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Thread: My first time

  1. #1
    Junior Member
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    Default My first time

    So this is the story of how I lost my virginity to a t-girl. It begins sometime before the actual event in the last days of my marriage to my ex.

    Me, I am a 36 year old regular white collar Joe. I was married for nearly 12 years after a 3 year courtship period. Never could figure out how the cute girl I ustd to date turned into this nagging, argumentative lady. The only thing that held the marriage together that long was our daughter. Anyways, increasingly frustrated and having to deal with a passive sex partner I turned to porn. Especially to porn or fetishes where the lady was a proactive partner. Like strap-on.

    One day while surfing strap-on videos I accidentally stumbled upon one with a t-girl. She was so pretty and feminine I could not believe my eyes. And when she came I was hooked. Her climax meant she enjoyed the experience equally and was actively gaining pleasure from it. I graduated from more tgirl videos to online chat.

    Finally, sometime after my divorce last year I ventured to meet a tgirl hooker. I selected one who looked feminine. Any masculine look is a mood killer for me. But when we got to the room I kind of chickened out. I settled for a massage with a happy ending. Then asked her to masturbate, which she did. When she was about to cum she surprised me by suddenly standing up and shot on my chest. Very naughty but that felt so hot. I then ventured to feel her penis. (I hadn't touched till then by the way.) As I gently tugged her sticky tool, she ruffled my hair and called me "cute"!

    Now ice broken, and not comfortable with hookers I got to this dating site sometime back. There I met this cute tgirl. She is about 5'5", 24 yrs, straight brown hair with pretty, girly face. Kind of young for me but its okay. Nothing serious or exclusive. So anyways we go out on a date and I treat her nice. I can afford to. Even paid for some of her shopping. And she was happy.

    The first two dates we did not proceed beyond a little kissing. Funny thing, I was the one reluctant to proceed further. It was like the roles had been reversed from my previous dates! Third date we go to a movie. Nice corner seats and most of the seats were empty. Little into the movie she made her move. Started kissing my neck and feeling me up. I reciprocate and she moves her tongue into my mouth. The kissing was so hot, passionate. My hand was nestled on her boob. She takes it and guided it southward. As I rubbed her over her jeans, I felt her squirm and start to stiffen. Touching her cock felt nice. But I was still unsure and moved my hand to her thigh in some time. She took my hand back and firmly placed it back on her tool. I start rubbing and squeezing.

    'Baby", she whispered,"can I get a handjob?". I looked at her in surprise, "Now?". "Please" I looked into her pleading eyes and acquiesced. We unbuckled and unzipped her. Pink panties nicely filled up. As I felt over her panties I could see it had gone moist. I released her and looked at her dick for the first time. Nice, long and slender. I move my hand along her hardness while pretending to watch the movie. She guides me about the pace and movement she likes and I follow. In a few minutes she climaxes and I feel warm load on my hand. The whole thing feels bits surreal and so good - the thought of her pleasure from my hands.

    She then took out a few tissues from her bag. Hands me some and I clean my hand. Her cock is still hanging out and she hands me some more napkins. She wants me to clean her up too. I gently clean her up and tuck her back into her panties. She zips up and unable resist, I give her now covered cock a gentle pat and cheekily say" Good girl." I am rewarded with a smile.

    Continued....


    6 out of 6 members liked this post.

  2. #2
    Junior Member
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    Default Re: My first time

    ...Continued


    Nothing further happened on that date but hectic sexting followed. After a few drinks on our fourth date we get back to my place. She is wearing a black dress and heels. She plops onto my lap and we frantically make out. She then gets up and starts to do a little striptease to my enjoyment. Once she was down to her lingerie (sexy one, I may add) she pulled me up and demanded that it was her turn to enjoy now! So I started giving her a goofy strip tease and she couldn't stop giggling. When I am down to my birthday suit she motions for me to turn around slowly. I turn around and I feel her grab my butt. She kneads my cheeks, kisses them, runs her tongue over my hole and playfully spanks me for a few minutes. This is the first time in my life that someone worshipped my butt and boy did it feel good. After a few minutes, she turned me around and started to blow me. She sure knew what she was doing and it felt so good. I had to actually ask her to stop for fearing of losing it too soon.

    We moved to the bedroom. She led me to bed by pulling on my raging hard on. Once in bed, she slipped of her panties. She was soft and I noticed that her flaccid one was longer than my erect one. Wow, I was impressed. (She is not much of a grower). I took a good look and decided to do something about the flaccidness. Before I could think about it and hesitate, I dove down. I started with a few kisses before engulfing her with my mouth. It tasted, like well, skin. She again guided me with useful tips-run your tongue along the shaft, suck my balls, try taking deeper etc.- and I was a good learner. She got hard very quickly. I did not really deep throat but think I did okay for starters.

