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My first shemale experince - sex story


My first shemale experince



In my early 20's I was doing a lot of exploring of my sexuality and inturn had a wide variety of experiences. I had numerous partners, I tried just about every sex toy you could imagine at the time. But, I was also much skinnier then, i was 6'3 about 200 pounds. Looking back on this, I believe being that size allowed for me to be much more risque' about my encounters. To look at me you would never know I was bi sexual and could be a complete cumslut when the tide rose. I always knew that men would dress as girls did but I never knew that they could be so beautiful. (I was young).

I was about 24 when I met her, Sierra. A petite ebony colored skin shemale, about 5'6 and maybe 160 pounds. Sierra had breast implants and several other cosmetic surgeries done to include laser hair removal, she had her adams apple shaven down and she was on estrogen shots. Although, very slender Sierra had curves like a female gymnast. I was truly taken back by her. I would randomly see her in different places. i lived in Cocoa Beach at the time, in the mid 90's. I eventually introduced myself to her after about 3 weeks of running into her in public. At the time I didn't know she was a shemale, I thought she was a real woman, a very beautiful one. Anyway, I ran into her at the grocery store and we just happen to be in the same isle. She was wearing this yellow and white flower spring dress that just made her skin look so much darker, and at the same time showing her curves so much more.

She smiled back at me and said hello and asked me how I was doing, We started up an innocent conversation about something and I finally told her that I kept seeing her around town and found her to be very beautiful. She smiled and tilted her head down like she was shy and said thank you. Her voice was sweet and soft, not deep or manlly sounding at all. I asked her if I could take her out to dinner over the weekend and she shyly agreed and we exchanged numbers.

On Saturday night, as I prepared for our date I was showering and made sure that I shaved everywhere and being in my early 20's I was horny as hell. I always kept a suction cup dildo with balls in my shower to ride, an 8 inch realistic one. I applied some lube to it and slid it into my ass and rode it for a few minutes doggy style until I stood up a little bit and it rubbed on my prostate making me explode all over the tub without me touching my cock. I finished my shower and applied feminine lotion to my body( I forgot to use nonscented) and put on a mans bikini underwear and my dress shorts and a polo shirt. After blowing a huge load in the shower I was much more relaxed leaving the house but still a little nervous.

When I arrived at her apartment, I knocked on the door and when she opened it she had this red and white checkered Spring sundress on. It was low cut in front and back exposing the top of her C cup breasts and the back was cut so low that it was right above her panty line. Her hair and make up looked amazing and I just stood there in awe of her. The words beautiful and stunning just kind of fumbled out of my mouth. On the way to the restaurant conversation was easy, she told me she just moved here from Orlando and just needed a change of pace while staying close to her family. We enjoyed dinner at a seafood restaurant and had some drinks and just talked. I eventually suggested we go down to the beach and walked the boardwalk for a bit.

As we walked the boardwalk we came to an area that didn't have as many lights and we sat on the bench and watched the waves roll in and the mesmerizing sound of it. We sat for a while and I put my arm around her waist and she put her hand on my chest and cuddled up. A few minutes later while we were talking she looked up at me and I couldn't help but lean down to kiss her. Her kiss was soft and sweet, our tongues danced as we sank closer to each other. She turned and put both legs across mine and we continued to make out for what seemed like forever.

As we kissed our hands explored each others chests and backs. Her breasts were amazing. I could tell she had some work done but they were still soft and firm with about quarter size nipples and as thick as my the tip of my pinky finger. I moved my hand from her breasts to her thigh and they were like silk. I began to run my hand from her calves to her thigh and then to the top of her thigh for a while and then she just stopped me. I took me back jut a little because she had this worried look on her face. My cock was rock hard and she stopped me like I had done something wrong. She just looked at me for a moment and then she told me she needed to tell me something and that she hoped it didn't scare me away. I sat up a little on the bench and looked around and still saw no one, and she began to look like she was going to cry and I told her that she was safe with me. She kissed me deeply again and that is when she told me that she wasn't a full woman, that she still hard her penis. I looked at her in a confused way and I could see the fear in her eyes. She put her hand on my cheek and she told me that she really liked me and didn't want me to leave her like other guys have. i sat up just a little more while I processed what she had told me. Then my freaky perverted mind kicked in. I looked at her and leaned down and kissed her like there was no tomorrow. I could feel her tears on my face as I kissed her. I slid down a little on the bench to both relieve some pressure on my raging hardon but to also to invite her to straddle me.

