T-Girl
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.
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