Danny's Education

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Jem teaches Danny about role-reversal.
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Greymead
Greymead
80 Followers

"Damn it, Jem! I'm a doctor, not a sissy!"

Jemima chuckled, recognizing my weak attempt at humor as I tried to avoid the question. She was still holding the brief, lavender panties out to me. "C'mon, honey. Just do it this once for me, please?"

Her big eyes begged more eloquently than her voice, and, though I didn't care to let her know in case it made me any less a man, my cock was already stirring at the thought of playing this game with her.

"Tell you what," she continued, "I know you enjoy lesbian porn. What would you say if I make you up all pretty and you wear the panties and bra, and we can be lesbian lovers? Wouldn't you enjoy that?"

"Honey, I don't know where you got the idea I want to pretend to be a girl, but no." I sat on the bed in an effort to make the bulge of my incipient woody less noticeable, but it was too late. Her eyes were already focused on my crotch and her smile told me that she was certain that she was going to win my compliance.

"Tell me the truth, Danny, you are intrigued and aroused."

"No... yes," I mumbled, "but I don't want you to start thinking I'm some kind of sissy."

Her little smile widened. "Are you telling me that your masculinity is so easily compromised that doing this for me would make you less manly?"

While I struggled to find a logical answer to that that wouldn't make me seem totally moronic, I began to wonder how I had got myself to this impasse in the first place.

We had met in a film studies class at university. I was taken almost immediately by her open smile, not to mention her good looks and friendly personality. She didn't seem interested at first, but around the fourth or fifth week, when I asked if she wanted to go to a screening of an old movie in the student center, she had agreed. I hadn't check to see what was showing -- I think that was my first mistake. It was a restored print of Victor/Victoria, a musical made in the early eighties. The plot has a female character pretending to be a cross-dressing male, and there are plenty of shenanigans around the ideas of cross-dressing. To be frank, I probably would have taken Jemima to see it even had I known, but I am pretty sure it was the thing that first gave her the inkling of an idea that I might enjoy getting into drag.

"What did you think of the film, Dan?" She fixed me with a quizzical grin that I only now realized suggested she was after more than a simple answer.

"I liked it. It was funny, smart, and Julie Andrews really carried the concept of a man in woman's clothes so well that at moments, I forgot that she was playing a woman playing a man playing a woman. Did that sentence make sense?"

She squeezed my hand. "Yes. It did."

Some weeks later, she asked me if I would join her for a drink after class. It was not unusual for our crowd to drop by one of the local establishments for a little libation with our after class discussions, but it would be the first time we were alone there together. As I already mentioned, I had a crush on her from day one, so of course I agreed.

Shortly after we had snagged a two-top in a corner and ordered drinks, a petite woman walked into the bar. Jem (who had asked me to stop with the Jemima already) called out "Bobbi! Over here!" As the blonde came close, Jem turned to me. "This is Bobbi. We've been friends for years. Bobbi, this is Danny."

"Well hello, Danny! Jem has told me so much about you." Her voice was a pleasing contralto, considerably lower pitch than I would have expected from such a small woman.

"I hope that whatever she told you was, at least, not too awful."

Bobbi shared a quick glance with Jem and smiled. "Oh, not at all, honey! Quite the opposite, in fact."

After half an hour or so of small talk, conversation turned back to Jem and Bobbi. Apparently, they had been in high school together. "That was when Bobbi was still a boy, of course," Jem mentioned it so off-handedly that I almost missed it.

I looked at Bobbi again, trying to find the boy inside and failing.

"Didn't your Mommy tell you that it is not nice to stare?" Bobbi asked in a manner that suggested that she was highly amused.

"But you are a girl now?"

"Want to find out?"

"Actually..." I began, as much from curiosity as from horndog interest.

"Hands off, Bobbi," Jem warned. "I am marking territory here!"

Whoa! Up to this moment, I had not realized that her interest in me might be almost as strong as my interest in her. It surprised me nearly as much, how territorial her tone was, though in my pleasure at discovering her interest in me, I let that last part slip out of conscious thought.

After Bobbi left and we ordered another drink, Jem grinned at me. "What do you think of Bobbi? Isn't she beautiful?"

"Yes. Yes, she is beautiful. I would never have guessed she used to be male."

Jem leaned over the table and kissed my cheek as she put her hand on top of mine. "I'm feeling hungry," she admitted.

