His Vagina

These stories are fantasies that I have come up with and hope to someday experience them in real life but right now they are staying in the closet (pardon the pun). They get me pretty excited and sometimes its an arduous task between relieving the sexual tension they create and actually finishing them. Please excuse any grammatical or spelling mistakes. I hope you are entertained by my work as much as I am. Please feel free to leave a constructive comment or reach out through a message - I love to talk and explore what others feel, experienced, and want. All characters are over 18.

- GBiC

After divorcing my wife we sold our house and both bought houses in town that we could both afford based on the proceeds from the house sale and our salaries. All three kids graduated high school and were off to higher learning institutions. The oldest, my daughter, was getting her masters.

The Ex and I went to parents weekends together but always got separate accommodations. She always wanted to split one because I think she really wanted to be together again but that ship had sailed for me. I still like women but my interest in sexual partners liens towards men now and during these visits I always hook up with a hot young college stud who is looking for a daddy to take care of them, if it's just for a night.

Out of the blue I decided to visit my daughter at school. I texted her prior to leaving and said I was coming down for a visit. She was excited to see me. After checking into my hotel, I picked her up and took her to dinner. Afterwards she asked if I wanted to go to a party with her and I asked if I was too old for her crowd.

She assured me, there would be a lot of faculty there as well. She was a TA, so I figured what the hell, who knows, maybe I will find someone to sleep with tonight.

As we were walking into the building where the party was being held I noticed a sign saying it was an LGTBQ+ mixer and I pulled my daughter to one side and pointed to the sign and asked her if there was something she wasn't telling me. She was surprised that I didn't know she was gay. Apparently, she came out to her mother last summer but realized she never told me. She then said, now you know.

I just told her I was proud of her. She told me thanks and pointed me to the bar and told me she was going to look for her friends and left me to my own devices.

At the bar I got a beer and then started scoping out the various guys in the room looking for someone who strikes my fancy.

Just then a guy approaches me, doesn't look like a professor but also not a young college kid either. He didn't look like your typical college kid, he was older but my Gaydar was going off and my penis got hard indicating a missile lock.

I smiled and he smiled back and said, "I have never seen you here before. My name is Charles." He offers his hand.

We shook hands but I didn't let go right away. His hand was soft, almost dainty in a way. "Matthew. I am not from around here, just visiting my daughter, who brought me to this party and then disappeared."

"Oh, who's your daughter?" He asked.

"Tara Jones, or she might go by TJ." I said.

"Ah, yes, TJ. She is one of our best TAs in the Economics Department." He said.

"Please don't be offended but you look too young to be a professor." I said.

"None taken, I get that a lot but I am actually 35 and have been at this for 5 years now." He said.

I looked him up and down and wondered what he would look like with no clothes on.

"I bet you are wondering what I look like with no clothes on." He said matter of factly.

I blushed. I was about to copp to it when someone pushed me from behind into Charles. Both my hands went to his waist to stop me from completely crashing into him and we were suddenly face to face.

We looked into each other's eyes with a longing and then he put his hands on the back of my head and pulled me into a kiss. Our tongues met and fought for dominance and the world around us ceased to exist. I pulled his waist into mine and ground my crotch into his and we moaned at the sametime.

Then I heard someone clearing their throat next to me and I turned to see my daughter standing next to us with her arm around the waist of an older woman who was drop dead gorgeous.

"Father!" She quietly exclaimed in an admonishing tone. "Is there something you would like to tell me?"

"I am bi-sexual! I guess that means I am out of the closet." I said grinning.

Then she was all smiles and said, "I knew it!

I was wondering why you and Mom split up so quickly after Jimmy left the house for college."

I turned my body towards her but kept my arm around Charles' waist and said, "Actually honey, she said she didn't love me anymore and there was no point staying together. When we stopped being intimate, I realized that I fancied men and women equally.." I said proudly.

"Dad, this my girlfriend Sheila, Sheila, this my father Matthew." She formally introduced us.

I reached out to shake hands and when she grasped mine I pulled her into my arms and kissed one cheek and then the other.

