intriguing to me, and I fantasize about them often.

 

[temp256]

I've had one experience. She seduced me, then later said it didn't mean anything. We're still friends, but I've felt cold towards her ever since...

 

[hbgsteelersfan]

Hey guys, I'm new here so I thought I would give this a shot.

This thread is simple, if you ever had sex with a shemale, post your story of your first time here.

I've been trying to set something up with a trans from my home town here but it hasn't worked out. Sounds so hot and very intriguing.

 

[longnmguy]

Couple of times

first was in san francisco. extremely hot (look up susan shah)...we sucked and fucked for a couple of hours. one of the most erotic experiences i've ever had. she seemed genuinely turned on by me, which made it even hotter.

2nd was post-op friend near here. Incredible lover...she was so sweet and kind.

never, ever, pass up the chance...

 

[Lv_2_be_pegged]

would love to try

I would love to go out with pre-op Tgirl, I have just never ecountered one. I passed by one (I think) in the airport going the opposite direction, but that's it. How do you find these women?

 

[mannishboy]

My first transexual experience was...simply amazing. She was a pacific islander, Samoan I think, with a smokin slim body that I met out of town. She put on a leather and chain teddy while I lay on the bed, then straddled me. She moved up to place her cock in to my mouth and I sucked like my life depended on it! It felt incredible feeling her get hard in my mouth. She was about 8 inches or so and I'll never forget how turned I was seeing it. I moved down to her balls and she moaned enough for me to continue down further to her ass. When I licked her sweet hole (it was so smooth) she started grinding her ass into my face and moaning loudly. So after I spent a while there I moved back and and she face fucked me for a while - she got a bit carried away at one point and I gagged a little, but I seemed to do ok for a first timer. Eventually it was time and while I was still on my back, she lubed me and then lifted my legs up so my feet were over her shoulder and entered me. It hurt, no doubt about it, but it wasn't as bad as I thought - kind of a dull pain deep inside, but it was well worth it. She pounded me for what seemed like an eternity and when she began picking up pace and moaning I told her I wanted to see her come. Sure enough she pulled out, moved back up to my face while jerking furiously and to my surprise pushed herself back into my mouth and face fucked me again for a bit. I never thought about ass to mouth and would never thought I would agree to it, but damn it was all way to hot and fast to refuse! Soon she needed to blow so she pulled her cock out of my mouth and jerked a load onto my face. I'll never forget it and the memory has fueled many a lonely night of self lovin.

 

[albertaboy]

My first transexual experience was...simply amazing. She was a pacific islander, Samoan I think, with a smokin slim body that I met out of town. She put on a leather and chain teddy while I lay on the bed, then straddled me. She moved up to place her cock in to my mouth and I sucked like my life depended on it! It felt incredible feeling her get hard in my mouth. She was about 8 inches or so and I'll never forget how turned I was seeing it. I moved down to her balls and she moaned enough for me to continue down further to her ass. When I licked her sweet hole (it was so smooth) she started grinding her ass into my face and moaning loudly. So after I spent a while there I moved back and and she face fucked me for a while - she got a bit carried away at one point and I gagged a little, but I seemed to do ok for a first timer. Eventually it was time and while I was still on my back, she lubed me and then lifted my legs up so my feet were over her shoulder and entered me. It hurt, no doubt about it, but it wasn't as bad as I thought - kind of a dull pain deep inside, but it was well worth it. She pounded me for what seemed like an eternity and when she began picking up pace and moaning I told her I wanted to see her come. Sure enough she pulled out, moved back up to my face while jerking furiously and to my surprise pushed herself back into my mouth and face fucked me again for a bit. I never thought about ass to mouth and would never thought I would agree to it, but damn it was all way to hot and fast to refuse! Soon she needed to blow so she pulled her cock out of my mouth and jerked a load onto my face. I'll never forget it and the memory has fueled many a lonely night of self lovin.

Hot, great fantasy of mine...except the ass to mouth.

 

[mannishboy]

Hot, great fantasy of mine...except the ass to mouth.

Yeah, it's not something I wanted or would do again - it just goes to show what a person is capable of in the heat of the moment!

