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Author's Note: (a) This is a pilot story. Tell me if you liked the idea, and I will continue the story. (b) I would love to receive ideas and suggestions for a sequel. This may not be reflected in the next chapter, but it will affect the rest of the story. (c) Please note that this is a bisexual story, if that's not your thing - don't read it.
What Am I?
I was born as the third boy after two boys. My father is a successful lawyer, and my mother is an insurance agent who works from home. Until the age of 3, my mother raised me at home. At the age of 3, I started going to kindergarten, and then to school. Like any other child.
But I wasn't like all the other kids. I noticed it at a young age and tried to hide it. When my breasts grew, I was sure it was excess fat in the chest area, so I trained my chest muscles for hours in the hope that the fat would break down. The "fat" didn't break down, but my tennis shots became stronger.
When I was 18, I decided I needed medical advice, so I went to my family doctor, Dr. Baldwin. After a thorough physical examination, he explained to me what a hermaphrodite is, and told me that this is what I am -- both a boy and a girl. Throughout his explanation, I was thoughtful, trying to understand what I was hearing.
Finally, I asked, "Does this mean I can get pregnant? Have children?"
"Basically yes," the doctor replied with a smile, "you have a uterus. But more tests need to be done."
"And be a father?"
"Probably yes," the esteemed doctor replied, feeling my balls, "you see? You have scrotum under your penis."
"Look," Dr. Baldwin added, "you need to undergo a long series of tests that cost a lot of money. I'll refer you to my colleague, whose name is Dr. Reese and she's a research physician at the University Hospital. She'll be able to answer all your questions better than I can and she'll also be able to get you funding for all these tests."
"But I don't want to be a woman," I said. "I'm a boy."
"I suppose you could be a man," he said. "And you could also be a woman. That's for you to decide."
"A woman with a penis?" I asked.
"If you decide you want to be a woman, it will be possible to operate and remove all the male genitalia."
"But everyone knows I'm a boy," I protested.
"That's true. That will be a hurdle we will have to deal with in due course. But first we need to be sure that your reproductive organs are functioning well, only then can you make an informed decision."
My mother was the closest person to me, I was what they call a "mommy's baby," so that very day I told her about the visit to Dr. Baldwin and asked her, "Since when do you know that?"
"Since you were born, honey, they told me that in the hospital."
"Does Dad know too?" I asked. My relationship with my dad wasn't very close.
"No," Mom replied. "I thought it was something that when you grow up, you will decide for yourself who to tell and how much."
My sexuality had not yet matured, and my thoughts wavered, once considering what would happen if I'll want to be a girl and once if I'll want to be a boy. Would boys accept me as a girl and would girls want me as a boy.
"Mom," I asked one day, "if I decide I want to be a boy, what kind of girl would want to marry a boy who has breasts and gets his period once a month?"
"There are many women who enjoy both a female and a male body," she replied. "They will love you. You can satisfy all their desires in one body."
"Can't they operate and remove all my female organs?" I asked.
"I suppose they can, but we'll have to get medical advice about that. Did you go to that doctor that Dr. Baldwin recommended?"
The thought of having to expose my genitals to a female-doctor froze my blood, and I was in no hurry to make an appointment with Dr. Reese.
"Mom," I asked my mother, "do girls enjoy sex too?"
"Of course," she replied. "There's a little bump at the front of your slit, like a small pea, that if you touch it, it sends pleasant shivers down your spine."
By the end of high school, I was the only boy in my class who hadn't grown facial hair yet. The boys weren't making fun of me yet, but I decided I couldn't put off figuring out my sexuality any longer. So I made an appointment with Dr. Reese.
It turned out that Dr. Reese was a young, beautiful, smiling woman with prominent breasts that were visible even through her doctor's robe. She had large blue eyes and hair that ranged from red to blonde and was rolled up on top of her head. As soon as I entered her, I began to feel my erection rising.
"Michelle Hagen," she said without greeting. "I was wondering when I would get to meet you?"
I was surprised. "Do you know who I am?"
"Of course. Dr. Baldwin told me about you. I have to admit that even though I learned about the condition you have, I have never encountered it. I'm really glad you came."
"Maybe I should..." I began, not knowing how to continue without offending her.
"... see a more experienced doctor?" She finished my sentence. I nodded.
"Don't worry, my dear. We are going on a long journey, you and I, and along the way you will see many very professional doctors. Those who specialize in one field or another. But I'll accompany you throughout the journey. Now please undress."
She said "undress"? Just like that? Without any small talk? My knees were shaking.
She smiled at me with a mocking smile. "Relax, I'm not trying to rape you. But I have to see all your genitals," she paused for a moment and smiled at me, "and it turns out you have quite a few."
I undressed with shaking hands and stood in front of her. She stood up and came closer to me. My cock got even harder. Embarrassing.
"Mmm," she said, "nice genitalia you have there. I'm sure boys, who are totally boys, are quite jealous of you." And without blinking she took it in her palm.
I gasped and she let go of my cock. "Okay," she said, "first thing first." She gently squeezed my breasts, which were no longer very small, and added, "Pretty nice breasts too. And the tissue inside feels good. There's a good chance these are functioning breasts."
She continued massaging my breasts and then asked, "What do you feel when I do this?"
I swallowed hard and said, "Chills."
She nodded and smiled, then gently slapped my nipples with the tip of her finger. "And now?"
The current her touch sent through my body made my legs collapse and she supported me and propped me up on the treatment bed. "You don't have to answer," she grinned. "Well, your chest is perfectly healthy. Let's move on to the lower part. Lie down on the bed."
I lay down and she stroked my cock again. "Now?"
"I..." I began, "Oh, I..."
"I understand," she said. "Intimate question: Have you ever masturbated with your penis?"
I couldn't find my voice and just nodded my head. "And did you enjoy it? Did you ejaculate?"
I nodded again.
"That's good," she said.
She moved to my scrotum and stroked it, first between the balls and then the ball itself. "What does that make you feel?"