    She then asked me to turn around. I did as told and saw her slip on a condom. Interesting how this worked out, we never discussed who would top or bottom, she herself had said that she enjoyed both. I just went with the flow and let her be in charge. She nudged me to stick my ass out and spread my legs apart. I then felt her lubricated finger enter me. "Ooh, you are so tight" she cooed appreciatively. After working me for sometime with her fingers, it was time for her to enter. As I felt her tip touch I clenched instinctively. "Relax", she commanded.

    I tried my best to distract my mind and relax. She was gentle and slow in entering. But it felt uncomfortable and painful. I kept calling out to stop. We stop-started a few times after a few thrusts. Finally I gave up feeling it is not to be. I could sense her disappointment and moved to appease her with a blowjob and a wank. She came in a bit and tried to return the favor, However my cock seemed to have grown limp by then and did not respond. I gave up (seemed just not my night) and hit the shower. We went to sleep while watching some TV.

    Who is this disturbing my sleep? I sensed something hard rubbing against my behind and gently pinching my nipples. This beautiful girl was spooning me! I felt incredibly turned on. I reached behind and sure enough, her member was all stiff. She started kissing the back of my neck and the pace of her thrusting increased. I turned around and we kissed. Soon we were all over each other. She suddenly sat up and I bent over. She yanked down my boxers, slipped on a condom and entered. She slipped right in. Furious thrusting ensued doggy style. It was rough, she kept slapping my ass and pulled my hair. I had no control, I was swept in the moment. I was being used as a bitch by this girl! She came inside me and with a moan bent forward and hugged me from behind. Her cock was still in me and I could feel her boobs on my back. Loved it!

    I was completely turned on by then and wanted my shot. We switched positions and I entered her. She fit wonderfully around me and she kept clenching and relaxing her muscles which shot joy through me. She kept making encouraging noises. I had a very satisfying cum all over her ass.

    There, it took a furious early morning romp took care of my virginity after the earlier frustration. My inhibitions were overcome. We both fell to deep slumber.

    I woke up first and freshened up a bit. I then went to wake her up. She was sleeping stark naked. (later came to know that she is naked a lot even when awake at home! More on that maybe some other time). I looked down and she was making a tent in the sheet! She opened one sleepy eye at me and smiled. Then she took my hand and placed it on her morning wood. She wanted me to take care of it!

    I decide to tease her. I say, "What is the magic word?".

    "Oh baby, no blue balls please". Haha, I need no further convincing.

    I get an idea and take out the massage oil. I apply it liberally on her cock and balls and start to massage her tools. I gently apply strokes and cup her heavy balls. Massage her perineum as well. She was still half asleep and the look on her face was pure bliss. I bent down to sucked her boobs and a sharp gasp escaped her. She was now quivering all over as I gently built her climax. I loved this feeling of giving pleasure- it was one I hadn't experienced in the longest time. Her climax was an abrupt blast- I never seen so much cum in my life (real life, not counting porn ).

    She shot right up and smack hit my face, hair and chest. A great deal oozed onto my hand. She came for several seconds. I kept rubbing and gently drained out the last of her. She saw cum-covered face and let out a giggle. I laid down with my head resting on her boob (they made a nice pillow) and my hand still held her member while she ran her hand through my hair.

    "Baby", she called out. I looked up at her. "Why don't you taste me?"

    Hmm, why not...that was the only thing left.

    So I take my hand and without breaking eye contact I licked her stuff clean off my hand. I could see that she loved it. She reached out and collected the cum on my face with her finger. She then placed her finger on my lip and I sucked it dry.

    "Guess you are my slut now", she said, seeming pleased. I smiled.

    "Taking your cherry feels so good. I will always be the first. Guess you might as well tattoo my name on your ass, Mister!!"

    Funnily, that evening I got intimate with this chick (an actual lady). I was so heated up from my earlier romp that I was an absolute Rockstar in bed! Lol.


    6 out of 6 members liked this post.

  3. #3
    Junior Member
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    Default Re: My first time

    If you like this, I got a couple more to tell.


    3 out of 3 members liked this post.

  4. #4
    dddavido Rookie Poster
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    Default Re: My first time

    Hey that is a great story and well told. I would definitely like to hear more. I have ever only had one ts gf and the rest have been ladyboys from Thailand so this was just so great as it made me realise how good a ts gf relationship can be.



  5. #5

    Default Re: My first time

    What site did you meet her on? I am interested in meeting one for a relationship as well, but have no idea where to go? did you have to pay for the site?



  6. #6
    Junior Member
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    Default Re: My first time

    This was very well written!



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