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This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.



I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.

I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little selection and those that were in that range were surprisingly stuck up. I was actually really surprised and frustrated. See, not to be arrogant, but I'm a pretty handsome guy. I've got a bit of a belly but I worked out for hours a day to keep it off. I also, to be blunt, have some incredible bedroom skill. I'm almost 8 inches but I rely more on my tongue and hands to please the women, focusing on giving them at least one or two orgasms before I penetrate them. In my hometown, these were all qualities that had me a date every week or so. Women had started passing me around so much that I actually was getting tired of it. I actually had decided just before I moved to stop just having sex with women and find someone serious about dating. See, I'd gotten to the point where I'd give a woman a few orgasms and they'd not even give me one. Sex without feelings just didn't do it for me.

Eventually, after yet another rejection message, I decided to broaden what I was searching for. That's where I met Amy. See, I didn't mention this, but I'd always had a fetish for women with a bit "more" to them. It started off with watching women with strap-ons and moved onto women with the real deal. So, just for kicks, I typed Transexual in the search engine. That's when she popped up. I won't lie, she had one very bad profile pic. However, her profile bio caught my eye, we had a good amount in common, and I decided to send her a message.

I was shocked when she sent one back. I didn't expect it as 3/4's of the women I sent a message to didn't reply back and the rest that did were either rejections or didn't last long. I think I dated two people online, and one honestly just couldn't keep up in bed and the other just lived too far away and was too busy. Anyway, Amy sent me a reply, very friendly and we started talking. We got to know each other really well and actually became good friends for a while. She was semi-new to her MtF transformation and was dealing with a lot of people nearby her that knew her as a guy that gave her grief and I, as a very open-minded man, gave her comfort and support. We wanted to meet each other so badly that we agreed to split the cost and meet each other in a state halfway between us. The deal was that she and I had to actually be a couple, no meeting just for sex.

I was incredibly excited and for the months we had to wait until we could do it (the trip, I mean) seemed like it was crawling by. We did nothing via webcam or online but talk as to keep the sexual tension high, so when the trip did come around I was practically hard all the time (I had to wear jeans and a baggy shirt a lot to try and hide my boner). A flight, skip and a jump away, we were in the same city. We met in the hotel lobby, awkwardly hugging at first, but our chemistry eventually overrode the nervousness and it was like we'd been dating for some time. This woman had become a dear friend to me and I couldn't wait for us to be lovers as well.

We held hands as we checked in, and all the way to our room. Energy flowed between our hands like electricity that tingled all over. I honestly felt so excited that I felt like I was going to start vibrating through things, and she was in a similar mood.

We quickly opened our room and, before the doors even closed, we were on each other like dogs in heat. I had my hands in her beautiful black hair, slowly lowering them to her neck, caressing the back of it gently. She moaned against my lips as my hands moved to her shoulders and then kneaded her lower back. She was like butter in my hands at this point. We went to the bed, our lips never parting, and quickly entangled ourselves together as we passionately kissed for what seemed like moments, but actually turned out to be a few hours.

She pulled her head back and smiled at me. "So this means we're a couple then, huh?"

I smiled and stroked her cheek. "Um, well that was the deal after all." I playfully winked. She rested a hand on my crotch and I shuddered a bit as what felt like electricity came from her fingers.

"I just wanted to make sure," She smiled bigger as she unzipped my pants. I helped her take them off and she began to lightly play with my penis with her hands through my boxers.

"I, um, didn't expect you to be this big," She said a little nervously as my erection grew to it's full extent. I didn't know what to say. Despite my fetishes of strap-ons an the like, I'd never had more than a finger, so I had no idea if bigger was better or worse in this case.

"Is it going to be too painful?" I hesitantly asked. I had no desire to hurt her.

"Well, maybe if I suck it off first we can do more later," She said.

"Yeah, I do admit I'm not normally this hard," I explained. "You're just so beautiful, so sexy, and I've wanted to be with you for so long that I'm really excited."

She blushed a bit and resumed stroking my penis. "Thanks. That really means a lot to me."

I smiled at her, and then quickly gasped as she pulled down my boxers in a quick motion and wrapped those sexy lips around my shaft, then quickly took most of it in.