 

[Lv_2_be_pegged]

My first transexual experience was...simply amazing. She was a pacific islander, Samoan I think, with a smokin slim body that I met out of town. She put on a leather and chain teddy while I lay on the bed, then straddled me. She moved up to place her cock in to my mouth and I sucked like my life depended on it! It felt incredible feeling her get hard in my mouth. She was about 8 inches or so and I'll never forget how turned I was seeing it. I moved down to her balls and she moaned enough for me to continue down further to her ass. When I licked her sweet hole (it was so smooth) she started grinding her ass into my face and moaning loudly. So after I spent a while there I moved back and and she face fucked me for a while - she got a bit carried away at one point and I gagged a little, but I seemed to do ok for a first timer. Eventually it was time and while I was still on my back, she lubed me and then lifted my legs up so my feet were over her shoulder and entered me. It hurt, no doubt about it, but it wasn't as bad as I thought - kind of a dull pain deep inside, but it was well worth it. She pounded me for what seemed like an eternity and when she began picking up pace and moaning I told her I wanted to see her come. Sure enough she pulled out, moved back up to my face while jerking furiously and to my surprise pushed herself back into my mouth and face fucked me again for a bit. I never thought about ass to mouth and would never thought I would agree to it, but damn it was all way to hot and fast to refuse! Soon she needed to blow so she pulled her cock out of my mouth and jerked a load onto my face. I'll never forget it and the memory has fueled many a lonely night of self lovin.

Wow!! Really hot! You are lucky as hell!

 

[fishmiester]

I'll start.

About a month ago, I was talking to this shemale online and she gave me her phone number so we could set something up. I called her that night and set up a rendezvous for the next morning. I couldn't even sleep that night, I was so excited. I have had the fantasy of shemale sex for a longtime and I couldn't wait for the next morning. I went a couple towns over and met her at her apartment. Her roommate was gone for the day, so it was just me and her. She greeted me with a hug and a kiss. We did not waste anytime and headed up to her bedroom. I could still smell the sweet aroma of her shampoo as she was walking up the stairs.

As soon as we got up there she told me to take my pants off and she took her skirt and top off. I immediately noticed her uncut dick and I got instantly hard. Finally, I could live out this wonderful fantasy of mine. We started getting sensual and touchy-feely, and she got hard. She was about 6 inches, perfect size for a newbie like myself. We started fondling each others cocks and it got really steamy. I immediately went right for her cock with my lips and started sucking with no hesitation for my first time. It was like I was in Shemale cock heaven. I loved the feel of her dick sliding in and out of my mouth. She kept telling me to slow down because I was going to make her cum. She then made me stop and started sucking mine. She was PHENOMENAL at giving head. I was starting to lose it and finally stopped her. I asked her if she had lube and I can tell she was waiting for me to ask that.

When she got back with the lube, I had the condom on and ready to go. She quickly helped me lube up her asshole. I began fucking it for a good 7 minutes. We then stopped and I wanted to take her inside my ass. I plopped on my back and threw my legs up in the air. She began to finger my anus. It hurt a little and then she took it upon herself to put her stiff cock in me. We tried for about 5 minutes to fit it in, it wasn't going. She then just took my cock in her mouth for another 10 minutes and I blew a huge load all over her chest. I then masturbated her while I liked my cum off her chest. She blew a huge all over my hand and her stomach. I took the liberty of feeding her her own semen. It was quite possibly the hottest thing I have ever seen. I then picked up my clothes changed and left. She gave me a nice kiss on the way out.

I enjoyed it soooooo much and it was everything I thought it was going to be. Possibly the greatest sexual experience I will ever have. Not many people get the chance to have an experience with a shemale. I can honestly say I experienced it at the young age of 20.

What a hot read. I am looking forward to my first. I like the "pre-view" so to speak. My cock is just dripping with pre-cum...yum. I will for sure post it when it happens. Thank you os much for sharing....very hot..

 

[statutoryape]

......

 

[eyeball1]

Eh, she got sketchy and stopped communicating with me. I didn't bother to pursue it farther. Chasing genetic women is enough trouble right now.

 

[lovebothsexes]

hot story

I'll start.

