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Chapter 01: Paul and Mag
Hi, my name is Paul and this is the story of my first time, sort of.
*
I discovered transsexual women completely by accident when I was 18. I was watching one of those Real Sex shows on HBO, and without warning, two women who were showering together for a video shoot turned around and I was shocked when I saw cocks where I expected to see pussies. What probably shocked me even more was that seeing these two beautiful women with cocks between their legs turned me on. There were these two wet, glistening, ultimately feminine women with penises, organs that my mind told me shouldn’t be there, but somehow didn’t look out of place. In the three years since then, I have fantasized about having my first date, my first kiss, and someday my first sexual experience with a transsexual woman.
Every once in a while I go to a particular adult store a few blocks from my home, called Pandora’s Box. Along with being the closest adult store to where I live, it also has the largest selection of transsexual porn of any I have been to. I work well into the evening, never getting off earlier than 8 o’clock, so when I do stop there on my way home from work, it is usually fairly empty. There are two people who are there almost every time I stop in, two women. Barbara, a short blonde, about 5’2″, always works the register. Maggie is taller, maybe 5’8″; she has dyed hair; so black it makes even her olive skin seem almost devoid of color. She is always out on the sales floor, usually stocking the shelves. Both of them are so beautiful that they should be models instead of working here, and both are refreshingly down to earth considering how gorgeous they were (in my experience, the more attractive a woman is the more she believes she has the right to be an asshole to everyone).
On this particular evening, I walked into Pandora’s Box on a mission. I was looking for a specific title, “Shemales in Paradise,” which an online friend of mine told me was absolutely the best transsexual porn movie she had ever seen. The plan was to pick up the movie, grab some fast food and go home to enjoy a critically acclaimed film.
I walked in about 9:30 and headed straight for the section reserved for new releases. After some searching I found “Shemales in Paradise” grabbed it and walked to the register. For the first time I could remember, Maggie was running the register. “No stocking for you tonight?” I asked.
She responded, “I’m off at ten tonight, so I decided to run the register for once and make Barbara do the stocking. Just this one DVD for you?”
“Yeah, just this tonight,” I said.
Noticing the title Maggie said, “Hmmm, you’re into transsexuals?”
Blushing a little, I said nervously, “Yeah.”
She looked surprised and said, “I think that’s sexy. You have any plans tonight?”
Tripping over my tongue, I said, “Sexy, really? No, I don’t have any plans other than grabbing some dinner and watching a movie.”
“Well, since I’m off in less than half an hour and I have been wanting to see this movie, would you be willing to wait for me and we could go watch it at my place? I’ll even make us some dinner.”
I was shocked to say the least. Here was this gorgeous woman asking me to her place to watch porn, not just any porn either, transsexual porn. “Sure, I’d love to. Just let me run back to my place and change and I’ll be back in fifteen.”
“Great, see you in fifteen minutes.”
I arrived back at Pandora’s box about ten minutes to ten o’clock wearing something more casual than the suit I had worn to work. I stood Pendik Ukraynalı Escort by the counter making conversation with Maggie for a few minutes before she retreated to the office to grab her things.
We stepped out of her car and walked to the door of her house. As we entered she asked, “What do you think about some pasta?”
“Sounds good to me, much better in fact than the burger and fries I was planning on,” I said. I helped her prepare the dinner and we chatted. She said that she had graduated from the same high school I did, only two years earlier. “I find that hard to believe,” I said, “I would have remembered a girl as beautiful as you for sure.”
“I’ve changed quite a bit since graduating, I was pretty awkward in high school. I doubt anyone remembers me.”
After dinner, we were both working on our second glass of wine when we turned on the movie. It was an awesome flick with an all-star cast featuring Vicki Richter, Gia Darling, Danielle Foxxx and Allanah Starr.
A few scenes had gone by when Maggie excused herself, “I’m just going to slip into something more comfortable.” She came back a moment later wearing a blue, low-cut negligee which came about halfway down her thighs.