I found my voice and replied, "Wanting you to never stop." Then I realized what I had said and blushed. She burst into laughter and said, "Nice answer!"
From there she moved to my pussy. She grabbed my lips and parted them, ran a finger along the inside, then found the entrance to my vagina and pushed the tip of her finger inside. The shivers that ran through my flesh were completely new to me. I felt my anus contract forcefully, and I closed my eyes and gasped quickly.
"I guess I don't need to ask how you feel," she giggled. "I think your vulva is fine too. Now I'm going to touch you in a very sensitive spot. Do you know your clitoris?"
I nodded silently.
"Have you ever masturbated with it?"
I swallowed again and replied, "No, but I touched it."
She gently touched my clit, making me fold.
"Your nervous system is perfectly normal. Okay, lie on your left side."
I turned around and she said, "The next test will be very unpleasant, but it's necessary."
This time she put on a glove and scooped up some Vaseline with her finger. With one hand she spread my butts apart and then... shit, shit, shit, she pushed a finger deep into my asshole. It didn't really hurt, but it was very unpleasant, and I moaned loudly.
"I'm really sorry," she said. "I have to poke around in there. It won't take long."
Finally, she pressed something inside and asked me, "How does that feel?"
"I don't know," I replied. "Very sensitive. Too sensitive."
"Correct answer," she said. She scooped up some paper towels and placed them in my hand. "Clean yourself up, get dressed, and let's talk."
She then asked me about my period, my sexual attraction, and all sorts of other embarrassing questions. Then she asked the most embarrassing question of all, "Have you ever had sex? With a man or a woman?"
"No," I replied. "I haven't even undressed in front of a man or a woman."
"That's very understandable," she reassured me. "Well, we're going to need to do some tests -- a semen count, a CT scan of the uterus, an ultrasound of the testicles and breasts, and I also want you to see a sexologist, a psychologist who specializes in sexuality. Because of the rarity of your physical structure, and the challenge it presents, I can arrange a funding to come from a research foundation, so all of these tests won't cost you a cent."
She gave me a business card with her cell phone number on the back, and said, " I'm going to refer you to all sorts of professional doctors who will send you for all sorts of tests. I've also written down my personal number for you, in case you can't make it." She waited a few seconds before winking at me and adding with a grin, "And this isn't for setting up a date."
Even though I blushed until my face was burning, I said, "Then there will be a date in the end."
She laughed again and said, "You never know what happens in the end."
*****
Well, it was a long road that involved all kinds of doctors -- urologist, endocrinologist, gynecologist and all sorts of other specialties that I've forgotten. They sent me for all kinds of tests. I did all the tests, and she accompanied me the whole way, but there was no date. At our last meeting, about a week before I started college, she said, "There is no reason for you not to be a woman and get pregnant, and there is no reason for you not to be a man and get a woman pregnant. One day you will be able to decide what you want to be, a man or a woman, or both. Physiologically, you are fit to be both. At this point, I don't have much to add. After you have sex, contact me again and we will talk again. Have you met Dr. Scott? The sexologist?"
I answered no. To be honest, I was quite scared to see a psychologist.
"I recommend that you do not put it off any longer. The psychological aspect is really critical for you at this point."
And that was the end of it. No date.
*****
It turned out that the sexologist was actually a female, and I met with her in her university office. She wasn't wearing a doctor's robe, but a dress that covered her knees. She had a slim, curvy figure and a round chest, on which a pearl necklace rested. Her chestnut-colored hair was tied in a ponytail that fell down her back. Her eyes were long and green like cats'.
She greeted me at the entrance to her office with a cold face, shook my hand, led me to a very uncomfortable chair and sat down opposite me in a comfortable armchair. Her face was smooth and frozen like a porcelain doll. I sat down, and she crossed her long legs and stared at me for a long time. I looked away from her gaze and stared at her long marble neck.
Finally she asked, "Why did you come to me?"
I had an answer ready for that. "Because Dr. Reese sent me."
No emotion crossed her face, not a smile or an expression of impatience. "And why did Dr. Reese send you?"
"Because I'm hermaphrodite and my sexual identity is not entirely clear to me."
She stared at me for a long time again and then said, "Which do you feel more like -- a boy or a girl?"
"I'm used to feeling like a boy," I said. "I've been a boy all my life."
"That's not what I asked," she said. From the moment I sat down across from her, she didn't move, and with her porcelain face, she looked like a talking statue.
"I feel like a boy, but I'm not sure if it's because I'm used to being a boy." This time she was satisfied.
And so it went on. Questions and more questions. Every now and then she made a note for herself, but most of the time she was completely frozen. Even though she was very sexy, the coldness that flowed from her eyes suffocated my cock, which was contracted and didn't dare to move. But that night I fantasized about her. I imagined myself using her freely as if she were a sex doll.
In the next session, she asked me about my sexual fantasies, forcing me to describe in detail the girlfriend I would like to have sex with. Then, she asked me to describe the boyfriend I would want to have sex with. I didn't know who to decide on, I hesitated, and finally gave her a description of Jerry, even though he was the last person I would want to get into bed with.
I couldn't fool her out. "When you described Lauren, you gave a lot of details, some of them very intimate. About Jerry, you barely gave any details."
After two more sessions, she said to me, "Your sexual identity seems pretty clear. Do you have any doubts about that?"
The truth is, I only had them sometimes. Most of the time I felt like a man, but more than once I thought about what it would be like to be a woman, and the doubts always centered around the sexual issue.
"Sometimes I fantasize about a dick penetrating my vagina," I said.
This was the first time there was a response, although I'm not sure if the content or the language prompted the response.
"Do you also know who this organ belongs to?"
"I don't imagine the man, just the dick."
"In fantasies, and also in dreams, we often don't see the character, but we know his identity."
"I don't know who it is," I replied, and she stared at me for a long time again.
Then she asked, "Have you ever masturbated?"
"Many times."
"With the dick?" It seemed that vulgar language was no stranger to her, "Or with the clitoris?"
"Only with the dick."