"It's a pleasure to meet you Sheila. Take good care of my daughter. Now, if you two will excuse us, I think Charles and I are going to go back to my hotel and continue what we started. Is that OK darling?" I said almost mockingly.

I turned to leave, holding Charles hand, pulling him with me.

I heard my daughter say have fun.

I led Charles to my car and said, "Do you want to follow me?"

"I walked."

I led him to the passenger side, opened the door for him and he slid into the passenger seat but before I closed the door he pulled me down for a kiss.

Then I left his delicious mouth to get in on the other side. I looked at him and he looked so sexy that I had to have another kiss but he stopped me and said, "This is my first time." there was a pause and then, "With a guy."

"We can take it slow and I won't force you to do anything you are not comfortable with." Then I leaned in and kissed him. He kissed me back.

We didn't talk much on the drive over to my hotel but his hand was in my lap the whole time slowly stroking my penis through my pants.

Arriving at the hotel we hurried in and when the elevator arrived I pulled him in with me, pushed the number to my floor and then pressed against him and we started kissing.

The elevator arrived at my floor with a ding and I was pulling him down the hallway towards my room. I opened the door with the key card and then we were in the room. He pushed me backwards towards the bed and then I fell backwards onto it.

Charles climbed on top of me and we kissed again. I was holding and squeezing his ass cheeks and he was moaning between kisses.

He pulled up my shirt and attacked my nipples while rubbing his shin back and forth over my rock hard penis.

Then his hands were fumbling with my belt and I helped him open it up and he got off the bed but stayed between my legs and pulled my pants and underwear down freeing my penis and taking it into his hot mouth. Keeping me in his mouth he got my pants and underwear off me completely and then sucked my penis as deeply into his mouth as it could go.

Charles' mouth on my penis was mind blowing, the intensity of his suction combined with the pressure that my plug was having on my prostate brought on a tsunami of pleasure. I eked out that I was about to cum and he stayed rooted to my penis making all sorts of happy, yummy noises.

I could feel my balls start to tighten and my penis expand. I arched my back as a shiver of pleasure shot through me and then I was flooding Charles' mouth with semen. He didn't miss a drop.

When I got too sensitive I started squirming and he got the message and left my penis to plant a cum laden kiss on my lips. His tongue tasted wonderful as it pushed my sperm into my mouth and I savored the sweet and salty taste.

I slid a hand under his pants and was reaching for his penis but didn't find one. Opening my eyes in surprise as my hand slid through a wet mess of pubic hair to cup a mound with something poking out of it.

Charles left my mouth to arch his back and moan loudly and I realized that Charles was trans! This night was getting better and better.

I slid my middle finger between his moist lips and then pushed it deep into his hot, wet hole. He groaned and he ground his mound into my hand.

"Oh god, give me another finger!" He moaned.

I pushed another finger into his already tight channel and his vagina gripped my fingers hungrily. When I started swiping my thumb back and forth over the head of his penis he lost it all together and I felt a gush of wetness shoot onto my wrist. Charles let out a wail and his whole body shook through his orgasm.

It was so hot watching him cum on top of me.

He collapsed next to me and I withdrew my hand to lick off his cream. The taste reminded me of Joan and Nancy's vaginas the last time we hooked up.

I turned to him and watched him laying next to me still panting. I looked at his face closer now and there was nothing in his facial features that you could see were feminine. I am usually pretty good at that but looking at him closely the only thing that could give him away was his lips but the beard hid them pretty well. I think I have a thing for bearded men.

I leaned in and gave him a kiss and then Charles opened his eyes, pushed back a little and smiled at me. I gave him a big shit eating grin.

"When you said you were Bi, I figured you would have no qualms with my equipment. I have only been with women but being around you tonight and kissing you has me more than ever curious of what it is like to have sex with a man." He said.

"This is a first for me and I love it. It's the best of both worlds." I said and I kissed him.

"I would love to taste you. Why don't you take off all your clothes and sit on my face?" I suggested.

"Do you still call it a vagina? Or is there something else I should call it?" I asked.

