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Introduction:

My first shemale experience....but not my last.

This is my first story, I would love any and all feedback. Thanks



This day started off like any other however it will end with a fantasy being fulfilled….

I woke up with my traditional morning wood and like most mornings I reached over and grabbed the lube bottle and slowly poured a healthy dose of lube all over my throbbing cock. Some of the lube made its way down the crack off my smooth ass and slowly ran across my tight asshole. I loved the feeling of my asshole getting lubed up…..I decided I wanted to be more adventurous then normal, so I reached into my “soon to be ex-wifes” nightstand and pulled out her favorite pink dildo. I lubed it up and swirled the head around my now very excited asshole.

While I was stroking my cock with one hand I slowly pressed the 7” inch dildo against my puckered ass. My wife had pegged me before but this time felt different, this time I was wishing that the hard cock pressed against my ass was attached to a man…..As the head pressed into me I was thinking about how amazing it would feel if that was a real cock. After a few pumps I was able to get the entire dildo deep into my ass. I was thinking how it would feel to have a hard cock fill my ass with cum…that thought drove me over the edge and I shot my load all over my stomach, I came so hard some even reached my chin!

I put some on my finger and licked it off, I knew what my jizz tasted like because my wife liked to spit it into my mouth after she sucked my cock. I slowly pulled the dildo out my ass and then played with my hole with my fingers for a bit. I then got up and got ready for my business trip. I was an a vice president at a accounting firm and I was going to attend a conference in Florida.

When I boarded the plane I noticed that they was a very attractive lady sitting in my row. I sat down in my seat and said, “Hi how are you?”, my row mate said, “Hi, I good thanks, my name is Kendall”. I learned that she was going to the same conference I was headed into in Miami. She was beautiful, perfect B cup breasts, I tend to prefer smaller breasts, cute ass and was very petite, which I love. I found out that she was newly single and also had an apartment in Miami that was located in an area that had a lot of gay nightclubs. We exchanged numbers and planned on meeting for a drink at some point of the next couple of days.

When we got off the plane I was walking behind her and couldn’t keep my eyes off her ass, I think she noticed because she seemed to start wiggling it a bit more. When I got to my hotel I unpacked my bag and decided to take a shower. I couldn’t get Kendall out of my head, my cock started to throb just thinking about that perfect as and perky little tits. I couldn’t help but stroke my cock thinking about licking her tight light ass and driving my cock inside her. I started stroking faster and faster until I felt my cock started to drip, I gathered up as much as I could on my finger and then licked it off. My cock was dripping like never before, I put more of my precum on my finger and then swirled it around my asshole. As I slide my finger in my ass, using my juices as lubricant, I exploded all over glass shower door. I watched as my cum slowly dripped down the shower door, I got on my knees and started slowly licking my cum up. I started to wonder what another mans cum would taste like…. I was in the right town to find out.

After I got dried off, I checked my phone and had a missed call from Kendall. She had also texted me and asked if I wanted to meet her for a drink. I of course immediately texted her back and said I would love to meet her. She told me to meet her at a bar that was close to her apartment. I told her I’d be there in about 30 minutes. I got dressed and my mind started racing about what the night might bring. You see, my about to ex wife and I haven’t had sex in over a year, it turns out that she discovered that she was a lesbian and wanted to be with a woman instead of me. At first I was hoping to get her to invite a girl into our bed but she wasn’t willing to share her girlfriend with her husband. She was agreed to get a divorce, its not ugly or anything, we still care about each other but there is zero touching going on between us.

When I arrived, I found Kendall seated at the bar, she apparently had already had a few cocktails. She looked amazing, she had on a short skirt which showed her amazing legs, a cute top that showed her tight stomach and really showed off her perfect tits. I ordered my usual vodka and sprite and we found a table in the back and sat down. We talked about business stuff and what we thought the conference would be like, she was new to the industry but was eager to learn.

As the drinks kept coming the conversation got more and more flirtatious. She asked if I was married and I explained that I was but we are getting a divorce to technically I’m on the market. She laughed and said that she was in a relationship for about 5 years and then she realized they had fallen out of love and decided to move on. We were both pretty tipsy by now and she asked me if I’ d like to come over to her place for another drink. I said sure, so we left the bar and started the 3 block walk back to her place.

While we were walking she noticed me steal glances at her tits and perfect ass. She asked me if I liked the way her ass looked in her skirt. I glanced at it again, since I had a little liquid courage in me, and told her that she had the best ass I’d ever seen. She grabbed my hand and placed it on her tight butt cheek. It felt as perfect as I had imagined, I ran my hand all over her ass…my cock was trying to jump out of my pants at this point. She noticed the bulge and kinda smirked, she smiled at me and licked her lips.

As we got about a block from her place I noticed that there were mostly gay couples around us, men making out with men (which I found so hot), there were stunning transvestites in sexy outfits, it was all new to me but I was so aroused by it. She noticed me checking out the guys kissing and the hot shemales strutting around. She asked me if I liked that kinda stuff, I didn’t know what to say, I told her it was new to me but it kinda turned me on. She smiled and said she had a surprise for me when we got up stairs. I smiled, grabbed her ass again and told her I was looking forward to it.