"Have you tried masturbating with your clitoris?"
"I've touched it a few times, but I've never masturbated with it. It's very sensitive."
"Okay," she said, "I'll teach you how to masturbate with the clitoris. Please take off your pants and underwear."
I froze in place, not daring to move. Did I understand her correctly? Am I supposed to expose myself to her?
She stared at me and raised an eyebrow. "Do you need help with this?" she asked sarcastically.
"No, no," I stammered, "I... I wasn't sure I understood correctly."
"You got it right. Get undressed."
I undressed, and after she stared at my cock, she instructed me, "Sit in front of me and spread your legs. You might find it more comfortable if you put one foot on the seat."
"Now," she said, "spread the labia with one hand, and run a finger of the other hand along the slit, from the back to the front."
I was shaking so much that it took me a few tries to find my clit. "Very good," she said. "Now run your finger around it without touching it."
I tried, but my hands were shaking, and I kept touching my clit, and every touch of my clit made me jump.
"You're not spreading your labia properly," she said. "Try pulling up."
It didn't work.
Then she did something that made my balls contract violently, and I almost cum on the spot. She spread her legs and pulled back the hem of her skirt. The sight of her beautiful, slender legs, locked in high heels, spread in front of me made my cock stretch painfully. She wasn't wearing underwear, and I saw her magnificent cunt. Her lips were smooth, plump, and close together. She reached for her slit, parted her lips with her fingers, and pulled the slit toward her stomach. The red interior of her cunt was exposed to me, wet and shiny. I immediately saw her clit, and it was red, moist, hard, and very prominent. A clear drop of pre-cum emerged from the tip of my cock.
She ran a finger around her clit, a distance away. "This is how I want you to do it," she said.
The trembling in my palms was uncontrollable. I couldn't even part my lips. She pressed her legs together and threw the hem of her skirt over them. Then she stood up and returned with a shaving brush.
For the first time since I'd met her, she spoke in a soothing tone. "It's okay. I guess you're not in a comfortable position to do this right now. Try it again at home."
She showed me the shaving brush and said, "You know what this is? You can buy it at any toiletry store. It shouldn't cost more than a few dollars."
She handed me the brush and said, "Gently run the brush along the slit and then focus on your clitoris, as if you were sweeping it."
I did as she said and the shivers that gripped me sent me skyward. I closed my eyes and gave in to the sensation. I think she said something, but I didn't hear. I kept going, until I felt her hand on mine. She pulled the brush out of my hand and said, "You're not here to masturbate. That you'll do at home."
That same day, on the way home, I bought a shaving brush, and that night I had a crazy orgasm in my clit, something much stronger and much more shaking than any orgasm I'd ever had with my dick. The sight of her beautiful legs, in high heels, spread in front of me, wouldn't leave me, and that day I also tried, for the first time, to wear my mother's dress. I don't know if I looked very feminine, I think I did, but I definitely became aware that my legs were beautiful, and for an hour I tried to walk around my room in high heels.
At our next meeting I told her about the orgasm I had, and she asked, "And...? Did it make you think about men?"
"Actually, it didn't," I replied. "But it made me think more about sex with men."
One day, she got up and came back with a pretty thin dildo. I've seen something like that in porn movies, only they were much bigger. She handed me the dildo and said, "There's one more thing I'd like you to try. It's called a dildo. It's an expensive thing, so I don't think you should buy one until you're sure it's good for you. In the meantime, you can use mine. Do you know how to find the entrance to your vagina?"
I nodded silently, and she continued. "I assume you've seen this toy, or something like it, in porn movies." I nodded again. "Okay, then try using this dildo, without touching your clitoris. I emphasize, without touching your clitoris, and then tell me what you experienced."
I nodded silently again. I couldn't find my voice. "Keep in mind," she added, "that you're a virgin, so the first time you do it, you might bleed a little. Don't panic. I think the first time you do it, you should try it in the bathtub."
That day, and the days that followed, I tried the dildo. It wasn't like the shaving brush on my clit, but it was definitely enjoyable. A different kind of pleasure. Every time I pulled the dildo out of me, I felt an emptiness inside me, which made me want to put it back in...
*****
I am very sociable and have a wide build. In high school we were a tight-knit group of guys and girls. By the time we graduated, none of them were virgins anymore, except for me. I never tried to date any of the girls, and although we were good friends, none of them ever tried to date me.
A few days before college started, we all got together for a farewell party. They went on to the same college together, while I got accepted to a more prestigious college on a tennis scholarship. At that meeting, the subject of sex came up. Each of them told about their first time, and when they came up to me, I said in a joking voice, "You know you're not allowed to have sex before you're 18, right? It's the law. So I'm not going to admit to a crime in front of so many witnesses."
Everyone burst out laughing.
Jerry leaned closer to Kate and said, "You hear that, Katie? We're criminals."
"When are you going to be 18?" one of the girls asked.
"In November," I lied. Of course I was already 18.
"Shit," she said, "that's a long time to wait for a story."
They laughed some more and moved on to someone else.
The noise from our table must have drawn attention from the tables around us, because one of my close friends, Lauren, approached me and whispered, "Michelle, there's someone here who's really into you." She pointed to a brunette, about 30 or more, with a sweet face and a hot body, who was sitting next to a young man.
"I already have a girlfriend," I lied again, "and it looks like she has a boyfriend too, maybe even a husband."
"Let her decide," Lauren grinned. "Go to the bathroom. If she's interested in you, she'll come after you. Just get her phone number and come back."
My legs were shaking. An unfamiliar woman was new territory for me. "Leave it," I blurted out.
Lauren exchanged a look with her and got up to go to the bathroom. As Lauren had predicted, a minute later the brunette also got up and went to the bathroom. After a few minutes Lauren returned and pushed a napkin with a phone number into my hand.
"You're welcome," she said.
The very next day I called her. She answered on the first ring, "Jenny."
"Hi," I said excitedly, "We met at the restaurant yesterday."
"Oh, hi," she said. "I was hoping you'd call."