Like I said before, I'm pretty long, but I'm also pretty thick. Women in the past have told me that while I'm not the longest they've been with, I am definitely one of the (if not the) thickest. No woman has ever been able to deepthroat me, but Amy was the closest I've had. She let my cock sit in her mouth while her magnificent tongue stroked from hilt to tip as best it could, and it felt amazing. She pulled her head back and quickly used her hands to cover the areas her mouth wasn't on. Her head rocked side to side on the tip, sending shockwaves through my body. I actually grabbed the sheets, something I'd never done before like this, in passion, pleasure, and excitement.

"You like that honey?" She said as she began to lick my balls.

"Fuck yes!" I almost yelled. No woman had ever done this to me like this. Actually, of the many women I'd been with, only four ever got me to actually come with a blowjob, and even then I'd had to help out a little. This gal got me so turned on and gave such pleasure that I was fighting not to cum so I could enjoy more of it.

"Cum for me baby," She said so sensually I think my dick got harder. "Cum for me, I want your cum now."

I felt the pleasure build to max. I actually fought hard not to do it, but my penis felt that familiar tightening as it prepared to fire.

"Amy! I'm cumming!" I gasped out, clenching the sheets tighter. She quickly pulled her mouth up and let her hand fly up and down my dick. Then she did something no woman had done for me before, she put her mouth all the way down my shaft and let me explode in her mouth. I filled her up so much that I could feel her heavy swallowing while she struggled to keep all my semen inside her mouth.

"That.... was incredible," I said in a voice just above a whisper. She smiled at me, cum completely swallowed.

"I'm so glad to hear it honey," Her face was flushed but delight emanated from it. "Now lets take a shower and clean up, and perhaps get some dinner before we resume part two."

I've almost never needed a break between my first and second orgasm, which frustrated many of my past girlfriends, so it was no shock to me that I was still hard for her.

"You sure we can't do something else?" I asked, flexing my PC muscle to make my penis twitch and Amy actually looked a bit surprised at how much I could move it.

"I didn't say that we couldn't do something in the shower," She winked as she stood up. It was then that I realized I'd just gotten a blowjob from a transgendered woman, and I'd actually see one naked in a bit. My heart fluttered nervously, but I stood up, still hard as a rock, and followed her into the bathroom.

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Had Amazing Sex with My Crush Who Turned Out to Be a Shemale

My name is Nick. I am Software Engineer residing in Las Vegas- the perfect place to be working by the day and partying by the night. I absolutely loved the night life of Las Vegas. Occasionally on weekends, I went out partying at a nearby nightclub and casino. That is where I met Cassandra. She was a regular visitor too just like me. I often noticed her and sometimes even stared. It did not go unnoticed by her and she made the first move to get introduced. Soon after, we were making plans...

Shemale
4 years ago
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first time with a shemale

Anyone who has read my other stories will know that they are based on real events, this one is also based on an actual event. It happened on a recent trip to Thailand.We arrived in Thailand on a Friday morning, looking forward to a well-earned break. Jaq and I worked long hours, and we lived for our holidays. We had decided to visit Thailand as we were both curious about the availability of good looking shemales.It had long been a fantasy of ours to try a threesome with a shemale and hoped this...

Trans
4 years ago
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My first time with a shemale

OK, I was wasting my time on shamble videos and pictures on the web for about 8 years! When I first entered a porn site I almost got sick, but soon I got really curious about it but didn't dare to click that button; couldn't explain why I wanted it so much though. Eventually I pressed it. I started with shambles alone, then shambles fucking girls, then shambles fucking shemales and end up with shemales fucking guys... I started loving it, watching it on a daily basis. My fetish for thong...

4 years ago
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My first encounter with a shemale

I am a straight guy who had never strayed before.. however i had been having urges over shemales and started wanking to shemale porn every now an again online. i have always been interested with my ass being explored but i never found men attractive. with shemales it was different. they are beautiful, slender but also filthy at the same time. it seemed perfecti had planned a europe tour some years ago and my first stop was amsterdam. after a few hours of roaming the red light district i was...

2 years ago
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me my daughter and a shemale

my last story was with my daughter for the first time now we both have shemale girlfreind very beautiful ones they would come over me and my daughter would put on our sexy heels she picks my shoes now lol and they would fuck us both on the same bed theses shemales are in good shape they would fuck me and my daughters tight lil asses and shoot globs of cum then they would watch us creampie it out one of them came over one night when i got off work my daughter wanted me to tougue out her shemales...