Watching the movie had given me quite an erection. Maggie saw this and said, “Now what kind of hostess would I be if I didn’t take care of that?” She got down on her knees in front of me and began to unzip my pants, followed by the button, and soon she was sliding my slacks down revealing my boxers and the tent my erection created within them. She then removed my boxers with her teeth, biting them and dragging them down at an agonizingly slow pace. Once they were gone, she came back up and began teasing me with hot breaths on my cock and balls. She then licked from my ball sac up the underside of my shaft to the head, suddenly engulfing it. I felt the wet heat of her mouth as she continued down to the base of my nine inches, taking me in inch by inch until she had swallowed my entire manhood. She began slowly bobbing up and down on my shaft pulling back until only my glans remained in her mouth before continuing back down. Several times she paused at the tip to send her tongue in circles around the head of my cock. Each time she went a little faster: up, down, up, pause, down. She was good; this was quite possibly the best blowjob I’d ever had.
Soon I was approaching climax and told her so, but that only intensified her efforts. Within moments I was cumming, and she was taking it, all of it. Shot after shot of cum came out and she never released her grip on me, swallowing every drop that I could give her. Finally, I stopped cumming and my cock began to shrink again. Maggie let go of it and stood up. As I opened my eyes I saw her standing in front of me in that blue negligee. I followed her body downward until I saw that there was an impressive protrusion in the front of her lingerie.
My jaw dropped. It all came together now, but it still baffled me, after all this time I had never even suspected that Maggie could be transsexual. Seeing my reaction she said, “I thought you knew, why else would I have offered to invite you over to watch this movie?”
“I was not sure why you offered,” I said, “and I would have never have guessed, but why in the world would I turn down an invitation from a woman as gorgeous as yourself? I must say that this is a wonderful surprise, I am attracted to transsexuals but I have never been with one.”
“Well, I guess I am a lucky woman, I get to be your first.” She slid the straps off her shoulders Pendik Üniversiteli Escort and let the last of her clothing fall. For a moment it hung on to her cock before falling to the floor, revealing the most beautiful uncut seven inches I had ever seen. “Are you ready for this?”
“Absolutely. Come closer so I can taste it.” As she stepped forward, her cock came within inches of my face. I could see the head just peeking out of her foreskin, begging me to suck it. I reached out and pulled back the foreskin to reveal a lovely engorged head, which I quickly took in reveling in the warmth of it in my mouth. I breathed in the sweet and slightly musky scent of her, savoring every new sensation. As I began to take more of her into my mouth, Maggie released a slight moan, adding to my enthusiasm. Trying to imitate her technique, I slid down her cock slowly taking in inch after delicious inch. I tried to reach the base of her cock, but I was only able to manage about five inches before I had to stop as it hit the back of my throat. I began to slide back up her length until only the head remained in my mouth. I stopped there and began to encircle her head with my tongue as she had done to me. Her moaning increased and she began thrusting her pelvis slightly telling me I was doing the right thing. I began to speed up trying my best to repeat on her what had been so effective on me.
After about ten more minutes of this I felt her thrusting become less consistent and suddenly her cock began to convulse inside my mouth and I felt the first stream of her cum hit the back of my throat. It was salty, as I have heard it is, but it was also surprisingly sweet. Delicious. I did my best to keep it all in my mouth but some of it began to slip out and dribble down to my chin. I swallowed what I could, savoring every drop and sucking diligently to get out all I could. As her convulsions stopped and her cock began to shrink I let it go and looked up at Maggie.
“Oops, it looks like you dribbled,” she said, “let me help you.” She pulled me up and with her index finger recovered the lost cum and fed it to me. I took her finger and licked the cum off of it and swallowed the last bit of it.
“Thank you Maggie, that was delicious.”
After giving Maggie a blowjob, my own cock was rock hard again and ready for more. She looked down and remarked with feigned worry, “Oh, no it’s happened again. Perhaps we should take this to the bedroom so that I can take care of that properly.”