"Want to meet for coffee today?"
But she was much more direct. "Why don't you come over to my place. I have all kinds of coffee."
I felt my legs shaking and hurried to sit down. I took a deep breath and said, "We'd better talk first. There's something I need to tell you about myself."
"Tell me now," she said. "Let's see if you can scare me."
I wasn't sure how she would react if she found out I was hermaphrodite, so I opted for a soft lie that might not put her off. "I'm a tranny," I blurted out.
She didn't panic. "Even better. Come to me." She gave me her address and hung up. I hadn't thought it would be so easy and my whole body was shaking with anticipation. A few minutes later I ran to the bathroom to masturbate.
*****
As soon as I entered her house, she pinned me against a wall and kissed me hard. Our tongues played happily inside my mouth, and my legs were about to collapse. She pulled away from me, surveyed me, and said, "Oh my God, you're so beautiful." I don't think I'm beautiful, but if she thinks so, then who am I to contradict her?
She seemed to be getting ready for me. Her long black hair was still wet from the shower and pulled back into a high ponytail. She had subtle makeup on and was wearing a push-up bra. She wore short shorts and a low-cut tank top that proudly displayed her brown breasts. Her skin was smooth, and her eyes were blue-green hue. Probably a mix of African American, or Indian, and Caucasian. She pulled back further and said, "I have many types of coffee. What do you prefer?"
She made coffee for the two of us, we sat down in her little living room, and she said, "I just got back from soccer practice."
That explained her athletic body and her flowing movements. Her gaze scanned me again and she asked, "Your breasts, are they real?"
"Absolutely," I said.
"Operated?"
"No," I replied.
"So... hormones."
I didn't answer, I just nodded. Damn it, I'm going to fuck this chick, this is no time for modesty. So, I plucked up the courage and added, "Want to see it?"
She seemed embarrassed by my directness but nodded.
I took off my T-shirt and unbuttoned my bra. Her gaze fixed on my full, erect breasts and she whispered, "Oh my God." Then, "Can I touch?"
"Of course," I replied.
She gently caressed one breast and then the other, kneading it a little, then playing with my nipples a little. A shiver ran through me, and she pulled back.
She licked her lips and muttered, "God, where did you come from?"
"The Holy Spirit sent me," I chuckled, "Or maybe it was the Satan? I'm not sure."
"Remind me to send a goat to the Satan," she laughed.
"The man you were with yesterday..." I said.
"Just a lousy date," she said. Then she took a deep breath and quickly asked the question that must have been nagging her all along, "I thought you guys saw yourselves as women and preferred men."
"I'm Bi," I said. "But I prefer women."
"Formally, I'm Bi too," she said. "I've had quite a few relationships with women, but I prefer men, and your beauty is just the way I like it."
"You're very beautiful too," I said. That wasn't true. She wasn't very pretty, but she had a nice, sweet face, and the expression on her face reminded me of my mother. The ultimate woman to lose your virginity with.
I felt uncomfortable getting dressed again, so I sat there without my shirt and bra on. Her gaze wandered from my face to my chest and back again. She licked her lips again.
"Do you really have a dick?" she asked. "You look like a woman."
What the hell, I thought, and said, "Want to see it?"
She licked her lips again and nodded silently. I stood up and pulled down my pants and underwear. My dick was bouncing out of them, taut and hard. "Oh my god," she said, "Holy shit." And without asking permission she reached over and grabbed it. She leaned over and licked the tip of it, then under the glans, then the tip again to clean up the pre-cum. Finally, she just took it into her mouth and deep into her throat. She didn't suck it, just raised and lowered her head on it.
"Don't cum," she said suddenly, "I want you inside me."
"Don't worry," I replied. "Even if I do, it'll get hard again, and then again."
She lowered her head back onto my cock and licked it inside her mouth. I don't know if she was a good sucker, but I was so horny that I quickly started moaning. "Fuck... fuck... Jenny..."
She kept raising and lowering her head on my shaft, and I felt the orgasm rising from my balls in a strong stream. "Oh, Jenny," I moaned, placing both palms on her head, "Jenny, I think I'm cumming."
She didn't stop or even slow down and within a few moments I came with a loud moan, "Jenny... oh my god... Jenny...."
She continued to lick me until the flow of my sperm had completely stopped and then straightened up in place.
"I'm sorry for being so impudent," she said. "I couldn't resist. You have a very nice cock, besides your gorgeous breasts and your face that makes me wet just looking at you. Want to marry me?"
I laughed and said, "Let's find a priest." She laughed too and then fell silent, embarrassing me.
"It seems you have nice breasts too," I said, trying to break the silence.
"Thanks," she said and then, as if to repay me, "Want to see them?"
"Yes," I said, "but I'd like to be the one to expose them."
She stood up and I stood in front of her. I gently caressed the exposed part of her chest, then removed her tank top and bra. Her breasts were heavy and full, with only a slight droop. Her nipples were dark red and thick and the areola around them was wide and fleshy. I leaned down and took one nipple into my mouth, playing with it with my tongue. She trembled and stroked my head. I squeezed her soft breast, and a soft moan escaped her lips.
"Do you want to finish your coffee?" she asked.
"There's something I want more," I replied.
She smiled, took my hand in hers, and said, "Come."
She dragged me into her bedroom, where two scented candles were already burning. We stood by the bed and she put her arms around my waist. I threw her down on the bed, pulled down her shorts, and gave her head. I'd never been in bed with a man or a woman, but Literotica has a category called How to, and there I once read about how to give head. Several porn sites also have a category like that, with videos that demonstrate step-by-step how to do it. I grabbed her lower lips and spread them apart, then licked the inside of her cunt with long, end-to-end licks. At the same time, I gently pinched her lips, point by point, starting from the back and almost to her clit.
It turned out that she was quite the screamer, and she really loved Jesus, because she kept screaming, "Jesus... Sweet Jesus... Jesus, come to me..." Maybe she was the fucking Maria. According to one recommendation, I didn't touch her clit until she put both of her hands on my head and held me against her. I bit her clit gently with my lips, then sucked it. Her whole body trembled, and she screamed for Jesus to fuck her.
