Lost Interest in Sex with Girls

Editor's note: this story contains scenes of incest or incest content.

*****

I was in college and a member of a fraternity when I first met Holly. She was 19 and I was 21 the first night we were introduced. She was very cute with short brown hair and a beautiful smile. For a 19 year old she had ample size breasts. I was attracted to her immediately and she was attracted to me also.

At 21 I was still a virgin. In fact I had never in my life ejaculated. Only wet dreams. I was mildly concerned that there was something wrong with me that prevented me from intentionally cumming, but I put that thought at the back of my mind. I had never seen a naked girl in person.

My only sexual outlet since I was 18 had been to wear my mother's bra, panties, and slips for sexual excitement. I would get a hard erection wearing the lingerie but it never progressed to ejaculation.

Another concern I had was my penis size. I had no noticeable shaft to my cock when I was flaccid. Only the hood of my circumcised penis showed above the skin of my crotch and I did not have any ball sack, only a small mound between my legs that was tight against my body. I measured once when I was hard and was straining to reach 2 inches long. I had very little girth around and when aroused my cock looked like a small thumb between my legs. This was part of the reason I was still a virgin.

The night I met Holly was the first time I felt sexual feelings for a female. We spent the evening at the fraternity party and when she and her sorority sisters had to go she kissed me on the cheek and thanked me for the evening.

Holly was pledging a local sorority and was in a pledge class with eight other girls. We started dating each other about a week later and found we had a strong attraction to each other. We engaged in aggressive tongue kissing and heavy petting on our first date and it felt wonderful. She put her hand between my legs over my pants and never once mentioned the lack of size I had.

Five months into dating we had our first opportunity to spend the night together. I rented a nice motel room for us and we were laying on the bed tongue kissing and petting. Holly was wearing only her bra and panties and I had only a T-shirt and jockey briefs on. I was stroking her large breasts through her bra and could feel her huge nipples getting very hard.

For lighting in the room we had lit only two candles. All at once Holly pulled back from our kissing and got up from the bed. She unhooked her bra and pulled her panties down and stood next to the bed totally naked.

"Well" I said, "Nothing like the direct approach!"

"You should do it too" she said. "take off all your underwear."

I quickly did as she asked. Tiny penis and all. I was just about at my maximum two inches long and I was hard. I had little to no pubic hair or chest hair.

"Oh wow!" She said. "Your body is really smooth, and I love how cute your penis is. I've never had full intercourse before but I would like you to be my first. Will you fuck me? But you'll have to pull out before you cum because I have no birth control."

"I would love to fuck you, and I don't think we have anything to worry about. I can get hard, but I have a problem where I can't ejaculate." I said.

"Are you sure?" She asked.

"I have never ejaculated and I too have never had intercourse." I replied.

"OK then, let's learn how to have intercourse together." She said as she climbed onto the bed and laid on her back with her legs spread.

I was on my knees between her legs as she reached out for my hard tiny cock. She guided it with her hand to the front of her vagina lips that were really engorged and so wet they were dripping.

As she pulled my little cock into her wet lips she kept saying:

"OK Holly, this is just like putting in a tampon. Slide it inside just like a tampon."

With that I felt her warm juices engulf my little cock and when she said: "Push" I felt our pubic bones bump together. We were sexually copulated and I leaned down to kiss her. Our tongues darted in each other's mouth until she pulled off and said:

"Now slowly pull back and push forward with your cock."

I did as she asked. I was careful not to fall out of her vagina with my tiny penis.

"Now do it a little faster" she instructed.

Again I followed her instructions.

"Oh yes" she said. "That's it. We are fully fucking. I love the feeling. I'm going to pull on your cock with my two fingers to push you in deeper."

I didn't have the heart to tell her that the feeling I had in my tiny penis was not one of excitement. I felt dirty, like I was doing something wrong. Like my penis should not be used in this way. I didn't understand it but doing this did not feel right. And then something most unexpected happened.

"Holly honey. I feel like I need to pee." I said quickly.

"What? Now? Please don't!" She begged.

