I was in my last year of college. I was all but done with my degree in geology, except I had one class remaining. It was in life sciences, one I had taken before but failed. I was not interested in it at all. The class was a major pain in my ass. It was “The scientific study of plant life, including physiology, structure, and ecology.” Botany. I had taken it my first year and failed, so I had put it off ever since. Now I was down to the last semester and needed to pass.
There was this androgynous-looking woman in the class. She looked as uninterested as I was. Somehow, we ended up in the same study group. She and I, assuming she was a her, started talking. I asked if she needed a study partner, which she responded to with an uninterested “yes.”
After agreeing to try and help each other out, we set up a time to meet in the library. Our first interaction was mainly a bitch session. Even after that, I was not sure if this was a female or a male. Her name was Jessie, which did not help.
Myself having been in both a female relationship and also a male relationship, I was not intimidated either way. She was cute, attractive in a way, short, petite, friendly but reserved.
After the first month of studying together, I asked her out for a beer after one library study afternoon. We went to a local tavern I frequented. After a few beers, our conversation grew more personal. We started talking about where we lived, activities we enjoyed, other friends, past relationships, families, and that kind of stuff.
I had a brother and a sister. Both parents were still alive. They all lived in the same town. She was an only child. Both parents had passed away, but left her a nice inheritance, which she was using to get her degree in sports management. She stated she had played baseball in grade school and high school, but was not good enough for college ball.
Okay, so I was confused now, thinking she was a woman, but she played a man’s sport. Not wanting to pry, I just let it go.
A couple more months went by. We studied together, spent tavern time together, and even had a few dinners. I was beginning to like her. I thought that a real date was becoming appropriate. Sitting in the tavern one night, it was late, around 10:30. I asked Jessie if she would like to go to dinner, then an early show, and finish up with some dancing. She gave me this really strange look but accepted. We set up for the coming Saturday night. I would pick her up at 6:30.
Dinner was great. We just talked and talked. She seemed to be a little more open. The show was boring to me. She seemed to enjoy it. Now dancing was a lot of fun, holding her tight when slow songs were played and watching her moves on fast ones. We actually closed down the venue. It was 2 a.m. when we left.
Driving her home, my thoughts kept going to whether I should kiss her good night or try at least. That thought was vacated when we pulled up to her apartment building and she invited me in for a nightcap. Now my mind was really working overtime. Should I make a pass or not? Would she be open to play a little? I was getting hot for her. What were her thoughts?
Just inside the door, she turned, embraced me, then kissed me on the mouth and thanked me for a wonderful and fun date. I tried to pull her in for another, but she pushed me away, saying, “Time for that nightcap.”
Offering wine or brandy, I accepted the brandy as did Jessie. As we sat and sipped our brandy, she started to tell me what I thought was a story, but it turned out was actually her life.
We had previously, in one of our long conversations, talked about same-sex relationships. We discussed whether I had ever had sex with a man and whether she had a same-sex relationship. At the time, I did not pick up on the wording of her questions, only the content.
It was getting late, 1:30 a.m. I was getting tired. I told Jessie that I should get going and that we could continue this conversation tomorrow if she wanted. We agreed to meet for coffee at 10 at a little shop near her apartment. As I was getting up, Jessie said to me, “Dick, I would like to thank you for the very pleasurable evening,” as she reached out and caressed the front of my pants, right over my bulge, while looking me in the eyes.
I said, “Are you sure, Jessie?” She just stroked my bulge a couple of times and said, “Please sit down.” Once seated, she slipped to her knees, reached for my belt and zipper. Once undone, Jessie reached in and rubbed my cock, pulled it out of the leg of my boxers. One long lick up to the head, and I was rock hard. Jessie gave me a blow job that had me squirting my cum in her mouth, which she swallowed, and licked me clean.
Stuffing my now semi-rigid cock back in my boxers, she buckled my belt and zipped me up. She stood up and pulled me up, embraced me, and kissed me, with her tongue in my mouth. I think she wanted to see my reaction to kissing after she had my cum in her mouth.
On the way home, my mind was going a million miles a minute. I wanted to have sex with her and hoped that was an invitation. I guess I would find out tomorrow.