When she cummed, she grabbed me, pulled me to the bed, and attacked my cock. It was unnecessary, because it was already red and hard. When she realized this, she mounted me and fucked me, moving her hips rapidly in all directions.
"God," I thought to myself, "I'm fucking. I'm finally a man."
She was wild and kept rolling, sometimes she was on top of me, sometimes I was on top of her. Until she came. I continued to fuck her in short strokes while I was on top of her. She recovered quickly--an athlete, wasn't she?--and threw me onto the bed. I'm also an athlete and have strong arm muscles, so I grabbed her and flipped her onto her stomach and entered her again, lying on her back and kissing her neck. This lady got my blood pressure up. Soccer player or not, her skin was smooth, warm, and soft, and I couldn't stop caressing and kissing her.
She kept moving, trying to free herself from my weight. Her moans got louder and louder until she screamed, "Stop teasing me, you bastard, and start fucking."
I lifted myself off her back to sit on my knees and continued to fuck her with slow, hard strokes, kneading her round buns and massaging the muscles in her asshole. Her moans got louder, and she screamed again, "Jesus, get in there and that's it."
I pulled myself out of her and aimed my rod at her asshole, which opened up and welcomed my shaft. I lay on top of her again, only this time I fucked her hard, tearing her asshole apart. She trembled all over and quickly went back to calling out to Jesus. I felt like I couldn't take it anymore and to buy time, I pulled myself out of her ass and stuck my stick back in her vagina. I waited to see if the orgasm would be stronger than those I got from my hand, and I wasn't disappointed. It only took a few more minutes for her to cum screaming. A short second later I cummed too, hard, with my whole body shaking.
We lay side by side exhausted, as she caressed my breasts and I hers, and then she lowered her head towards my cock. I wasn't concentrating, probably because I was in the clouds, otherwise I would have stopped her, or pressed my hips together. But I didn't. She grabbed my dick, massaging the root of it and sucking my balls. And then it happened...
She tried to press on the root of the penis, but her fingers sank into my flesh, deep into my cunt. She was startled and jumped back. "What the hell..." she cried. "Are you hurt? You have a real hole there!" Then she caught sight of it, recognized what she was seeing, and turned completely pale. "Oh my God, that's not a wound. You have a cunt." She said and backed away.
She tried to touch my lips with her fingertips, as if she were afraid of getting burned. "You have a cunt," she said again. "How can that be?" Then an idea came to her mind, "Surgery?"
There was no point in lying to her again. "I'm not really a tranny," I said. "I'm hermaphrodite. I was born that way. With a cock, a cunt, and breasts. No hormones, no surgery."
She flinched, her eyes boring a hole in my face. "There's no such thing," she stated. "You really are of the devil. The Satan sent you."
I burst out laughing uncontrollably. "God," I said, "stop talking nonsense. I'm just a hermaphrodite. There is such a thing."
She touched my lips again with her fingertips. I parted my lips for her, and she saw my shining pearl. Her lips moved silently, and I said, "Touch it. It's very aroused right now."
She touched it with the tip of her finger and immediately pulled back. Her gaze locked on my face, and she asked, "Do you also have..." She couldn't finish the question, so I finished it for her, "A hole? Yes." I pulled my lips back and revealed the entrance to my vagina to her. She closed her eyes tightly and opened them again.
"You're not dreaming," I said. "I'm completely real, and I'm completely human. I was born this way."
Her hands shook uncontrollably. I pulled her to me and hugged her. Ironic, I thought, she's older and much more experienced, and I barely have any sexual experience, yet I'm the one who has to hold her and calm her down. I kissed her gently and she responded.
"I'm sorry for my reaction," she whispered. "That must have been very hurtful."
"Actually, it was quite expected," I said. "That's why I'm careful not to have relationships with colleagues."
A malicious smile crossed her face. "You said you are Bi, right? Want some dick? Because I have something for you."
She jumped up, opened one of the drawers, and pulled out a strap-on dildo. She tied the straps around herself as she said, "How about I fuck you now?"
"Yay," I called. "Finally dick!!!"
*****
For me, it was a little embarrassing. I didn't tell her, but even though I was really attracted to her, and I loved her flexible, nice body, I enjoyed it more when she fucked me with her dildo than when I fucked her.
This is why I called Dr. Reese's cell phone that very same evening.
"Hello," I said, "This is Michelle Hagen."
"Hi Michelle," she answered.
"About that date..." I began.
"Michelle!" she scolded me. "What did we set up?"
"I'm just kidding," I interrupted her. "You made me the kind of guy who would lie down and run to tell."
"Oh," she said, "you really did?" And then I heard her consulting with someone. At first, I thought it was a man and my face fell, probably her husband. After a few more whispers I was sure it was a woman's voice. Is my beloved doctor a lesbian?
She made me an appointment at her hospital office and hung up.
*****
Dr. Reese greeted me with a big smile. I entered her office and, to my surprise, I saw Dr. Scott sitting in the couch cross-legged.
"So, how was it?" Dr. Reese asked, as if we were friends gossiping about our fucks.
"Divine," I replied.
"And...? Who was that? Do tell." Did she really think we were friends? Are we going to have a date today?
"Do you just want her name, or a phone number too?" I asked sarcastically.
"I just wanted to know if it was a man or a woman, and you already answered." Then she continued, "We need to talk today about your sexual function. Who came first, you or she?"
"She came before me," I replied, "twice."
"Definitely impressive," she said with a smile.
"See?" I said and glanced at Dr. Scott. "You should have date with me."
She burst out laughing. "I think I should."
Then she made me tell her everything in detail, estimating how long it had been since I came until I got hard again, and describing my orgasmic experience both when I fucked Jenny and when she fucked me. Finally, she said, "Well, it seems like your sexual function is perfectly normal. Are you still wondering if you're a man or a woman?"