It was too late. I couldn't stop it. I started what I thought was peeing into her vagina, when in fact I was ejaculating a massive sticky load of semen.

"Pull out! Pull out!" She said loudly. "You're cumming and I don't want to get pregnant."

I pulled out, but I had shot a huge load of cum deep inside of her. The feeling was not at all what I expected. For a moment I felt horrible. I actually hated the fact I had a penis at all. I had the immediate feeling that I never again wanted to have sexual intercourse with a biological girl. I had just done something that for me was very wrong. I didn't know it at the time, but my first deeply held female emotions were starting to show.

In a couple of minutes as we both calmed down I managed to repress my female reactions and we cuddled together in bed.

"Well, at least we know you can cum!" said Holly. "I feel really full down there. I hope I don't get pregnant."

"I hope you don't too. And, yes, I'm glad I know I can cum."

After about 15 minutes of calming down Holly turned to me and said:

"I want to do it again. I don't care about what happens. I want to fuck you again. Do you think you can get hard?"

"It's already starting to happen" I replied. Being young is a great advantage.

"Oh great! I can't wait to feel you inside me." She said.

As we prepared to have a second session of intercourse Holly turned to me and said;

"I haven't told you everything about my sexual experiences."

"Oh..." I said slowly.

"I've never had full intercourse before, never. You were my first. But I have done everything else but that before."

"Really?" I said.

"Yeah. I have a sister who is eight years older than I am and she is married and has two kids. When I turned 18 she hired me as her afternoon babysitter because she works in a bank and doesn't get home until 6:30pm."

"So this was over a year ago?" I asked.

"Uh Huh. It started as a summer job and when school started I had afternoons off so I just kept babysitting so she didn't have to pay a stranger full time to take care of my niece and nephew."

"What did you do?"

"When I turned 18, my brother-in-law, Bob gave me a present that he told me to open only when I was alone and not show it to anyone. I did as he asked and it was a box of porn magazines and graphic novels. I was shocked, but also excited at the idea he thought of me that way."

"You didn't tell anyone?" I asked.

"No. I didn't want to hurt my sister and I was a little shy about it. The next time he and my sister were over at the house he made it a point to get me alone and ask me what I thought of his present. I told him I was a little surprised. He told me he wanted me to see what he and I could do together if I wanted to."

"Wow" was all I could say.

She continued with her story saying;

"I had only been babysitting for about two weeks when Bob came home early from his job knowing that I would be there and the kids would be down for their nap. I asked him what he was doing home so early and he said he was there to see me. I had a tentative feeling that gave way to excitement as he sat on the sofa next to me and put his hand on my leg. I was just wearing a two piece bathing suit and he leaned in to kiss me."

"What did you do?" I asked.

"I turned my head away and he said 'it's just a kiss baby and I think you want it.'" She continued.

"He was right. I did want to think that he wanted me. So I turned back to him and we tongue kissed very deeply. His tongue was way into my mouth when I felt the crotch of my bathing suit getting wet."

"Did he notice?" I asked.

"He did when he slid his hand down my front and inside my bathing suit. His fingers slid between my pussy lips. I pulled his hand away and said 'NO' in a stern voice. He pulled back and kissed me on the lips again. I told him I was not comfortable doing this anymore and we stopped."

"Did he stop and respect your wishes?" I asked.

"He did that day, but in the weeks and months ahead he came home from work early at least three times a week. Every time we were alone things went a little farther. We both ended up nude together and I kissed and licked and sucked on his huge round cock. I swallowed his cum several times and he licked my pussy until I thought I was going to scream it felt so good."

"But he never had intercourse with you?" I said with amazement.

"No. We never did. He would put his erect penis head right on the wet lips of my vagina and plead with me to let him slide it in, but I always said 'NO' and he respected that limit, but didn't really like it."

"That's quite a story" I said. "Do you still babysit for them?"

"I do, but now he can't take my virginity because I gave it to you. It's something he will never have."

"Thanks...I think" I said.

"I don't want to hurt your feelings or anything" said Holly, "but Bob's penis is five times as big as yours is and much, much, bigger around. But you felt great inside me and I want to do it again right now."