4 years ago
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.Quite by chance I...

4 years ago
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shemale on shemale

Hi dear it just a story may be its real cany sure some 1 told me & i write this 1 for u Hi mai ap ki friend ap ka leya aik or story la kar aee hoain, mujha 1st three stories ka jo respons mila vo to mai ko bata nahi saktee, par ap ka tnx zaroor kartee haoin dil sa. Isee ka sath maree 4th story ap ka leya. Ya mara sath hona wala aik ajeeb or anokha waqia tha. I mean really very different, mujha movie dakhna ka mood huva to mai cenma chalee gae wahan khelade 420 film aksha ki lagi thee new film...

Lesbian
4 years ago
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1st time with a shemale

I have always enjoyed playing with my ass hole, about two years ago I was in Chicago and went online to Eros and chose a shemale named with held. I called her up and she came to my hotel room. I was very nervous when I opened the door. She was about 6' tall and was a very good looking Latino. She bent down and gave me a kiss right on the lips and man where her lips where soft. She went into the bathroom and asked me to relax and she will be right out. I was lying on the bed and she came...

3 years ago
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First Time with a Shemale

This is a true story about my first time being with a shemale. I happened just over a year ago on the tail end of a business trip to Amsterdam. I had a couple of free days at the end of my trip to enjoy and explore the city. So naturally, I decided to check out the night life and that meant a visit to the Red Light District.I spent a lot of time just walking around and taking in the sights and sounds of the area. There were so many people walking around and it was alive with all their energy. I...

3 years ago
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Wife Fucked By Shemale

This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used to make me drink...

4 years ago
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Threesome In Thailand With Hooker And Shemale

Hi friends. It’s your favorite writer Abhay from Jaipur. Thank you all for the huge response for my last sex stories. Now I am back with my recent real encounter. You all know my vitals and so I am skipping that part. Suggestions and comments are always welcome. I respond to every email I get. So, let’s start with my real life incident. It all happened in May 2018 during my vacation trip to Thailand with my wife and another couple of friends. Our vacations were nearing the end and I wanted...

4 years ago
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Massage Sex With Latina Shemale

Hello, I happened to be on a trip to Brazil, when after my meetings, I went back to the hotel and took a nap. After an hour or so I was fresh and charged up, I decided to go for a massage. I looked at the online sites and fixed up a house call to my room, by the way I had chosen a transsexual for my massage. After an hour, Maria knocked on my door; I opened it and led her inside. Maria was around my height, with dark jet black hair, chocolate color skin, Though her breasts were not huge they...

Gay Male
4 years ago
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My First Time With A Shemale

Hello Indian Sex Stories readers, thank you for your continuous support. Your support helped me to experiment more and more with different kinds of people. This time it was an unexpected encounter with a shemale. I hope you like this one. Email me at & tell how hard I made you cum ;). And also if anyone from Mumbai or Thane want to have a session with me than you can email me without hesitating. I don’t judge people don’t worry. So let’s come to the story. This is a recent story that happened...

Gay Male
4 years ago
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wife fucked by shemale

This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used to make me drink...

2 years ago
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My first time witha a shemale

I was holiday in Spain with my friend and his Mum when i was 17, we didnt have any problems getting served in the bars so went out every night drinking. Half way through the holiday we all went out and me and my friend ending up in a club quite the worse for wear, a girl was dancing against a pole and keeped looking at me so i look backand maintain eye contact, she danced in my direction so i danced up to her and as she started to grind against me i started feeling her tits, she turned round...

4 years ago
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Passionate Sex with a Beautiful Shemale

Passionate Sex with a Beautiful Shemalea man and his shemale lover get down to businessWill led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing...

4 years ago
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First time with a Shemale

First off this is a true story. I lost my virginity at a young age so sex is always been something usual for me. As far as how I lost my virginity... thats another story. I have always dated women that were openminded, bi-sexual and down right sluts. I have been in strange conversations and situations because of being soooooo "openminded", heres my story... Bella and I were getting dressed for a night on the town. We had plans to meet a couple from a a website we were members of. So we were...

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