I woke up a little late. It was 9 a.m. I showered, ate an apple, and headed to meet Jessie. Being a few minutes late, she was waiting for me at an outside table. She already had two coffees and a pastry waiting. My cock had started to chub up on the drive over, just remembering the awesome blow job.
She looked different today, more masculine. Her hair was different. The Levi’s were men’s, also the tee-shirt, no bra, tennis shoes. Her tits looked smaller. I guessed because of no bra. We talked about her childhood, how her parents shielded her, but not why.
After a second coffee, she invited me back to her place, saying she wanted to show me something. On the way, she asked me again about sex with another male. I started to tell her about the first semester in college, how my roommate, both of us drunk one night, had offered to suck my cock.
As the story went, we had been out drinking, got blasted, at least I did. Sitting in the dorm room, talking about no sex for weeks, he offered to help out with that. I did not understand at first, till he dropped to his knees in front of me. Being drunk and horny, I let him suck me to orgasm in his mouth. This happened multiple times that semester. I never did him though.
Sitting in Jessie’s living room, she took my hand, asked me if I knew what intersex was.
I did not know exactly. I had heard the term before and assumed it was another LGBTQ+ thing. She went on to explain that no, it was a person born with some parts of both genders. Not everyone was the same. I was definitely confused as to why she brought this up. When she took my hand and pressed it on her crotch.
I could feel what felt like a small penis, then she pushed down farther, and I could feel warmth, like a vagina. The look on my face must have been priceless. She went on to explain she was intersex, had both a penis and vagina. After a long pause, I could see tears in her eyes. I did not know what to say. Finally, I just blurted out, "Okay, it does not matter to me."
Jessie said, “Before we go any further, Dick, I want you to see,” leading me to her bedroom. She seated me on the bed and proceeded to remove her Levi’s and panties. There in front of me was a semi-hard cock, about 2-3 inches long, and a pussy beneath it, no pubic hair.
I reached up and ran my hand over her penis and a couple of fingers over her pussy, then pulled her down on top of me, kissing her passionately. A few minutes of kissing, Jessie said, “Dick, I want to have sex with you. Will you fuck me?”
I was a guy that enjoyed oral sex, so after we were both naked, I looked at her and said, "Can I lick you?"
She whispered, "Yes."
Moving down, I did not know which should be first, so since her cock was closest, I licked up and down her shaft, took her in my mouth, all 3 inches. Then down to her pussy, licking all around her vaginal lips, finally sticking my tongue inside her. I held her penis in my other hand and lightly stroked it.
Jessie was making all kinds of noises, moans, whispering encouragement, letting me know how great it felt. After what seemed like a short time, she had an orgasm. Her pussy got wetter, and the tip of her cock had moisture on it.
Pulling me up by the head, she kissed me and whispered, "Dick that was awesome. You are the first man that has given me an oral orgasm."
We lay embracing, kissing.
I was asking, "How does fucking work?"
She said, “It is easier if you let me ride you.”
I rolled over on my back. Jessie went down on me, sucking and licking, first my cock then she worshipped my balls, finally climbing up and sinking down on my cock.
Her pussy was so tight, it felt like a vise grip. She just sat on it for a few minutes, until I could feel it loosen up some, then she fucked herself on my cock. It did not take long, and I was on the edge of orgasm, telling her I was going to cum. She just said, “Inside me, Dick.”
When I started to cum, she had a massive orgasm. Her body shook, she screamed, then went stiff like a board. Finally collapsing on my chest, breathing hard. Actually, we both were. Her pussy had a grip on my cock like I had never felt before, actually keeping me hard.
As our breathing came back towards normal, her pussy’s grip lightened up, and I slipped out, followed by a copious amount of cum.
Hugging her to me, I whispered, "Jessie, that was the best."
She whispered back, “Are you ready for another round?”
Afterwards as we cuddled and talked, she told me, "Dick you are the first man I have let see me totally naked, the first to see my penis. The other man, just one, I have had sex with, I let him fuck me from the back and kept my panties on to cover my penis. I was afraid of what he might do if he saw it."