Then I told her that I enjoyed it more when Jenny fucked me. The smile faded from her face and was replaced by a thoughtful look. "I think you should go back and see Dr. Scott." She said, giving Dr. Scott a questioning look, then added, "Okay, get undressed and get on the treatment bed."
"Want to help me with that?" I asked cheekily, making her mouth drop open in surprise.
"Michelle!" she scolded me, her voice stern and strict. But then came the surprise...
"I'll do it," Dr. Scott said in a cold voice that made me cringe.
I thought she was just sarcastically, but she stood up, stood in front of me, and immediately grabbed the waistband of my pants. The truth is, at one point I wanted to embarrass her back and touch her, but her precise, impersonal movements made me cringe even more. Out of the corner of my eye, I saw Dr. Reese laughing.
She checked my breasts again, my cock, which was already completely hard, and especially my vulva. "Everything looks fine," she said. "There was no anal intercourse, right?"
"That's right," I replied.
"Still, I need you to lie on your side," she said with a defiant smile. She pushed a finger up my asshole again, and that was the end of the examination.
Dr. Scott didn't wait until I was dressed and said, "Come to my office tomorrow at four."
Dr. Reese and I parted ways with a kiss on the cheek and no date.
*****
I went back to Dr. Scott and that was when the assignments started. One time it was, "I'd like you to try looking at the guys around you from time to time, think about who's more handsome, who would you like to touch you." College had already started, and I surveyed the students, most of whom I didn't know. After I told her that I thought Dylan was the most handsome, she said, "Try to imagine him sleeping with you." And so on, mission after mission.
Throughout this entire time, I continued to see Jenny. I couldn't get enough of her gorgeous body, and if it weren't for college, I would have been there every day. In practice, I had to make do with weekends only.
Then came the mission that changed my life. "I want you to try wearing feminine clothing. Try to look like a woman and go out to a coffee shop or take a walk in the mall."
*****
The next afternoon, I drove to my parents' house. My mom was in her study, talking on the phone while typing something on the computer. She sensed my presence, raised both eyebrows, and waved for me to wait. I waited for her to finish talking and said, "Mom, I need your help."
"What's wrong, honey?"
"I got an assignment from my sexologist. She wants me to go out in public dressed like a woman, looking like a woman."
"What is this? Is she a sexologist or a drama teacher?"
"Come on, Mom," I said.
She took me to the parents' room and ordered me to undress. I can't remember the last time I undressed in front of her, but this was no time for modesty games. I undressed and stood in front of her completely naked.
She pointed to my cock, that the very situation began to affect it, and said, "First of all, we need to do something about that."
"I'm sorry," I tried to joke, "it's not coming apart."
She rummaged through one of her drawers and pulled out elastic underwear. "Put this on," she said.
The thick, tight underwear crushed my cock and made me cruelly uncomfortable. "Try lifting it up," Mom suggested, and that's what I did.
She stared at my breasts and said, "I'm sorry, I don't think I have a bra to give you. All my bras would be too big for you. Do you have any regular bras?"
"No," I replied, "Just sports bras."
"Then I guess you'll have to go braless. Your chest is firm enough."
"Mom," I protested, "the idea is to dress like a woman, not like a whore."
"I didn't mean to give you a see-through dress. We'll need a dress with a moderate neckline." Then she added a biting, "And just for your sex education, you should know that even decent women sometimes go braless."
She went back to rummaging through her closet, occasionally giving me a calculating look. Finally, she pulled out a short, sleeveless dress.
"Try this one," she said, "it'll show off your beautiful legs too."
Mom looked over at me and stood me in front of the mirror. "What do you think?" she asked.
"I think it fits well," I said with a shrug. "But I think I need something with sleeves to hide my biceps."
I tried on a few more dresses, and finally, she looked at me again and said, "Wait, I think I have something that would be perfect for you." She pulled out another dress in a deep orange shade that matched my eyes, with subtle green-emerald stripes. This dress was also short, but more importantly, it had elbow-length sleeves and a neckline that exposed just a touch of my breasts. She looked at me critically and said, "I haven't worn this dress in years. If you're going to dress up as a woman every now and then, maybe you should keep it."
"Stocking without garters," she said to herself, pulling out dark, floral-patterned tights that reached mid-thigh, above the hem of my short dress. "Looks good, even sexy," she said, winking at me. "Now for shoes. Flat heels, I guess."
I didn't tell her that I had been practicing in her high heels, but I said, "Let's try high heels. Tennis players have good posture."
But it turned out that the task of finding heels was not easy. My foot was smaller than most men's, but relatively large for a woman. She rummaged through her shoe closet for a long time, looking for something that would fit me. I knew exactly what shoes I had worn when I practiced, but I didn't say anything. In the end, she found them herself. They were closed elegant shoes with high, but not very, heels in black. I stepped on them and, to Mom's surprise, I didn't fall.
Then came the makeup phase. "I suggest you undress and pack your clothes into a shopping bag. You're not going to leave this house dressed as a woman. Stay in your underwear and I'll do your makeup."
She styled my hair a little, made up my face very delicately, and then placed a black leather purse with a gold metal chain strap on the dressing table. The woman staring back at me in the mirror was definitely cute. I almost fell in love with her. I got dressed, put my purse over my shoulder and stood in front of the mirror. Yes, I would definitely fuck the woman in front of me. I changed back into my men's clothes, put on a hoodie with a hat, picked up my shopping bag, and left the house.
I drove to the garage area of the city, which was already deserted at this hour. I found a secluded corner behind a garbage container, changed into women's clothes, and drove to a pub near the airport.
It was still early and there weren't many people in the pub. I sat down at the bar and ordered a fruit cocktail. There was a cute waitress walking around the pub, with an erect chest and blond hair that was fashionably carelessly tied around her head. She was 4 or 5 inches shorter than me and had tender meat. When she came back from one of the tables, I saw a small bulge on the front of her skirt. Probably a tranny. She handed the order to the bartender and waited. I motioned for her to come closer.