“You’ll get no argument from me, let’s go.” She led the way and I followed her down the hall watching her taut, round cheeks bobbing as she walked. As we entered her bedroom, she lay herself down on her king-size bed and beckoned me with one finger to join her. I did as I was told and joined her, leaning down to kiss her for the first time. Our lips met and immediately her tongue entered my mouth and found my own. We kissed passionately for what seemed like an eternity, lips pressing against lips, our tongues engaged in a battle neither intended to finish.
We finally released each other, our breathing labored from the greatest kiss either of us had ever experienced. I took her in with my eyes: her beautiful face, down her thin neck to her shapely, ample, breasts, over her toned stomach, to her penis, already beginning to grow again, down her smooth legs, and finally to her painted toenails; every inch of her perfect. I began to kiss her neck, trailing down, past her collarbone to her breasts. I took the right nipple in my mouth as I squeezed the breast, sucking on it, Pendik Vip Escort making it hard. I ran my tongue back and forth across it several times before switching to the left breast and repeating. Her breathing quickened and she whispered to me, “Fuck me, please.”
She reached for the nightstand and removed from the top drawer a condom and a tube of lubricant. She handed them to me and then turned over on her hands and knees and presented me the most perfect ass I had ever seen. I rolled the condom over my now raging erection and smeared lube liberally on the condom and her anus. I got behind her and placed the head of my cock at her entrance, pushing gently. Slowly I began to penetrate her, first just the head, then inch by inch I entered her until I was in to the hilt. She was tight, so I took my time with the first few thrusts, quickening slightly with each one. Then Maggie surprised me and said, “Fuck me hard!” At her request, I began pumping my cock deep inside her with hard quick thrusts. As I filled her up with each thrust, I felt my balls slap against hers, another new sensation I welcomed. After ten minutes of this amazing sex, she stopped me, “Pull out, I want to see you fucking me.” I pulled out and Maggie turned over on her back, her cock now sticking straight up, a thick drop of precum sitting on the tip. Before I resumed fucking her, I bent down to lick the precum off of her. It was even sweeter than her cum. Bringing my cock back to her anus, I slid it in, quicker than last time as our fucking had relaxed it. I once again started to fuck her hard, staring into those deep, dark eyes, giving her all I had. She began stroking her own cock in rhythm with my thrusts. Seeing her stroke herself while I fucked her brought me to the brink almost immediately.
“I’m almost there,” I told her.
“I want to taste you again,” she said, “I want you to cum in my mouth.” I pulled out, removed the condom and moved up the bed until my cock was within reach of her mouth. She took it and began sucking it with even more intensity than before. Within moments, I was cumming in her mouth again, and she was swallowing every drop just as before.
I removed my softening cock from her mouth and looked down toward hers and noticed that she had cum while she was sucking the last remnants from me. Her second load of the night had ended up all over her stomach and breasts. “I guess the oops is mine this time,” she said.
“Well then, I guess it’s my turn to clean it up.” I bent down and licked every last drop of her salty/sweet cum off of her breasts, her stomach, and her cock, loving the taste of it. For a few moments afterward we just lay there together, basking in the glow of the night’s activities.
Maggie was the first to break the contented silence. “So, Paul, were you serious when you said that you had no idea I was transsexual?” Maggie asked. “You really never would have guessed?”
“Never in a million years,” I said, “even knowing now I can see nothing other than your magnificent package that would suggest it.” Maggie smiled and blushed a little. “I did always wonder why you were working at Pandora’s Box instead of being an underwear model or something, but I guess most people wouldn’t be to comfortable seeing such a lovely bulge in a woman’s panties.”
“Well, I am certainly glad that you’re comfortable with it,” she said. “And since you are, if you would like to see me model some underwear for you, I would be glad to do it.”
“Any chance I can get to see that gorgeous body of yours,” I replied, “I’ll take it.”
“How about now?” she said, standing up and walking toward her closet. Moments later she emerged in another sexy negligee, this one shorter than the last, stopping around her bellybutton. As she sauntered back toward the bed, her half-erect penis swaying beautifully between her legs, I knew it was going to be a wonderful weekend…
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