Today our dear reader Marc tells us a story about how he met his first and the only transsexual lady in life.
Way back in 1988 I was a poor student in New Zealand, my first year at Auckland Uni and going it alone in terms of study fees and books. I had a bad toothache and couldn’t really afford to see the dentist. I put up with the pain for so long until me sister suggested I call a friend of hers called Jenny. Jenny was what we call in NZ a School Dental Nurse, all kids are entitled to free dental treatment until they reach 18. I had met Jenny several times over drinks at parties, her and my sister were close friends. I actually liked her and found her quite attractive, a little aloof, very smart as well. I mean she was after all a health professional.
So I called Jenny and she agreed to see me and examine my sore molar. However it had to be done after hours as she was well outside her contract rules in seeing a poor 19 year old student. On this particular day I pulled my old clunker Toyota up outside the school dental clinic in Auckland at about 5.30, in those days she smoked and was outside the clinic having a cigarette. She used to get ridiculed by her friends at clubs and pubs as a dental nurse who smoked. It didn’t bother me in the slightest, I just wanted my tooth bloody well fixed. She greeted me outside the clinic with a peck on the cheek like an old friend and joked that this was going to cost me a night out at the pub.
Fine I agreed, that was cheaper than the $300 I had been quoted by a frikken dentist. She told me to go into the clinic and get comfortable, she would be in as soon as she finished her smoke. I was never comfortable in the old school clinics, some of the nurses had real attitudes back when I was at school. But Jenny had a good reputation. Or so my sister told me anyway.
Jenny followed me into the clinic a minute later and began to pull on her gloves, something that deep down I had always found arousing, don’t ask me why! She took up her pick and mirror and began to examine my teeth, locating the affected one and all the while talking to me. Silly stuff like, “you seem to spend a lot of time looking at me when we are at the pub etc”. I am trying to reply with my mouth full of fingers covered in rubber gloves and going more than a little red. Thinking oh shit how do I get out of this my sisters good friend and all. Anyway she had the tooth drilled and filled in about 5 minutes and then explained that she wanted to know more about me and all.
So as I am sitting there in her chair, more than a little embarrassed now and a little shy as well. But did actually fess up and said well I do think you are attractive, really she replies because I have been having a bad time of late with boyfriends. The thing is that I am more than a little aroused and she knows it, she carries on probing me about all sorts of silly stuff all the while rubbing my hand and then shoulder. Maybe to get me to say something more. Her hand then begins to trace down my stomach and rests on my jeans zipper and goes hmmm. I cant believe where this is heading now, I mean she was damn cute, stood about 5ft 7″, firm little breasts, a quite curvy at the hip area, nice tight little bum as well. She would have been 27 then…
The next thing she is stroking my cheek with her other hand. Now I am seriously in the mood and cant believe my luck and just where this is going as my zipper is being slid down and those gloved fingers wrap around my rather stiff member as she continues to snog the living daylights out of me. I am starting to think there is an accident coming up here and a mess all over the bottom of my shirt. She then breaks snog mode and says, you are comfortable with this aren’t you? Of course Jenny I squeak, good she replies and slowly lowers her head down to where my stiffer than stiff dick is sticking out of my jeans. Suffice it to say within 2 minutes she is spitting into the bowl next to the chair as I am contemplating the next step.
She zips me up and says, right let me get changed into something more civilian here and you can take me to Sergios Bar. She disappears into her side room where she has a locker and reappears minutes later in a short leather mini skirt (her trademark), high heels and a red roll neck sweater thing looking like a million bucks, leather bag on her shoulder. She pecks me on the cheek again and says take me down town Marc. I cant believe where this is heading. We climb into my clunker, she asks if she can smoke it, I agree, she lights up and we head downtown… The bar is 3 blocks from her apartment which is quite convenient as we drank far too much red wine in the cooling autumn evening and with the rubbing of the thigh and the closeness of her to me I am just back in that mood again. She is very feminine, she smoked in a very delicate way, she holds her wine glass so lady like and the continual fluffing of her hair off of her collar is just so damned, well ladylike. She did say to me at one point, so how much has your sister told you about me. I think I replied not much, you are very intelligent, quirky, cool to be with and a good friend to her. Oh really she replied!
At about 11 pm she suggest we walk the short distance to her apartment, the walk will do us good she says and we need to be just a little more sober don’t we? With something like you never know what may come next? Her apartment is very modern and we step into the living room from the front door where she kicks off her heels and turns to me and locks her lips onto mine and snogs me hard in seconds. Within minutes we are in her bedroom and she excuses herself to use the bathroom and put on a negligee as I strip and climb into her large bed. 5 minutes later she has blown me for a second time that day some 5 hours since we first met as she moves to the balcony to smoke another cigarette. When I was washed up and join her on the balcony we talked more and then began to pash some more this time my hands are working over her breasts and slowly move down to her mons. That was when I found her package, I was initially shocked and she said then I should never have led you on, I am sorry.
But now I am rock hard and think what the hell. We moved back to the bedroom where I made love to her 3 times, she was like a tiger in bed and so long as I was working her stiff clit we were cool. She needed to be hard to enjoy sex. I never felt bad or embarrassed about what I did, I never told me sister though.
I saw her for another 5 months before she took a transfer to another city and school. Jenny was cool and taught me a lot about myself. I have never had another transsexual since, but I would if I had the opportunity!
Post tags: blowjob, reality, sex, tgirl, tranny
Cute story; very nice.
i just came reading this!
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Well-written and erotic. So many angles!
if i was you i would be looking up jenny again.