First Date   added 8 years ago
  By: jess  Age: 40  Country: United States

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Rate by The Naughty Meter
Categories: Transvestites
Tags: TGirl cum oral blowjob
Location: Anywhere
Roleplay: Other
Fulfillment: I will tell you later
Nature: I will tell you later

This was always my fantasy when I was internet dating a few years back.

After a week or so of exchanging emails there seemed to be a bit of a spark between Joelly and I and we decide to meet at a local bar. Lucky for me, she turns out to be much prettier than the pictures she has on the dating site. Although she had listed all her sizes, I was a little surprised as she was built larger than I had thought. Well proportioned though, don't get me wrong. Beautiful brunette hair in a style just short of her shoulders. She wore a little lace up crop top and man did she look good in those jeans, like she had been poured in to them. I'm sure that she was noticing I had a hard time keeping my eyes off of the butterfly tattoo that peeked out near her cleavage. Every once in a while, she would lean in so that I could see beneath her shirt just the top of the lacy pink bra that held her beautiful breasts. She was teasing me and I loved it.

We shared a few drinks over which we got to know each other a little better. We had shared a bit about our backgrounds over email so things went very easy and I was having a great time. I told her I thought so and she agreed. A few drinks more and it seemed like the night was winding down. I was disapointed that our evening was coming to an end and I offered to walk her home. She thought that sounded nice and let me. At her door, I told her I had a nice time and asked if I could kiss her goodnight. She said that would be nice and we kissed. Softly at first and the more passionately as she began to explore my mouth with her tongue. I pulled her closer and kissed her back. I was begining to get excited and wondered if she could feel my growing hard on.

I pulled away and thanked her for a nice time, expecting that at this point I would have to go home and satisfy myself while I thought of how she looked in her jeans. Suddenly the look in her eye was almost devious as she said that maybe I shouldn't go and I should come in for a cup of coffee. I didn't even hesitate and immediately agreed. My luck in the dating scene was turning around I thought as this beautiful girl began unlocking the door to her building. I followed her in and once in the elevator we kissed more. Harder this time and more insistantly. I kissed her neck and ran my hands down to her tightly covered ass. I gave a little squeeze and just as I was about to reach for her breast the elevator came to a stop at her floor and we exited for her apartment.

It seemed to take forever for her to let us in but once she did I was all over her. Kissing her and pulling her close to me. She reached down and began to massage the growing evidence of my arousal. I could barely stand it as she stroked me through my pants. I pulled her shirt up to reveal that pretty pink bra she had been teasing me with all night and planted a kiss right on her butterfly tattoo. She seemed to enjoy it. Moaning softly as she held my head to her chest. I let my mouth travel all over her chest and neck, stopping only to kiss her mouth while she continued to make me harder.

She stopped rubbing my crotch to remove her bra and I began to suckle her nipples, first one then the other. She began to undo her jeans and strip them down past her hips while I continued to lavish attention on her beautiful tits. I reached down to grab her ass that was now free of her jeans and it was spectacular. Firm and round and perfectly sized. I grabbed her ass and pulled her towards me while I continued kissing her. She led me to the couch and we fell back on to it, barely separating ourselves from one another.

I leaned on top of her on the couch and began to kiss my way down her firm stomach toward the sweet folds hidden by her panties. Her hands played in my hair as she gently guided me down towards her lap. I looked up at her just before I reached my goal and hooked my hands into the waistband of her panties. I looked at her as I pulled them down slowly working them past her hips. When they were about at her knees, I finally looked at my prize. I was stunned.

There instead of the sweet folds of her womanhood was a cock. Bigger than my own and getting bigger by the second.

I sat there on the floor before her frozen, unsure of what to do. She took the opportunity to remove her panties the rest of the way and began to stroke her dick which was now getting fully hard. I tentatively reached for it. My body reacting on it's own while my brain reeled with confusion. She took my hand and placed it on her growing cock and gently guided my grip up and down her tool. I leaned in a little, staring in disbelief. Looking up at her face, I could see she was clearly enjoying the feeling of my hand on her prick.

I looked back at her hard dick in my hand. She massaged her own breasts while I slowly jerked her off. I realized at that moment that I was hard as a rock. Possibly harder than I had ever been. I leaned in for a better look and then her hand was on the back of my head. Pulling me down towards he meat. It wasn't so much her strength as my lack of resistance as my head got closer and closer to her dick until there was nowhere for it to go but in my mouth. I opened my mouth and felt the heat of her hard on slip past my lips. She pulled my head down a little more forcefully as her cock twitched in my mouth. I pulled away slowly and she pulled me back down.

Each time I went a little deeper, feeling her cock slide further and further into my throat until she was forcing my head down into her crotch with her long hard dick buried in my throat. I could barely breathe with it there but each time I pulled back she brought her hips up and pulled me back on to her. This continued until the pace increased to a rapid fucking of my mouth. She moaned loudly as she speared my throat with her cock ramming her tool deeper into my throat. I began to lose myself in the moment, slobbering on her cock and chasing after it with my mouth every time it popped free.

"That's a good little cock slut," she began to tease, "suck it. Make me cum baby."

I didn't even think about the fact that I had never sucked a cock before, let alone tasted cum. I wanted it, I wanted her sweet cum in my mouth. I began to jerk her cock while I sucked for all I was worth. She continued moaning and calling me names like cum whore and cock slut and it only made me more hungry for her cum.

It didn't take long until she began to tense up. She grabbed my head and held me still while she bucked her hips into my face a few times before exploding into my mouth. Her cum filled my mouth and I instinctively pulled away, taking the last shots of her load on my face. She coaxed the last bit of her seed out onto my face while I knelt there before her, mouth instinctively open.

"Mmmmm," she moaned, "I'm glad I met you."

"Me too," I offered while I savored the taste of her load.

But the night doesn't end there

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