We got up later and showered together. Seeing her naked, her boobs were small, a small handful, her penis, soft, was about an inch long, and her bottom was like a peach. She was a beautiful girl in my eyes. I was quickly falling in love with her.
After lunch, we were sitting naked. I asked her if she could just have an orgasm from her penis. The answer left some doubt. She said it always felt good to rub it. When I had her in my mouth, she liked it. I suggested we find out.
I asked her to get comfortable and went down on her. I sucked, licked and sucked more. I did not touch her pussy at all. After a good fifteen minutes, she said it felt different, then let out a loud moan, and her cock got harder; it felt like it grew an inch. Then it started to soften up.
We talked about it afterwards. She said it was different but very pleasurable. From what I could tell, no semen was ejaculated. Her pussy did drip more fluid when she orgasmed. We definitely had some experimenting to do.
A few days later, Jessie and I met for lunch. She was definitely dressed more feminine. She styled her hair more like a woman, wore some jewelry.
I was really falling for her.
All I could think about was having more sex and experimenting sexually. I was thinking about what it would feel like to have her inside me. It was something I had not ever done. The thought excited me.
After lunch, she had a couple more classes. We agreed to meet back at my place afterwards, dinner and some studying.
Study time was over. We were talking. I brought up sex with her and how much I adored her body, all of it. Her small tits, peach-shaped bottom, her tight pussy, and her small penis (I had not called it a cock yet).
Jessie, in turn, was complimenting me on my athletic body, my lovely cock (as she called it), my bottom, saying it looked cute like a woman. That gave me the courage to ask her, “Have you had anal sex?”
Jessie said, "No. Why? Do you want to?"
I said, "Well yes, but I want you to fuck me.”
The look on her face was priceless. I could tell she was definitely open to it when she said, “Really, Dick, I think I would like to try that.”
After a shower to clean out for me and for her because she was sweaty, we retired to the bedroom. I brought an extra towel to use on the bed. We started out as usual, kissing, cuddling, licking, sucking. Her cock was as hard as I had seen it. Actually, it looked bigger and thicker than previous times.
She started to suck me and lick my balls, eventually moving down to my bottom and rubbing, then licking my hole, a little finger penetration. Then some lube and more fingers, two and then three. I could tell she was getting excited to fuck me.
Jessie, please put your cock (first time I used that word with her) in me. I could tell it got her attention. I helped by pulling my legs up towards my chest, exposing my hole for her. She started penetrating me slowly, a little push, just inside, then harder, about an inch. I was looking at her the entire time. The next push, I grabbed her hips and just pulled her in all the way.
The first words from Jessie were, "Oh, it is so tight and warm."
She did not need any instructions after that. She fucked me slow and fast. The looks on her face were total bliss. After a good ten minutes, she started to slam all four inches into me. I felt her stiffen even more, then a loud moan, and she went totally stiff, her body vibrating, collapsing on my chest.
After a few minutes, Jessie whispered, “That was mind-blowing. I loved it. Can we do this again, more often?”
"Of course, sweetie, I loved it too!"
Thankfully there was no mess afterwards, no cum leaking out of me, just us cuddling. When she said, “I liked it when you called my penis a cock, it was empowering to hear.”
From that moment on, Jessie changed in bed. She became more confident, more demanding. Out of the bedroom, she was the same sweet person.
We became closer after that night. Sex between us was frequent, experimental at times. She really enjoyed the opportunity to fuck me. She enjoyed sucking me off. The taste of cum was a real turn on, an aphrodisiac, she said. One of her favorite sex things was for me to fuck her, cum inside, then she would crawl up and place her pussy right over my mouth, her cock laying across my nose, eyes and forehead, knees beside my ears, and have me lick her until she orgasmed again, pushing my cum back into my mouth.
Eventually, Jessie let me fuck her tight little ass. She squealed and moaned, saying I was too big, it hurt until it did not. Then she was like a wild woman, screaming, "Fuck my ass! Dump your load in me!" When she orgasmed, I thought I had hurt her. The wailing, screaming, moaning, body locking up rigid. Then she passed out for a moment. As I pulled out, her eyes shot open, she grabbed my ass cheek, and said, "No. Stay inside me. I love to feel your cock inside me."