"I think you have a small erection," I whispered to her. "Be careful not to be seen."
She glanced quickly at the front of her skirt and told the bartender, "Shit, I'm going to the bathroom."
When she came back, she gave me an embarrassing look. I whispered to her, "You should wear elastic underwear. That's what I do, and you can't see anything."
She stared at me for a long time, "You aren't..."
"I am," I said and pulled the front of my dress up a little. The bulge on my underwear was clearly visible.
"I can't believe it," she said. "I have a small dick that barely gets hard and now it's decided to embarrass me."
I smiled and told her again, "Elastic underwear. That's the secret."
She took the order and ran off. I made a note to visit this pub again.
Fifteen minutes later, a handsome man in his late 30s entered the pub and sat down with a sigh a few chairs away from me.
"Tough day fighting crime?" the bartender asked.
"Frustrating," the guy replied.
"At least we're winning?"
"We have no chance of winning. But at least we're getting the worst ones off the street."
The bartender approached another man at the end of the bar, and I asked the guy, "Cop?"
"Sort of."
"Bad answer," I said. "It's either yes or no, either you're the cop or you're the criminal."
He grinned and said, "I'm not the criminal." Then he looked meaningfully into my cocktail and added, "I don't even drink alcohol."
"Oh, I'll have to be more careful, Mr. Sort of Cop." I grinned.
He chuckled. "I'm not sort of, I'm with the FBI, and I don't deal with juvenile delinquents."
"I'm over 18," I said. "And even though it's a fruit cocktail, feel free to arrest me."
He gave me a thoughtful look and said, "I might have no choice."
We joked around for a few more minutes. By now I'd finished my cocktail, and he'd finished his whiskey. "The moment of truth," he said, "to arrest her or not to arrest her?"
I liked the guy and didn't want to startle him, so I didn't tell him I was hermaphrodite. Instead, I said, "I'm a tranny, just so you know," I blurted out.
"I don't believe you," he said.
"This is the moment you're supposed to tell me you've called an emergency and run away in your chopper with the siren on," I said.
"Believe it or not," he said, "I'm not scared of being with a man." I suppose a real tranny would have corrected him that she is a woman, not a man, but I saw myself as a man, so I didn't respond.
"You'll have to prove it to me," I said.
"After you prove me that you're a tranny."
"I suppose you'll do an intrusive search on me when you arrest me anyway."
"Madam," he addressed me formally, "I ask you to accompany me."
"With pleasure," I replied.
*****
It turned out that his name was Mike, and he lived on the second floor of an old building in one of the neighborhoods near the airport. If he threw me off the balcony, there was a good chance I would survive. We went up to his house and as soon as we entered, he put his arm around my waist and pulled me in for a kiss. His lips were a little salty, and his tongue was bitter, probably from the whiskey.
He stroked the exposed part of my breast with his finger and then ran his palm over my entire breast. "No bra," he whispered, "liked your confidence."
I fondly stroked his arms and felt his firm muscles. As a tennis player, I had elongated muscles, but his were rounded and hard. I slid my palms along his body, placed them on his firm butt and pressed his body against mine, feeling the hard erection arising in his pants. He must have felt my cock too, because he lifted his head from my mouth and said, "Now I believe you."
"And you still have something to prove to me," I whispered back.
He leaned over and effortlessly lifted me up in his strong arms. "Wait a minute," I protested, "I have something I have to tell you."
"You already told me," he whispered.
"Not everything," I said. He put me back on the floor. I pulled him toward the couch and pushed him over to sit on it.
"So," I began hesitantly. "The thing is, I'm not exactly tranny. I'm hermaphrodite."
"What does that mean?" A lot of people didn't know what that was.
"I have both female and male genitalia."
"Like, both a vagina and a penis?" he asked doubtfully.
"Yeah," I said, "and breasts too. And it's all natural. I was born that way."
"There's no such thing," he said.
I lifted the hem of my dress and pulled off my elastic panties. My penis responded happily and stretched freely. Luckily, Mike didn't flinch. He reached out, grabbed my cock, and stroked it. I sat down next to him on the couch, then lay back, one foot on his lap and the other on the back of the couch behind him. I grabbed my balls and pulled them toward my stomach.
Mike's gaze fell on the part behind my balls, and he whispered, "Holy shit."
He ran a finger along my slit, making my stomach jump involuntarily. Then, while playing with his finger in my pussy, he leaned over and took my whole cock into his mouth. Well, then he probably wouldn't throw me off the porch.
He didn't lick my cock, but just sucked it hard, pumping my blood into my hard piece of meat. He slid to the floor and, on his knees, continued to suck me hard and play with my wet pussy. I closed my eyes, giving in to the sensations. The pleasure on my shaft spread to my balls and stomach, while the shivers that formed in my vagina violently mixed up with my male pleasure. For someone who had never sucked a cock, he did it pretty well.
Then, he pulled his head up, pulling all my blood to the glans. At the same time, he slapped my clit, making me scream with pleasure and wonder where I would feel the release, in my cock or my clit. I put both palms on his head and screamed again, "Mike... Mikkkeee...."
Now, with only the glans in his mouth, he finally licked the frenulum, and every touch sent me into the clouds. "Oh my god, Mike, I'm cumming." Then, "Mikkkeee...."
I squirted my cum into his mouth, and he took every drop. But he still didn't let go and continued to play with my clit, until I exploded again with a scream, "Ahhhh....."
Apparently, that satisfied him and he let go and just stroked my thighs. "Take me to bed," I whispered.
He laid me on his bed and undressed. I got out of bed, took off my dress and sat down again to take off my shoes. "Leave them on," he said, "Your beautiful legs with the stockings and heels... that's so sexy..."
He finished undressing, and I grabbed his balls and pulled him towards me. I grabbed his shaft and licked the tip. Honestly, it was the first time I had touched a cock that wasn't mine. I didn't really know what to do, and my only experience was the stories I read in Literotica. I hoped that in real life it would work like in the stories.