"Wanna go somewhere for dinner?"

"Not that kind of hungry. My place is only a block away." She fixed me with an inquiring smile.

I grinned my idiot grin and stood. We walked the block and a half to her place, a second floor walk-up. She was on me as soon as the door was closed behind us, clamping her arms around my shoulders and mashing her lips against mine. Her tongue stroked and probed at my lips and found entry.

This was a first for me. My tongue had been in the mouths of girls and women before, and sometimes theirs followed mine back into my own mouth, but no woman had ever taken the initiative so demandingly as Jem did that first time we kissed.

In short order, we were out of our clothes and on the bed. Pushing me onto my back, Jem straddled my hips and bent down to take a nipple in her mouth, biting gently at first and then harder until I squealed. Then, sucking hard on it, she took the other between her fingers and started rolling it between them, pinching.

No one had ever done these things to me before, and I was startled at how electric the sensations were and how they seemed to transmit directly to my cock, which was already hard at the promise of things to come, but which was quivering far more now than it had.

When her hand found and curled around my cock, I thought she was going to move lower and take it in her mouth, but instead, she raised up, positioned her wet and aromatic cunt above my mouth and licked my cock from that position.

Naturally, I pulled her down so that I could feast on that glorious twat, stroking it inside and out with brief occasional swipes across her turgid clit. Her groans of pleasure kept me focused on her even though part of me wanted to stop what I was doing to revel in the attention she was bringing to my cock. When I slowed, she did likewise in silent warning that if I didn't keep up my end of the deal, she would leave me hanging.

Realizing that my pleasure was going to depend on hers, I renewed by assault with increased vigor and was soon rewarded by her grinding her sloppy wet cunt against my face as her thrill found voice in a high-pitched squeal and scream.

As she recovered, her mouth engulfed my rampant prick again. I could not see, her whole body resting as it was on top of mine, but it felt to me as if she swallowed the length of it and began milking it with her tongue. I felt the warmth of a gathering ejaculation interrupted when something poked at my anus.

"What?" I complained.

"Shh. It's all right. Relax, honey." As she spoke, her finger wiggled into me. Then, licking my balls and then swallowing my cock again, she started sucking in earnest, her finger fucking in and out of my ass in counterpoint to her mouth. The jism warmed up again, hotter and larger than before and when it finally erupted, I could feel the heat of it draining from somewhere behind my balls, burning through my cock and into her sucking, swallowing mouth.

As soon as she swallowed the last feeble spurt, she turned and knelt over me as if for a kiss.

I didn't want to kiss her just then. I didn't want to taste my own cum, but she leaned down, captured my mouth with hers, opened mine with her tongue and pushed the whole load of cum into my mouth.

I sputtered, but she put her hand over my mouth. "Swallow, honey!"

Well, if she could, I suppose I could, too, I rationalized, and swallowed.

"Good boy!" she grinned and then kissed me again before turning back to place a kiss on my cock.

I had only a little experience with sex before I met Jem, not enough to know whether or not this was 'normal,' and in any case, I had always railed against the push to be normal. It felt good, and it was an eye-opening experience to find out that a woman could be such an enthusiastic partner in sex. After all, through high school and the stories we guys told each other, sex with a girl was something you kind of had to trick them into or something. We had never considered that females might enjoy it just as much. At any rate, her behavior was a good thing in my esteem. And, as I said, because I didn't know what 'normal' was, there was no way I would think it was abnormal. My only concern was to wonder if I had been 'good enough' that she might want a repeat performance.

"Did you like it when I stroked your prostate? You sure came a bunch!"

Startled out of my thoughts, I looked at her. "Prostate?"

"You know, when I stuck my finger in you. While I was sliding it in and out, I was also tickling your prostate."

"Oh..." I had heard the word before and was trying to remember what it was.

"It's a little gland up behind your balls. Did you like that?"

"Well, I don't know about having your finger in me, but I sure did cum good!"

She smiled. "I think you are going to come to love it, darling."

Then, to complicate my worrying whether liking something in my ass would make me gay, I began to wonder if her use of 'honey' and 'darling' was just her southern way of talking or if she figured I was her boyfriend or what. I was a complicated, mixed-up kid, for certain.