About a month ago, I was talking to this shemale online and she gave me her phone number so we could set something up. I called her that night and set up a rendezvous for the next morning. I couldn't even sleep that night, I was so excited. I have had the fantasy of shemale sex for a longtime and I couldn't wait for the next morning. I went a couple towns over and met her at her apartment. Her roommate was gone for the day, so it was just me and her. She greeted me with a hug and a kiss. We did not waste anytime and headed up to her bedroom. I could still smell the sweet aroma of her shampoo as she was walking up the stairs.

As soon as we got up there she told me to take my pants off and she took her skirt and top off. I immediately noticed her uncut dick and I got instantly hard. Finally, I could live out this wonderful fantasy of mine. We started getting sensual and touchy-feely, and she got hard. She was about 6 inches, perfect size for a newbie like myself. We started fondling each others cocks and it got really steamy. I immediately went right for her cock with my lips and started sucking with no hesitation for my first time. It was like I was in Shemale cock heaven. I loved the feel of her dick sliding in and out of my mouth. She kept telling me to slow down because I was going to make her cum. She then made me stop and started sucking mine. She was PHENOMENAL at giving head. I was starting to lose it and finally stopped her. I asked her if she had lube and I can tell she was waiting for me to ask that.

When she got back with the lube, I had the condom on and ready to go. She quickly helped me lube up her asshole. I began fucking it for a good 7 minutes. We then stopped and I wanted to take her inside my ass. I plopped on my back and threw my legs up in the air. She began to finger my anus. It hurt a little and then she took it upon herself to put her stiff cock in me. We tried for about 5 minutes to fit it in, it wasn't going. She then just took my cock in her mouth for another 10 minutes and I blew a huge load all over her chest. I then masturbated her while I liked my cum off her chest. She blew a huge all over my hand and her stomach. I took the liberty of feeding her her own semen. It was quite possibly the hottest thing I have ever seen. I then picked up my clothes changed and left. She gave me a nice kiss on the way out.

I enjoyed it soooooo much and it was everything I thought it was going to be. Possibly the greatest sexual experience I will ever have. Not many people get the chance to have an experience with a shemale. I can honestly say I experienced it at the young age of 20.

very arousing am 65 and never have I been with a shemale would love to give it a try but have diabetes and therefore have ed so it will probably never happen (sigh)

 

[BiDrew42]

My first experience with a transsexual occurred when I was 22. I was visiting my favorite adult bookstore and happened on a swingers magazine called "Unique Encounters." I wasn't really looking for a TS but there were numerous ads, most with pictures, of TS's seeking "generous" men for adult fun. It took me awhile to build up the courage to make an appointment but I finally did.

I went to her apartment, which was actually only a few blocks up the beach from mine. Her name was Dusty, and when she opened the door I thought she was gorgeous. I also wondered how it was possible that the very sexy woman standing before me could really be a man. Dusty had long, curly blond hair (not a wig), sexy, feminine features, and had large breasts with lots of cleavage showing. She was wearing tight white jeans, a gold top made of some type of metal-like material that covered only her front (there was a strap around her neck and one around the back, and 4" stillettos. She had a beautiful smile and I was instantly aroused.

Dusty led me to the bedroom and we took care of the finances ($100 per hour) and she asked what I was interested in. When I explained what I wanted she asked me why I didn't just get a man. I told her I had been with plenty of men but wanted to try sex with a TS. She then told me that if I really wanted to have sex with a TS that I should just treat her like a lady. I really didn't understand what she meant but I agreed to let her take the lead and show me.

Dusty kissed me on the lips, and then she began stripping me while we made out. When I was naked, she squatted down in front of me and took my rock hard cock into her hand and then began lickig it all over, starting at the base of my shaft and working up to the head, running her tongue over every inch. After several minutes of that she took my cock into her mouth and proceeded to give me a fantastic blow job. She used her hands to stroke my shaft and fondle my balls as well. When I thought I was going to explode she stopped and smiled up at me. Then she stood and kissed me again.

Dusty pulled away and turned around, asking me to untie her top. I did while admiring her butt, and when I had the straps untied she turned around and removed her top. She had very nice breasts and her nipples were hard. I leaned forward and kissed her left nipple, and she wrapped her hands around my head and pulled me closer. I spent several minutes kissing, licking, and sucking her breasts and nipples, and she was moaning with pleasure. Then she pulled away and removed her jeans and heels while I watched. She was wearing a very sexy pair of black panties.