One of the amazing things is that Jessie could have multiple orgasms. I could fuck her, then immediately after, her cock would get hard, just from licking, and she could fuck me.
Jessie and I did get married, moved to the south of Texas. We bought a ranch in the Big Bend area that we turned into a nudist retreat. It had a small airstrip, so people from all over the world would come and enjoy nature.
Our sexual experimentation continued. Many of our guests, after seeing Jessie, had questions about intersex. Some wanted to experience her. Eventually, we started to include intersex and LGBTQ in our advertising, which turned out to be an attraction, not on the freak show basis, but as almost a coming out experience for those individuals.
Yes, we did open our marriage to multiple partners, both male and female. Threesomes and moresomes. Jessie had her first lesbian experience, which she enjoyed. Her lesbian partners always enjoyed her small cock. I had multiple experiences with men, both as a bottom and a top. One of the most memorable was a time with a gay gentleman and Jessie. The three of us hit it off, ending up in bed, sucking and fucking. His cock was a good 7-8 inches long and thick. He was very interested in Jessie’s cock and pussy, having never experienced a pussy. We were in a daisy chain. He had Jessie’s cock, sucking and licking, when he pushed a finger into her pussy. After a few minutes of finger fucking her, she orgasmed. He was surprised at how intense an experience it was. We later fucked each other. Jessie fucked him first with her little cock.
Later, he fucked me. Jessie watched his big cock stretch my hole, watched his shaft pulsing when he deposited his cum inside me. He wanted to fuck her ass. She said no, that his cock was too big, plus I think she really wanted to get him in her pussy.
He finally agreed, with her on top and her small cock bouncing. He was okay. I gave her the first DP of her life. Him in her pussy and me in her ass.
Her orgasm was epic, screaming, moaning, curse words, shaking. Her holes got so tight I thought my cock was going to break. For the other man, his first time in a pussy, he came so hard when she froze up, he almost passed out.
He became a frequent visitor to our retreat, even bringing other gay men with him. We, Jessie and I, did not have a repeat sexual experience with him. We did hear him tell his companions the story of his first time fucking a pussy.
Jessie and I had a foursome with two lesbians. They were a married couple. Neither of them had any experience with men, cocks that is. The experience started with a conversation they were having with Jessie and her being intersex. Questions about our relationship, experiences, had she used her penis on me, those types of questions.
Jessie invited them to our house for dinner. After dinner, the conversation grew very sexual. Finally, they asked if we would consider a foursome with them. Many of the questions were focused on me. Would I be gentle, would I stop if requested, what did I expect from them.
I assured them I would respect their wishes. We could have a safe word if they wished. Jessie told them I was a gentle, loving man that would respect their wishes. I had no hang-ups regarding sex.
The three of them started out. The lesbians were fascinated with Jessie’s cock and pussy, especially how small her cock was, also no clitoris. Both the other ladies were servicing Jessie, going between her little cock and her pussy, sucking, licking, fingering. Eventually, one of the ladies asked if I wanted to join. Of course I did. My cock was rock-hard watching the action.
I started by licking one lady, then switched to the other, then switched to Jessie sucking her cock for them to see. The smell of arousal was heavy. Pussy was in the air. Jessie was sucking my cock. One of the ladies was sitting on my face when I felt a pussy sliding down my cock. I knew it was not Jessie’s. The one on my face switched around so she was now facing my feet. I could hear the lesbians kissing. The one on my cock and the one on my face, as Jessie slid her small cock into the one I could see.
This was so erotic I could not hold out. I screamed I was going to cum, expecting the lady riding me to climb off, but she did not. I held back as long as I could, finally orgasming deep inside her. My orgasm was a trigger. The other three went off to screams, howling, curse words, moans and grunts. It was an unbelievable experience.
After many years, Jessie and I sold the ranch. We moved to the Austin area, retired at the young age of 60. We now travel, mostly the USA, visiting nudist resorts, looking to introduce more people to intersex.