In the next several weeks, I spent a lot of time at her place after classes, and she spent a lot of time introducing me to the kind of things she liked. One time, Bobbi was there when we got to the apartment.

"Jem! Danny! I let myself in to wait. I hope you don't mind, Jem. Do you want your key back now that..." She shot a signifying glance in my direction.

Jem smiled. "Sweetie, you hang on to that, okay?"

Anyway, some kind of signal must have passed between them because Bobbi rose from the sofa where she had been sitting and hugged me hello. I hugged her back, and when she didn't let go of me, looked at Jem. She was smiling. As I was processing this, Bobbi took my earlobe between her teeth and bit it softly. I did not believe I could go from soft to rock so suddenly!

When she felt the probing of my cock against her belly, she reached down to cup it through my trousers.

"Oh, Danny! It feels so big and hard. Can I see?" and without waiting, knelt and began unzipping me. I looked a Jem again to gauge her reaction, fully expecting to see anger, but she signaled me that it was okay, that I should let Bobbi do what she was doing. Not being inclined to argue, I watched Bobbi open my fly, reach in, and fish out my cock. She was right, it was big and hard and the knob was already shining with precum. She looked up at me and grinned. "I am going to make you feel so good and you are going to give me all your sweet cum, sweetheart!"

Speechless, I watched as she licked around the knob, then, raising it, licked my balls before she dragged her tongue up its length and, finally, engulfed the knob in her mouth, suctioning so hard I thought she would suck my balls out through my cock.

I was almost ready to pull her off, it was starting to hurt, when she suddenly bent forward and engulfed the length. I wouldn't have believed this small woman could swallow the whole thing, but I saw it with my own eyes and felt the constriction of her throat as she swallowed repeatedly, milking me.

She gasped as she came up for air, then began fucking my cock with her mouth as she rolled my balls in her hand. It was probably less than a minute before I came, but it felt like an eternity in cock-sucking heaven.

As she swallowed my cum and then released my cock to wipe her lips, she smiled up at me.

It can be funny the way unexpected thoughts can cross your mind at an inappropriate moment, but as I looked down into her eyes, I wondered whether it would have been even more spectacular had she fingered my prostate as Jem had. Needless to say, I said nothing about that thought, but instead thanked Bobbi profusely for her gift.

"Kiss him, Bobbi," Jem said.

Bobbi stood and leaned her head back so that I could kiss her, and I did. Any feelings I might have harbored about tasting my own cum had been long banished. Instead, I enjoyed the mingled flavors of my cum and Bobbi's saliva.

"Um. Well." I really didn't know what to say. Thank you seemed totally insufficient, but saying nothing was worse. "That was unexpected..."

Bobbi smiled up at me. "Thank you, Danny. I enjoyed that!" She seemed amused at my inability to express my thoughts. "Did you like it? I think yes, because you sure seemed to get into it."

"It was wonderful, Bobbi," I tried. It still seemed excruciatingly incomplete.

"I am glad you like each other," Jem smiled. "I think you are a lot like each other."

I couldn't see the similarity, but, drained and happy, I was not going to argue with her. Besides, she was pulling her dress over her head, which was distracting me from paying close attention to anything else.

As she pulled the hem up to her waist, I appreciated the fact that she had not been wearing panties. The stockings and suspender were a surprise -- I don't think I had ever seen those outside of vintage porn and old Sears catalogues. The black panels framed the red thatch of her cunt as if to draw attention to it, which it certainly did.

Her bra, as it turned out, matched the suspender, with sheer cups, through which her stiff nipples and wide, dark areola could be glimpsed, completed the picture.

Bobbi moved to embrace her, and I was treated to a hot, wet girl-girl kiss which got my drained pecker stirring again.

Jem unfastened Bobbi's skirt, and Bobbi stepped out of it when it fell to the floor.

Bobbi was wearing panties that seemed to share some qualities with the girdle my mother used to wear when I was a child. Her bra was a wisp of a thing which seemed designed to decorate rather than support her small breasts.

Jem put her hands on Bobbi's shoulders and encouraged her to turn around, which Bobbi did with a smile for me over her shoulder. As Jem wiggled the tight panties down Bobbi's legs, Bobbi bent down and placed her hands on the chair that stood by Jem's bed. Jem looked at me. "Are you ready, hon?"