I didn't want to tell Holly that it felt strange for me to be having sexual intercourse as a male. I did have a penis between my legs and it was getting hard even if it was only two inches long when fully erect. But in the back of my mind something was telling me I shouldn't be doing this. I felt very dirty. Holly's story about her brother-in-law's big cock got me kinda excited.

My cock was fully hard as Holly put it into her mouth and licked the tiny bulb of a head it had. In a flash she pushed me over on the bed on my back and she straddled me lowering her vagina right onto my penis. She pushed down and I was inside of her as deep as I could go. Our pubic bones banged together as she moved her crotch up and down on me. She did this for at least five minutes. A couple of times my tiny dick fell out of her but she quickly inserted it back into her.

"Are you going to cum?" She asked.

"I don't know. I haven't got that feeling like before." I said.

"Let me do this" she said as she leaned forward and began to lick and suck on my nipples. I gasped for breath as the most wonderful feeling came over me.

"Oh my God! That feels great!" I shouted.

"And your nipples are getting bigger than mine!" She said with amazement.

"I can't hold it. I'm cumming...I'm cumming harder than before!"

With that I felt a squirt of cum bigger than before shoot out of my tiny dick. And it didn't stop squirting. It was as if I were peeing it was coming out so much and so long.

"Oh my God, Oh my God" was all I could say as I gasped for breath.

At the same time I felt Holly's cunt lips squeeze my little cock tighter and tighter as she let out a little scream and then she too gasped for breath as her vagina clamped my penis even harder.

"I think I just had a huge orgasm." She said. "I've never experienced anything like that. I really love fucking you!"

"I like it too" I replied, hoping she unable to tell that I was not telling the truth. I enjoyed the feeling, but I felt it was wrong for me to be doing this. In the back of my mind I really wanted to be the girl when having sexual intercourse.

Over the next four months Holly and I dated every weekend and saw each other at school during the week. We had intercourse several times. She told me she was taking birth control pills she had gotten at the campus health center.

I was more sexually active than I had ever been in my life but feeling like I should not be having sex as a male. My estrogen levels must have been high as I really wanted to experience sex as a girl. And to take things further I wanted to start daily living as a girl. I began to buy my own lingerie. Panties, training bras, slips, and soon dresses, and nightgowns. Even while Holly and I dated I slept every night wearing full cut nylon and lace panties under my long nylon and lace nightgown. I did not tell Holly what I was doing and I always made sure I was wearing male underwear when we were out together. But wearing male jockey shorts only convinced me more it was wrong for me to do this. I belonged in a training bra and panties. They were much more comfortable for me.

One night after Holly and I had finished having intercourse, she turned to me as we were lying in bed and asked if there was any kind of kinky type sex play I would like to do with her.

"What do you mean?" I asked.

"Oh, you know anything to spice things up. Maybe tying me up or putting a blindfold on me. Would something like that turn you on?" She asked.

"Well...I really enjoyed wearing my mother's panties and slips and bras when I was younger and I was kinda hoping you would find it exciting if I wore lingerie while we fucked." I said this in a sheepish voice hoping she would understand.

"Really? Is that something you would like?" She responded.

"I'm pretty sure I would." I said.

"Wow...it sounds kinda kinky and I maybe could get into it, but where are you going to get the lingerie that fits?" She asked.

I decided to tell all and take a chance on her dumping me. "I have a full collection of panties, training bras, slips, garter belts, and stockings. I even have a few dresses that look good on me. I also have a full wardrobe of nightgowns and baby dolls for sleeping."

She paused for a moment and looked at me. "You're not kidding, are you?" She asked.

"I'm not. I really like having a fantasy of being the girl during sex." I told her.

"Don't worry. I think it would be kinda fun to see you dressed up. It might add to my excitement. Can you have an erection when you are fully dressed?" She asked.

"Not a really hard one." I replied.

"Why not?" She asked.

"I'm not sure. It's as if the female in me takes over and prevents any kind of male sexual stimulation from taking place. My nipples get really big and round and very hard. You noticed this yourself." I was telling her everything.

