A Cross-dressed Cuckold

My name is Cindy, I live full time as a woman despite the fact I have a tiny stub penis and an even smaller shriveled ball sack between my legs. I am married to a female named Bonnie. We have been married for over ten years. I love and adore my wife and she is the same with me. I was a mostly naïve male who it was well known, was an heir to a rather large sum of money. How Bonnie and I got to this point in our lives is an interesting story.

Before we were married my wife to be, Bonnie, insisted we not have sexual intercourse until our wedding night. We engaged in all other forms of sex play; tongue kissing, stroking her breasts and nipples over her bra, sliding my hand between her legs over her panties. She stroked my erect penis but only over my jockey shorts. She never touched my naked erection and I was never allowed to touch her naked pussy. I could stroke between her legs and push in between her wet lips but only with her panties on and in the way.

I really loved spending time with Bonnie and she felt the same about me, she just would not allow sex between us. She was always into dirty talking when we were heavy petting and I loved how it made me feel when she started up.

Because my penis was clearly on the small size when it was erect, Bonnie always let her dirty talk center around my tiny cock.

"My little boy sure feels little in his underpants." She would say. Or "that is your penis and not your clitoris, isn't it?"

I always took this as playful dirty talk and since I was not allowed to show her my naked erection and I could not see her naked pussy I never responded in a negative way to her language.

When we both agreed to marry we were in our mid-20's, Bonnie told me she still wanted to wait until our wedding night to have sexual intercourse. She also said to me she felt sorry for this and asked if there was any type of release I enjoyed privately. She told me she had no problem with me relieving my sexual tension in this way. Since our wedding was just a little over a month away I decided to tell her about my sex play that I had enjoyed for many years.

I felt secure enough to tell Bonnie that I had enjoyed stripping fully naked and sneaking into my mother's lingerie dresser when she was not at home and putting on her panties and slips. The look and the feel of the lingerie on my body was very sexy for me.

"Oh wow! I had no idea you were into something like that!" Said Bonnie smiling.

"It's not something I have shared with anyone." I replied.

"Do you still like to do that?" She asked.

"I do, and the way it causes my nipples to become erect and large is really exciting."

"When your mother was alive did she know you were doing this?" Asked Bonnie.

"I'm fairly sure she had no idea. I know she wore very feminine full cut panties with lots of nylon and lace. Her slips were just beautiful with wide lace around the hems." I replied.

"Is this something you would like to do with me?" Asked Bonnie.

"Well....Only if you would find it sexy." Was my reply.

"I've always thought it would be fun to have sex play with another girl. If the other girl had a cock and balls that would really be sexier than I imagined. When we get to our wedding night let's play together and have a good time. In the meantime, if you want to wear some panties and some slips, I would have no problem with that." Said Bonnie smiling.

I had not really worn my mother's lingerie for at least three years, but getting the green light from Bonnie was a welcome opportunity. My mother had passed away four years ago and when I packed up her things I kept a box of her extensive lingerie collection of bras, panties, slips, nightgowns, and garter belts and stockings. I now felt more open with Bonnie as I sorted through my mother's panties and slips deciding which ones I would like to wear.

Our wedding night finally arrived. Bonnie looked beautiful in her white satin and lace wedding gown. I wore a handsome tux. In our wedding night hotel we stood looking at one another and watched each other slowly undress until each of us were totally nude. We kept the light in the room on and for the first time I saw Bonnie's fully shaved pussy lips that were slightly swollen and looked very wet. Bonnie saw me naked for the first time with my pubic bush and said;

"Well, before we begin, we're going to need to shave you between your legs; besides, it will make your little penis look bigger if it is hairless."

Bonnie took control and led me to the bathroom and in no time my pubic area was shaved totally smooth.

"There we go. Much better, now the fun can begin. Tonight, you are going to be the girl and I am going to be your wife. I want you to put on this wedding night baby doll nighty and panties and I will wear the pajamas you packed for yourself." Directed Bonnie.

It was very exciting to hear Bonnie tell me what to do when it came to having sex. My little penis got hard immediately and stood straight out about two inches. Bonnie watched as I pulled on the oversized panties with lots of lace around the leg openings. I then put on the very feminine top that had chiffon and lace on it with puffy sleeves. Bonnie was still fully nude as she watched me.

"Oh you look very pretty! This is going to be fun! Now follow me into the bathroom, I want to put a light amount of lip gloss on you to give you a more girly look."

I was startled at what I saw in the mirror. Just a little red lip gloss really made a big difference. With my baby doll on and my hair pulled back I had a very feminine look. My little penis pushed the front of my panties out as Bonnie leaned into me and we shared a deep tongue kiss.

"Let's call you Cindy." Said Bonnie as she pulled on my male pajamas.