I gently pulled her on top of me and she slid over me I ran my hands up her thighs to her ass cheeks. So firm but also so soft and her skin felt like silk. This is also when I could feel her cock press against my leg and OMG she was hung and thick. She had it tucked up and under and behind her thighs. As She straddled me I run my hands up her thighs and up to her tight ass, I gave it hard squeeze and she let out a little squeal and giggled. I slowly massaged her ass and gently ran my finger tips over the head of her massive cock. When I did she let out a slight gasp and squeezed my neck a little harder. I continued to tease the head of her cock for a few more minutes before I reached under her and ran my fingers the entire length of her cock. About half way down I felt something that felt like silk around her cock and running up behind her. I fillowed it up her ass cheek and felt it tied to her lace thong, I untied it with one hand and let her cock free. Her breathing started to get even heavier and she became even more affectionate. With her straddling me her cock began to hang between our legs now and I could feel it rubbing the inside of my thigh. I reached underneath us and slid her cock into the leg of my shorts in case anyone walked by.

We made out on that bench for over 2 hours impervious to the world. Both of us were as hard as rocks and ready to burst. I could see about 50 or so feet away a couple standing in the shadow playing with each other and watching us. Sierra giggled a little bit and whispered in my ear if they really knew what would they do. I chuckled and kissed her again. He lips and perfume were intoxicating. Her body memorized me and that cock had my filthy mind going wild. Just then she looked at me with this crazy look in her eyes and whispered to me that if they wanted a show we should give them one. A little confused as to what she meant I went with it.

Still straddling me she reached down and opened my belt and shorts and told me to lift my ass up. I did as I was told and then she saw my bikini bottoms and got a look in her eye like she was trying to figure out why I was wearing a bikini bottom. But she didn't miss a beat. She pulled my shorts down to my ankles and ran her hands up my thighs. I glanced over and the woman had her husbands cock out stroking it while he had his arm around her playing with her pussy. I looked down at Sierra as she reached up to my cock and she lifted the side of my underwear and pulled my rock hard cock out and then she realized that I was completely hairless and I got another inquisitive look as she came closer and licked the bottom of my cockhead. I let a moan and placed my hand on the side of her head. She began to start licking and kissing up and down my shaft and swirling my balls around with her tongue. Her lips and mouth felt so amazing that all I could do is put my head back and enjoy. A few minutes later she took my cock in her mouth and cupped my balls with her other hand. Her lust, at that point, went into overdrive and she began sucking my cock wildly. After about 30 seconds of that I felt her push my thighs further apart and the hand massaging my balls started to slide down to my ass. I was so close to blowing a massive load as soon as she began playing with my asshole I tensed up and blew my load in her mouth, she swallowed a few times but couldn't keep up. I couldn't stay quiet anymore when I blew and let out some crazy gutteral noises. As I started to calm down I looked over to the couple watching us and he had his cock buried in her pussy doggystyle fucking her wildly.

Sierra looked over as she cleaned up my cock and watched him unload into her pussy as well. Sierra took her time cleaning my cock and balls up with her tongue. When she was done she leaned up to me and I met her half way and gave her a deep sensual kiss. I could taste my own cum on her lips and all we could hear was the female say "OH Fuck that is hot." We giggled at each other and decided to get out of there. As I get ready to pull my shorts up she pulls my underwear off me and tells me to go commando. As she stands up her cock is still swinging between her legs and reach up under dress and slowly massage it. She wraps her arms around my neck and starts kissing me again as I stroke her massive cock. The couple was still watching us and I could only guess that from that far away it looked like I was fingering her pussy. But I kept stroking her and as she moaned into my mouth and begged me to make her cum. I reached around under her dress and with one hand massaged her ass and with the other storked her cock with long strokes. I decided to return the favor she gave me and I licked my middle finger slathering with saliva and I reached back around her and slid my finger into her tiny little asshole. She gasped and kept saying "oh baby oh baby, yes baby" and I slid my finger into her ass she collapsed into me blowing a massive load all over the ground beneath us. I kept gently stroking her cock and swirling the head of her cock in my palm making her jerk involuntarily, making it look like she was having multiple orgasms to the other couple.

The other couple quickly pulled themselves together and left. We stayed a few more minutes and she continued to straddle me giving me gentle kisses. This is when she leaned back and looked at me with the same inquisitive eyes as before. She asked me why I was completely shaved and why didn't I run away when she told me about her situation. I looked in her eyes and kissed her again and asked her to follow me back to my apartment and I would explain everything.

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