"I did notice your nipples are super sensitive. I have also noticed how tiny your cock is when it is erect. Do you not like having an erection?" She asked in a caring voice.

"Not really. It doesn't feel right for me. It makes me feel dirty and unfeminine." I said.

"Wow! I had no idea you were so into being a girl. I mean, it's fine with me, I just had no idea it meant so much to you." She said.

"Well, it's not something that is easy to talk about, but I feel so close to you it is something I feel we can share." I confided.

"Of course baby" she responded. In my human sexuality class I have read something that you may find will help you. I'll bring it to our date tomorrow night. Why don't you wear your full set of lingerie under your male clothing and bring along your nightgown and I'll help you get what you want."

The next night was a Sunday and we got together in the late afternoon. We were in her apartment and she told me to take off my male clothes. I did as she asked revealing my lingerie which was a training bra of nylon and lace, a pair of full cut nylon and lace panties, a nylon and lace half-slip and camisole. All white. My nightgown was a long sleeve full length nylon and lace pink gown and I had it in a bag on the side.

"Wow. You look really pretty!" Said Holly as she looked me up and down in my lingerie.

"I got something for you that I think you are going to want to wear all the time and I can help you do it." She said.

"What is it?" I asked.

"It's what called a male chastity device. It's a metal cage with a lock on it that will prevent you from having an erection." She slid the device out of a black pouch as she described it.

"I had to find one that was small enough to fit you, but I think I got the size right. This ring will slide around behind your little ball sack and this little cage on the front will slide over the head of your cock. Pull off your panties and let me insert you into the device." She said.

I did as she instructed and after a couple of tries at pulling and pushing my tiny male genitals into the metal device I heard a "click" sound as she closed a tiny padlock into place.

"Is that a padlock?" I asked.

"It is...and I'm the only one with a key."

"How will I pee?" I asked.

"There is a slot in the front of your cage that will allow you to easily pee when you want." She said in a matter of fact way.

"How long do I wear it?" I asked.

"I read if you wear it continuously for at least 90 days you will find it very difficult to ever have and erection. At six months of continuous wearing you will permanently destroy your ability to become erect. And at nine months or more there is a very strong likelihood you will become impotent. You will, in short, become what you want to be; a girl."

I found what she was saying exciting.

"Will I wear it under my clothes?" I asked.

"Absolutely. And they recommend you wear only panties as it will fit much better. For you it looks to be a perfect solution." She assured me.

I pulled my panties back on and felt the metal device fit easily between my legs.

Holly continued telling me what to expect; "What this will do is restrict the blood flow into your tiny penis. When the spongey chambers that fill with blood to make you hard are denied any fluid, the skin in them will begin to grow together and in the future it will be impossible to ever again have an erection. The book says most males who stay locked for a full year usually opt to have surgery to remove their testicles. When you do that your testosterone levels will disappear and your estrogen levels will take over. Then you'll grow some hips and breasts and fill yourself out as a woman."

I was really getting excited at what she was saying and felt myself becoming erect, but the metal cage began to hurt so bad I quickly stopped the urge so the pain would subside. I began to accept my new role as that of a female. I was excited with the possibilities.

But Holly wasn't finished with her news on our sexual relationship. She said; "Since we are telling each other everything, I should let you know I have been having full out sexual intercourse with my brother-in-law Bob every weekday. I started a few days after you and I lost our virginity to each other."

"Oh wow!" I said. "I'm sure he's a lot bigger than me."

"Oh he is. About five times as big. And I've been letting him ejaculate inside me without any protection for over a month now. He's been coming home early every day so he can fuck me and we've been really going to town and have wild passionate sex. It's been a real workout."

I really didn't know how to respond, but I was secretly happy for her.

"My sister has no idea and Bob shoots such big loads inside me my panties are always wet. I have to wear a skirt to prevent the wet spot from showing. I don't want to hurt your feelings but he makes love like a real man and it turns me on." She said in a loving way.

"Don't worry about me" I said quickly. "I know I'm really a girl at heart. I've been feeling it is wrong for me to be putting my tiny cock into your vagina. I have a very real desire to be the one putting a big, rock hard penis from a real man into my mouth."