I was not sure what was expected of me until she looked significantly at my cock, which, contrary to my expectations, was already standing up again. Jem smiled. "Yes, I see you are. Come here and fuck this pretty ass!"

I had never fucked anyone's ass before. As I mentioned, I hadn't a great deal of experience, but I was hard, Bobbi's as was pretty, and I put a hand on each of her hips and guided my cock toward her anus.

"Wait," Jem giggled. "You're going to want some of this." She opened a jar and scooped out some slippery looking goo and spread it on Bobbi's anus, probing with her finger to get some inside, and wrapped her hand around my straining cock, spreading the stuff on me, too. "Okay, honey. Now." She held the tip of my cock to the pucker of Bobbi's anus and, with her other hand, pushed my ass forward. Taking the hint, I eased into the tightness, thrilling to the tight constriction as it engulfed the head of my cock.

Bobbi groaned, and I stopped, concerned that maybe I was hurting her. "Don't stop! Give me that beautiful cock, boy!"

As I pushed in, Jem slid between my legs and Bobbi's, then sat up and wrapped her lips around the cock I had not noticed before, lost as I was in the immediacy of unfolding events.

We had Bobbi sandwiched between my cock and Jem's mouth. Bobbi pushed back against me as I drove deep into her ass, then thrust forward into Jem's mouth, the suction on my cock pulling me with her.

I pushed her hips away from myself only the head of my cock was still buried, then took another deep thrust, causing Bobbi's cock to slide deep into Jem's throat.

Almost as soon as we had a rhythm established, Bobbi came. I was still not close, having cum only minutes earlier, and as I continued to fuck in and out of her, Bobbi fucked back against me.

Jem wiggled out from under us and knelt by Bobbi's head to kiss her deeply. I think she was feeding Bobbi her cum as she had fed me my own that first time. The thought of that triggered my cum, and we ended up collapsed on the deep rug on Jem's floor without the energy even to climb onto the bed.

That had been my first threesome, but it was not going to be my last, but let's not get there too soon. We still need to get back to the event with which I opened my story.

Jem held the skimpy panties out to me again. "I know you can't be worried that you might be gay. You didn't think about that when you fucked Bobbi, did you? Of course not. There was nothing unnatural about that." Her smile was so sweet. "I think you want to, but something in you is afraid. Am I right?"

"Okay. When I met Bobbi, he was afraid of being thought a sissy. But deep inside, there was a girl who desperately wanted to be out in the world. I can't tell you how I could tell. I don't know myself how I knew, but I did. But you are different. I don't think you want to be a girl. I know that you want to experience sexual adventure in every way possible, and this kind of role-play is something I know you want. I have been watching the way your beautiful cock twitches at the thought. So drop those trousers right now, and put on these panties. I promise, it won't go outside this apartment if you don't wish it to."

Actually, that did address one of my concerns, that somehow this was going to publicly humiliate me and brand me for life. That was the moment I began to soften.

There was also something commanding and compelling about her voice when she said 'right now' that made me want to comply. No, comply is the wrong word. It made me want to obey. I stood, unbuckled my belt and skinned trousers and shorts, realizing belatedly that my shoes were still on. I sat and removed my shoes and socks, pulled my trousers the rest of the way off and put them on the bed as I stood again to take the proffered panties.

They seemed fragile in my hands. The fabric was light with a floral pattern in the lace of the front panel. I stepped into them and pulled them up over my ass. Jem smiled and stood in front of me, adjusting the waistband and patting my turgid cock through the lace. I admit, it made me feel just a little bit dizzy.

"Sit here," Jem indicated the little chair in front of her vanity. Turning my back to the mirror, she began doing things with powders and brushes, then began to work around my eyes with different brushes.

There was something about sitting there, letting her do these things that sent my mind into a sort of hypnotic state that was so warm and pleasant that by the time she was finished putting lipstick on me, doing some final touch-up and told me to turn around to look in the mirror, it felt like waking up.

I was reluctant to look. I had seen pictures of men dressed as women, and many of them looked just like that. Men dressed in women's clothes.

"Go ahead, honey, have a look," There was pride in her voice, and I had already learned that I would always eventually do as she asked, so I turned to look.

I was astonished. I did not look like a man trying to look like a woman. Well, yes, there was some hair on my flat chest, but my face was so perfect, so pretty!

Greymead
Greymead
80 Followers
12