Dusty stepped close to me and removed her panties. As she slid the panties down her neatly trimmed pubic hair came into view and finally I could see her cock, which she had tucked up between her legs. After completely removing her panties she stood in front of me and pulled her cock fully out so that it dangled just a few inches in front of my face. It was bigger than mine! Uncircumsized, long and thick, and only semi-erect at that point, I wanted nothing more than to have it in my mouth. I reached out for it but Dusty pushed me back onto the bed and knelt in front of me, taking my cock into her mouth instead.

After several more minutes of incredible oral sex, Dusty looked up and asked if I was ready to eat her pussy. I said that I was and we changed positions. She laid on her back and spread her legs and I laid down between them, ready to give her the best blow job of her life. She had her hands cupped over her cock and balls however, and told me before I could taste her clit I had to eat her pussy. She lifted her legs and exposed her ass to me and I finally figured out what she wanted. I leaned forward and ran my tongue up and down the crack of her ass several times, then spread her wide and began rimming her. She was moaning with pleasure and her "clit" had become fully erect. I still wanted to suck it but I was enjoying her reaction to what I was doing so much that I just kept doing it.

Dusty finally told me to suck on her clit and I withdrew my tongue from her ass and buried my face in her cock and balls. She was dripping pre-cum so I licked the tip of her cock. I was a pretty experienced cocksucker at that point and I gave her my best. She came in my mouth several minutes later and I drank her dry. I licked her clean and then she asked me to fuck her pussy.

I was ready and she handed me a tube of Astroglide and I quickly lubed up my cock and her pussy. She remained on her back and I entered her that way, plunging deep inside her and then remaining very still while she relaxed. My cock was throbbing and she could feel it. She looked me in the eyes and I began fucking her, slowly at first but building up to a steady rhythm quickly. She kept eye contact the entire time I fucked her. I lasted a lot longer than I thought I would, but emptied myself into her about 5 minutes after I started. When I pulled out I noticed that she was very drippy again so I lowered my head and cleaned her pre-cum off her belly and cock.

I was surprised that my hour was up and asked if I could stay longer. She told me she had another customer coming and I would have to come back another time. We cleaned up and I dressed and she escorted me to the door. She gave me a long passionate kiss at the door and I left. I saw her several times after that and we spent a memorable weekend together as a couple in the Bahamas. That cost me a lot of money but was well worth it. I was also seeing other TS's that had advertised in my trusty copy of Unique Encounters.

 

[Pittdude1972]

Nice story Drew. thanks for sharing.

My first experience with a transsexual occurred when I was 22. I was visiting my favorite adult bookstore and happened on a swingers magazine called "Unique Encounters." I wasn't really looking for a TS but there were numerous ads, most with pictures, of TS's seeking "generous" men for adult fun. It took me awhile to build up the courage to make an appointment but I finally did.

I went to her apartment, which was actually only a few blocks up the beach from mine. Her name was Dusty, and when she opened the door I thought she was gorgeous. I also wondered how it was possible that the very sexy woman standing before me could really be a man. Dusty had long, curly blond hair (not a wig), sexy, feminine features, and had large breasts with lots of cleavage showing. She was wearing tight white jeans, a gold top made of some type of metal-like material that covered only her front (there was a strap around her neck and one around the back, and 4" stillettos. She had a beautiful smile and I was instantly aroused.

Dusty led me to the bedroom and we took care of the finances ($100 per hour) and she asked what I was interested in. When I explained what I wanted she asked me why I didn't just get a man. I told her I had been with plenty of men but wanted to try sex with a TS. She then told me that if I really wanted to have sex with a TS that I should just treat her like a lady. I really didn't understand what she meant but I agreed to let her take the lead and show me.

Dusty kissed me on the lips, and then she began stripping me while we made out. When I was naked, she squatted down in front of me and took my rock hard cock into her hand and then began lickig it all over, starting at the base of my shaft and working up to the head, running her tongue over every inch. After several minutes of that she took my cock into her mouth and proceeded to give me a fantastic blow job. She used her hands to stroke my shaft and fondle my balls as well. When I thought I was going to explode she stopped and smiled up at me. Then she stood and kissed me again.