"No, I just call it My Vagina and you can call it that too. However, I don't appreciate it being called anything other than that, it's not a pussy or any other derogatory term." He said adamantly.

"I would really love to eat you out and suck your penis. Is that OK? I know some trans people sometimes have genital dysphoria and I don't want to do anything you are uncomfortable with."

Charles got off me and took off all his clothes and I got a good look at his slim body. He had no breasts to speak of but big nipples. His mound was really hairy, which I love, and protruding out of it was his penis that looked to be about 3 inches long and very suckable.

Before climbing back on top of me, he replied, "No, it's cool. I like getting eaten out. I don't get a lot of head because quite a few of the lesbians that I have dated aren't into penis'."

With that he climbed back on top of me seductively. He stopped at my crotch and gave my balls a lick and then kissed my shaft. Dragged his tongue up my happy trail and then stopped at my breast and before kissing my nipple used both hands to squeeze and hold my breasts.

I moaned at his touch and he looked at them and then looked at me.

"I have Klinefelter Syndrome. I was born with an extra X chromosome and have had breasts since puberty. At times it's embarrassing, like in pictures, but I have gotten used to them." I said somewhat embarrassed.

"Well, I think they are wonderful." He then started licking my nipple and I moaned. I put my hands on his head and we started sucking one nipple and pinching the other. Women have described to me in the past what it feels like for them but when this happens to me I get chills all over and my penis acts like a lightning rod. My plug was stimulating my prostate and I was getting anxious.

He moved his mouth to my other nipple and I was squirming at his touch. I love the feeling but if it comes on too fast or too hard they get really sensitive. Then he moved off and kissed me on the mouth. I could feel his vagina dripping onto my hard penis. I thrusted into him but didn't penetrate and he moaned.

Finally he moved off and was squatting over my face. I could smell his excitement and his hairy bush was matted down with his dew. His penis was rock hard and looked so suckable.

Before I pushed my tongue inside him I held his thighs and buried my nose into his pubic hair. I have this thing for pubic hair in which I like to breathe in my lovers' scent. It really turns me on. I kept at it until Charles started shifting back and forth looking for some friction. His Vagina looked hungry for attention. His labia were really engorged, coated in his cream, and sticking out. Equally, his penis was throbbing and definitely needed to be sucked.

Pursing my lips I pushed them between his wet labia and pushed my tongue into his hole. He tasted wonderful as I licked and penetrated him with my tongue, drawing out his cream. I moved my hands to his butt cheeks and gave them a squeeze. I could feel him shifting and it looked like he was arching his back in pleasure.

I moved a hand to his left nipple, pinching and turning it between my fingers. This elicited a cry of ecstasy and he grabbed the back of my head and ground his vagina into my mouth. I could sense his desperation for a little more stimulation that would push him over the edge but I wanted to prolong it.

Turning my head, I ran my tongue from the joint of his leg towards his knee and then back again. He groaned in frustration.

I kissed his labia and took a small lick through his folds and then plunged down on his penis and slid two fingers into him.

With a wail and a convulse he came on my face. His cream squirting out violently and I got my mouth open in time to get my mouth full of it. It was salty and bitter and smelled more like ammonia.

He shuddered through his orgasm and didn't let go of my head while he humped my face as I kept sucking his penis and pumping my fingers in and out of his vagina. He relaxed only for a second before another round of shuddering and moaning overtook him in what only could be a second orgasm.

When he couldn't take any more he fell to one side panting. His eyes were closed and he was smiling. Then he reached out and started stroking my hard penis.

Without letting go of me he turned to me and opened his eyes looking into mine and smiled.

"Do you want me to put on a condom? I have some in my bag over there but you don't have to worry about getting pregnant because I am fixed." I said.

"Thanks for letting me know but I had a hysterectomy with my top surgery so there's no chance for me to get pregnant." He said gleefully.

"I have fantasized about this moment for years but never found the right guy who I wanted to take my virginity. I can't wait to feel you cum inside me." He said seductively as he lined up my penis with his vagina. I could feel my head parked between his outer labia.