When we got in the elevator in her apartment building, she grabbed me, pushed my up against the wall and drove her tongue into my mouth. I reached down, grabbed her ass and pulled her into me, the feeling of her tongue against mine made my cock even harder than it was before. When we got to her apartment she made us both a drink and we sat down on the couch. She started rubbing my thigh and told me how attracted she was to me. She leaned in and kissed me, much more seductive and sensual this time, with passion and lust like I’ve never experienced. She slowly pulled away and excused herself, she went into her bedroom and shut the door.

I was sipping on my drink and slowly rubbing by throbbing cock thinking about what Kendall might be up to in there….then the door creeped open and I heard her say, “come to me”. I quickly got to the door and saw her standing in the sexiest lingerie I’d ever seen. She had her back to me, she had a white g-string on, a sheer white top and white high heels. I approached her and gently grabbed her ass, but when I went to put my hands around her waist she grabbed my hands. She said, “remember I said I have a surprise for you when we get to my place?”, I said “yes, I remember” she said “well, my name use to be Ken” and with that she slowly slid my hand down to what was the biggest cock I’ve ever seen.

At first I was very taken back and pulled my hand away, she turned to me and said she was so sorry for misleading me. She got a very sad look on her face and told me that she was so attracted to me that she couldn’t help herself, she knew it was wrong but really wanted to feel my cock inside her. She turned away from me and continued to say how sorry she was, she told me that she would understand if I left and never talked to her again.

I walked up behind her, wrapped my arms around her, hugged her and tuned her to face me. I gently placed my hands on her face and pulled her into me, I kissed her deeply and passionately for what seemed like an eternity. I slowly ran my hands down her body caressing every inch of her, when I got to her 9” throbbing cock, I stroked it slowly and massaged every inch of it. I felt some precum on my hands as I got near the tip, I licked it off and then kissed her so she could taste her cum.

I them slowly undressed her, as I slid her panties off I licked the head of her cock so I could taste her juices again. She let out a loud moan, she then grabbed my head and forced her cock in my mouth. I gagged on her huge piece of meat but I loved the taste and feeling of having a warm pulsating cock deep in my mouth. While I was sucking her cock I started to caress her ass, only to discover that she had a nice big butt plug inserted deep in her cute little asshole. I pushed on it and noticed when I did I felt juices drip from her cock.

She told me to get on the bed, so I slowly took her cock out of my mouth, stripped off my clothes and lied down on the bed. She slowly stripped the rest of her lingerie off and climbed on to the bed. She ran her hands up my thighs and pushed my legs apart. She licked my inner thigh and slowly licked my balls, sucking on each one gently. She them grabbed my cock, and in one shot took it all the way down her throat. I thought I was going to cum immediately but I was able to hold off, mainly because I wanted to shoot my load into her amazing asshole.

I grabbed her and spun her around so I could taste her cock again. She started pumping her cock in and out of my mouth, with each thrust I was able to take it further and further down my throat. I reached up to her ass and slowly pulled out her butt plug, I then slide one…then two….then three…. And finally four fingers deep inside her ass. I felt her body start to buck on top of me, I knew she about squirt a load of hot jizz down my throat. I started sucking her cock faster and pushing my fingers deeper into her asshole, then I felt her cock pulse, she screamed and shot a huge wad of cum deep down my throat. It tasted amazing and I swallowed every drop, I kept sucking hoping to get more of her hot jizz but she got off me and told me she wanted to feel my cock buried in her man pussy.

She got on her knees and I knelt down behind her, I slowly but forcibly slide my cock inside her tight ass, grabbing her tiny waist and perfect tits, I thrusted my cock deep inside her bowels. I reached around and found that her enormous dick was hard again and begging to be stroked. I slide my hand up and down her cock as I pumped my cock in and out of her tiny little butthole. Her moans got louder and louder and I could tell she was ready to cum again, but I stopped stroking because that load was meant to be inside my ass. I wrapped my arms around her waist and fucked her as hard as I could until that one last thrust and shot a huge load of my sticky hot cum inside her ass.

I pulled my cock out of her, laid down next to her and kissed her deeply. I told her that I wanted to feel her inside me. She got up, got between my thighs, pinned my knees to my chest and started licking my ass. It was the best sensation I had ever experienced….yet. Once my hole was nice and lubed up from her licking me, she slide her middle finger deep inside my ass…then another finger…and another….until she was 4 fingers deep inside me. She asked me if I was ready for the real thing and I moan and told her to stick her cock deep inside me.



She slid up between my legs, aligned that huge meat log with my ass and slowly inserted it into my gapping ass. I gasped as the huge mushroom tip or her cock penetrated my virgin ass, she slowly but powerfully slid her entire cock in my ass....I was seeing stars and my pulse was racing, I couldn’t believe that I had a hard cock inside me!! She was pounding my ass with everything she had, she drove her cock as deep into my ass as she could and then paused...she leaned in and gave my the most passionate kiss I’ve ever experienced. Apparently the kiss turned her on as much as it did me because I felt her cock pulse inside my ass and then I felt her warm cum fill my no-longer-virgin tight asshole. She slowly pulled her cock out of me and her cum poured out of my ass.

We kissed and held each other for quite a while, finally we got and headed to the shower. We cleaned each others bodies off and kiss each other all over. As I got ready to leave, she stuffed a pair of her used panties in my pocket and told me that the next time we meet she wants those to be covered in my cum. I kissed her, thanked her for the most amazing experience of my life and told her that i would love to see her again. She winked at me, grabbed my cock and told me that what we did was just the beginning of what she wants to do to me.....

The conference is a week long...and that was just the first night....

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