Dusty pulled away and turned around, asking me to untie her top. I did while admiring her butt, and when I had the straps untied she turned around and removed her top. She had very nice breasts and her nipples were hard. I leaned forward and kissed her left nipple, and she wrapped her hands around my head and pulled me closer. I spent several minutes kissing, licking, and sucking her breasts and nipples, and she was moaning with pleasure. Then she pulled away and removed her jeans and heels while I watched. She was wearing a very sexy pair of black panties.

Dusty stepped close to me and removed her panties. As she slid the panties down her neatly trimmed pubic hair came into view and finally I could see her cock, which she had tucked up between her legs. After completely removing her panties she stood in front of me and pulled her cock fully out so that it dangled just a few inches in front of my face. It was bigger than mine! Uncircumsized, long and thick, and only semi-erect at that point, I wanted nothing more than to have it in my mouth. I reached out for it but Dusty pushed me back onto the bed and knelt in front of me, taking my cock into her mouth instead.

After several more minutes of incredible oral sex, Dusty looked up and asked if I was ready to eat her pussy. I said that I was and we changed positions. She laid on her back and spread her legs and I laid down between them, ready to give her the best blow job of her life. She had her hands cupped over her cock and balls however, and told me before I could taste her clit I had to eat her pussy. She lifted her legs and exposed her ass to me and I finally figured out what she wanted. I leaned forward and ran my tongue up and down the crack of her ass several times, then spread her wide and began rimming her. She was moaning with pleasure and her "clit" had become fully erect. I still wanted to suck it but I was enjoying her reaction to what I was doing so much that I just kept doing it.

Dusty finally told me to suck on her clit and I withdrew my tongue from her ass and buried my face in her cock and balls. She was dripping pre-cum so I licked the tip of her cock. I was a pretty experienced cocksucker at that point and I gave her my best. She came in my mouth several minutes later and I drank her dry. I licked her clean and then she asked me to fuck her pussy.

I was ready and she handed me a tube of Astroglide and I quickly lubed up my cock and her pussy. She remained on her back and I entered her that way, plunging deep inside her and then remaining very still while she relaxed. My cock was throbbing and she could feel it. She looked me in the eyes and I began fucking her, slowly at first but building up to a steady rhythm quickly. She kept eye contact the entire time I fucked her. I lasted a lot longer than I thought I would, but emptied myself into her about 5 minutes after I started. When I pulled out I noticed that she was very drippy again so I lowered my head and cleaned her pre-cum off her belly and cock.

I was surprised that my hour was up and asked if I could stay longer. She told me she had another customer coming and I would have to come back another time. We cleaned up and I dressed and she escorted me to the door. She gave me a long passionate kiss at the door and I left. I saw her several times after that and we spent a memorable weekend together as a couple in the Bahamas. That cost me a lot of money but was well worth it. I was also seeing other TS's that had advertised in my trusty copy of Unique Encounters.

 

[smlred1]

I'm in the Club

I'm 56 and have been bicurious for several years. I did experiment when I was about 12, but only letting a younger neighbor boy suck me. Since my divorce I have wanted to taste a cock, but have always chickened out. In the two times I have found a guy to suck me, I have been so nervous that I couldn't get it up.

I have tried to find a couple where the woman would help teach me to suck, but that hasn't worked out because they all want to send me to a pay site. The trans girls in my area who advertise on Craig's List are just plain scary. So, what is a guy supposed to do?

Any understanding t-girls or couples in the Phoenix area/

 

[jakelane]

Honest

I think you are making this story up or at least some of it. Unless I just do not understand. If you have eever eally had any anal sex or played with an anus at all you would know that the whole business of "not getting it to fit" is not a real problem. The anus is very pyable and unless her cock was like more than 4 inches in diameter at the tip it would slide in with no problem. Now the pain you expierience might be a problem but getting it in the hole no question, it will go. But I do like the erotic story and I do love having sex with trannys. If you eer get a chance to go to Thailand take the trip. It is one of the best places in the world and it is full of HOT ladyboys. You are sure to fall in love ther I promise.