"Charles, after I cum inside you will you let me eat my cum out of you?"

He smiled and said, "Oh my god, that would be so hot."

I could just make out the small scars from his top surgery. "I love that your nipples are so big and I can't wait to suck on them." I said seductively.

He blushed and then slowly sat back and my penis started to push in. He controlled the action, sinking and then pulling back, sinking deeper, pulling back and finally I was balls deep inside him.

His face had this feigned look of shock, his mouth was open and his eyes closed. There were little flexes of his muscles reflected in winces in his face and then finally his face took on a serene and satisfied look. He was wet and tight and he needed a couple of tries until I was balls deep in his vagina. It was incredibly hot and tight, and I could feel his walls pulsing around my penis. I gave him a small thrust and he grunted then leaned down and presented a nipple for me to suck on.

Charles made these grunting sounds as he moved up and down on my penis and I sucked on one nipple and played with the other.

He was holding my shoulders and I put my hand on his penis and started stimulating it causing him to hump me even harder. I switched nipples and I felt his vagina gripping me harder. I wasn't even close to cumming but he exploded on top of me.

He pulled my head off his nipple and mashed our lips together and continued humping me while shuddering and moaning into my mouth.

Something about a sexual act and kissing really turns me on and I felt my pleasure start to rise Charles continued thrusting and then arched his back. His Vagina felt like it was going to rip my penis off of me. I felt my orgasm rush through me like a freight train then I was filling his vagina with my semen. He came again and it was so sexy to be coming at the same time with him.

We stopped kissing and sat there panting with our foreheads together enjoying the afterglow. I could feel my penis start to slip out and that's when I told him to get up on his knees over my face so I could watch my cum drip out of him.

I fell back on the bed and my penis slipped out of him but he put his hand between his legs so my cum wouldn't slip out and he duck walked on his knees and stopped when he was over my face. His Vagina and penis were beautiful. His pubic hair was nicely trimmed around the top and sides and he was bare from his labia to his rear hole.

Removing his hand from his mound I saw his penis move up and down and his slit push out followed by a large amount of semen oozed from his vagina and gravity took over causing it to elongate and drip into my open mouth and onto my chin. The string broke and the last bit dribbled onto his leg. I swallowed what dripped into my mouth and watched the little river of semen slowly move down the inside of his thigh. When it stopped, I ran my tongue along the inside of his thigh and licked up the sperm trail. His moaning was music to my ears and penis as it started to get hard again.

Putting my hands on his hips I pulled his vagina to my mouth and started eating him again. The mixture of our fluids tasted wonderful as I pushed my tongue into him and drew it out over and over again.

His penis was pulsing and when I was finished cleaning him out I took it in my mouth.

He squealed because it must have been too sensitive but I gripped his butt hard and kept my mouth attached to it, all the while sucking hard on it and I was able to coax another orgasm out of him, this one included a spray of his juices all over me. Charles fell off me onto the bed and I reached over to cup his mound but he grabbed my hand and said no more for now.

Kissing his shoulder I asked him if he wanted to get into the shower and he agreed.

Once the water was hot enough we both got in and took turns lathering each other up. After rinsing off all the soap I pushed him gently to the wall and pushed a soapy finger into his other hole. He moaned and told me he's never had anything in that hole before but would like to try it.

I knelt down and opened his butt cheeks and stuck my tongue into his hole and he squealed in delight. Then I got up and told him to spread his cheeks apart. I took the bottle of conditioner and squeezed some out into my hand. Dipping two fingers into it, I pushed one digit into his hole and let him get used to it and I slathered the remaining conditioner all over my penis.

I started pushing a second finger into him and I heard a sharp intake of breath so I stopped and kissed him on the shoulder. "You are doing lovely sweetheart. Let me know when I can push my second finger into you."

He looked back at me with wide eyes and asked, "That's your fingers?"

I smiled and leaned in for a kiss and I felt his body relax and without waiting for him to tell me to proceed I pushed my second finger all the way in to him and twisted my wrist.

"Fuck!" He shouted.

"Give me your penis now!" He demanded.