I put his shaft in my mouth and tried to insert it into my throat, but it was too big, bigger than mine, and very thick, and I could barely get two-thirds of it into my mouth. I licked his dick inside my mouth and swirled my tongue around it. He placed his palm on my head, so apparently this part works in reality as well as in stories. I pressed my tongue to the soft part of his cock and sucked while moving my tongue back and forth. A soft moan escaped his mouth. I felt the pulses on his cock, and I realized that he was probably about to cum. Suddenly I thought about his cum, did it taste as good as it says in the stories?
I continued like this for a few more minutes until he pushed my head off him. "I don't want to cum in your mouth," he said, saving me from having to swallow, "I want to penetrate you."
I lifted myself off him happily, lay down on the bed enthusiastically and spread my thighs. Here it comes, I thought, the prick that will penetrate my virgin vagina. But he didn't rush to penetrate me. He lay down next to me and kissed me while caressing my thighs, my cock, my stomach, then my breasts. He stopped the kiss to lick my nipples and moaned, "God, you have lovely breasts."
"Mike..." I begged.
He went back to caressing my thighs and said as if to himself, "It can't be seen on you, but you're muscular."
"I'm an athlete," I replied, hoping he wouldn't ask too many questions. I didn't want him to know how to find me, I wanted to be the one to find him. He didn't ask, he just caressed me, driving me insane with anticipation and excitement.
"Mike..." I begged again.
He smiled, planted another kiss on my lips, then settled between my thighs. I opened myself up for him, and he held my balls in one hand, lifting them up, and with the other he directed his hard erection into my hole. He inserted the tip of his shaft into me and then stopped and leaned over me, leaning on his palms.
"Mike..." I begged for a third time.
He smiled again and slowly entered me. I felt my vagina slowly widen for him, deeper and deeper. The friction of his cock against the walls of my vagina sent tremors throughout my body. When he was completely inside me, I pulled him to me, enjoying the feel of his weight on my body, and kissed him passionately. He kissed me back, inserting his tongue into my mouth and playing with my tongue. Then he started fucking.
God, even after my games with the sexologist's dildo, I had never felt anything like this. My stomach trembled non-stop, and even my balls contracted forcefully. I stroked his back and went down to his hard butt, pulling them towards me. He increased the pace and slammed his hips on my butt with strong, fast movements.
"Michelle," he moaned, "you're so tight."
Then he stopped, lifted my ankles to his shoulders and as he leaned on his arms he returned to slamming me hard. It's impossible to describe the shivers that ran through my lower body. I grabbed my cock and rubbed it with the rhythm of his penetration.
I wrapped my ankles around his back and rolled left and right with light movements that increased the friction of his body on mine. Then he moaned deeply and cummed. I felt his warm fluids fill my vagina, sending pleasant waves of heat to my stomach. I grabbed him and turned him over so that his back was on the bed, and I was on top of him. Luckily, he didn't stop and continued to fuck me from the bottom up until I also came screaming, "Oh my god..., ohhh..."
I fell on his body exhausted. He hugged me tightly and buried his head in the hollow between my neck and shoulders. My cock was already hard and twisting between us. He crushed my butts and whispered, "My best fuck ever."
We lay like that for a few minutes, breathing hard, then I whispered in his ear, "Now it's my turn."
I lifted myself off him, and he pulled my butt towards him, as I dripping his cum all over his body, until I was sitting on his chest. He licked the tip of my cock and then put it all into his mouth, his tongue caressing my shaft all the way. I pulled myself back, and he lifted his legs, hugging his thighs.
"We need a lube," he said.
I winked at him and said, "I came prepared. Hand me my wallet."
He found the wallet under my dress. I pulled out a spray of lube and sprayed it on his asshole. My cock was already wet with his saliva. I stuck the tip of my prick into his asshole and squeezed. He closed his eyes and took a deep breath. It's hard to say it was easy to penetrate him, but it wasn't very hard either. The first squeeze didn't work, he took another deep breath, and I squeezed again. This time I penetrated him.
He opened his eyes and smiled. "Does it hurt?" I asked, more so I know what to expect when he'll enter my ass.
"It's okay," he said. "Go all the way in."
I entered him slowly, feeling the muscle of his anus slide along my cock until it was all inside him, then I leaned forward to kiss him. This time his dick was between our bodies. I started making coitus movements, back and forth. He let out a long exhalation and said, "Holy shit, I didn't think this would feel so good."
I laughed and said, "Maybe deep down you're gay."
"I don't have a problem with that," he said, "as long as you're the one fucking me."
The truth was, at first I had a little trouble getting out and in. The friction was just too strong, especially since every time I pulled myself out, I had to fight a vacuum that formed inside him and sucked me back in. But after a few thrusts, it got easier, and I started to slam my hips against his ass with force. I rase up and leaned on his thighs, freeing him from the need to hug them, and fucked him at an increasing pace.
He moaned with pleasure and whispered, "I never would have believed this was so much fun."
"I'm having a lot of fun too," I said. "You have an amazing ass. Hard and tight." And honestly, his ass was more pleasurable than Jenny's pussy. Too bad he doesn't have amazing breasts and soft skin like hers.
He caressed my face and asked, "Do you live far away?"
"Not that close," I replied. "I was a little afraid of being exposed near the house."
"I'd like to see you again many more times."
"I think that's what's going to happen," I grinned.
I wondered if the orgasm would also be stronger than those I had with Jenny. It was. When I cummed, my cock contracted so hard that my whole body contracted with it, and when it released my whole-body shook.
I lay on top of him, panting. Every now and then a slight shiver ran through my body, and I moved my cock inside him in gentle movements. When my whole body calmed down, I asked, "Was it really that good?"
"You have no idea. You're welcome to do it to me whenever you're horny."
"So the next round will be in my ass," I said.
Later I was on my knees, and he fucked my ass in doggy style, while I massaged my clit. When he cummed inside me, I cummed with my clit too.
*****
The next day I had a scheduled appointment with Dr. Scott and again I ran to tell... but that's for the next chapter.
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