"Now Cindy, get into bed with me and let's see if you can fuck me on our wedding night." Said Bonnie in a low voice.

We again started kissing as my hands went into the fly on Bonnie's pajamas and for the first time my finger slid into her wet pussy as I felt her clit begin to grow in size and length. I kept stroking her clit and felt a tiny helmet on the tip of it as she moaned when I pulled on it.

"Take off your panties, and pull down my pajama bottoms and let's fuck! Fuck your new wife and let me suck on your nipple through your nighty!" Demanded Bonnie.

I did as she asked and I was on top of her with my penis just a little bit longer than it was before. Bonnie spread her legs as I pushed forward toward her pussy and the helmet of my little cock slid quickly between her wet lips. As soon as the helmet of my cock entered her I immediately ejaculated. We had been copulated less than a few seconds when I blew my load.

"Oh honey, I'm sorry. I've waited so long for this moment, I had no idea this is what would happen." I apologized.

"Don't worry about it baby. I felt you cum and that was a good thing. We have a couple of weeks to get better at this, besides, it was super sexy to have you on top of me in that sexy baby doll." Assured Bonnie.

Over the next couple of weeks we did get better at fucking. I was able to hold out ejaculating for a minute or two and I was able to get my small cock shaft fully inside Bonnie's cunt. Over the next several months this is how our sex life went. We never had sex unless I was dressed as a girl and we began buying me a rather extensive collection of beautiful, vintage, lingerie. Lots of lace and nylon. Panties, half and full-slips, training bras, nightgowns, stockings and garter belts. Bonnie had me shave all the hair off my body and daily put on body lotion to make my skin extra soft.

After about six months or so we bought me some dresses that fit me very nicely. They were of the sun dress variety with wide skirts which called for petticoats underneath and we purchased those too. It was a fun game we played when Bonnie would put her hand up under my skirt and tug on my little cock through my panties. It was a game to her to have me cum in my panties which I usually did quite quickly. I wore my feminine clothing a few times a month when we would enjoy sex play.

After about a year of marriage Bonnie came to me with a rather serious suggestion that I found myself more than eager to accept.

"Cindy honey, I've been thinking, what would you say to you wearing your girl clothes full-time and on a permanent basis?" Asked Bonnie.

"You mean assume the look of a female on a full-time basis? I would never again wear any male clothing? I asked.

"Yes, that's what I mean. We'd let your hair grow out longer and get it styled and I'm going to teach you how to apply your make-up and I want you putting it on every day. At night you are only to sleep in nightgowns with your panties on underneath." Said Bonnie directly.

"I think I'd really like that. I can become Cindy on a more than genuine basis." I answered with a smile.

"Well, there a few other things too." She said.

"Like what?"

"I would like you to take a couple of pills every day, one that will stop your body from producing sperm, and the other will make your tiny penis completely limp on a full-time basis." Said Bonnie.

"You mean, make me impotent as a male?" I replied.

"Yes. As my live-in girl I want there to be no physical possibility that you could ever get me pregnant...Not that there is now with your little cock and pre-mature ejaculation, but with the pills we can chemically neuter you to the point you will feel much more comfortable in your role as Cindy."

"So when we do this it will put an end to us having any type of sexual intercourse." I sighed.

"Yes it will, and it is for the best for both of us. You have trouble getting your little cock big enough to fuck me, and when you do, you cum so fast it makes it difficult to have a meaningful sexual experience for me. Besides, you are going to be so much happier being a full-time girl." Said Bonnie.

"As much as this is a little shocking, I know deep in my heart you are right. I absolutely love being a girl and I do not like my sexual performance as a male at all. I want to feel feminine and I would love it if you would help feminize me to the point I would never look back."

"I'm so happy to see you agree with me. We can be a very loving, girl couple!" Smiled Bonnie.

"But what about you? You don't want to stop having sex do you?" I asked.

"Well, that's the second part of my request. I've done some research online, and I have found several swinger websites that I can register us on presenting us as a wife and her cuckold."

"What's a cuckold?" I asked.

"It's a married partner who engages in sex with others when she wants and she does not have sex at all with her husband, but in your case, it will be me not having sex with my female partner. You won't really be missing anything because you'll be living as a girl, so it's not like you'll be a man who can't fuck his wife." She said softly.

"How is this going to work?" I asked.

"Well, first I want to clean out any male clothing you have and get rid of it. I want it to be impossible for you to wear anything but female clothes. I will prefer that you never wear any female long pants. I want you to wear only dresses or skirts and blouses on an everyday basis. In anticipation of you wanting to do as I say, I went ahead and got you a large supply of male contraceptive that will completely eliminate all the sperm from your body. I also got a large supply of a very safe antihistamine that has a 99% probability of causing you severe impotence. Your days of getting your tiny erections will be over. Won't you love that baby?" She asked.

"I will enjoy not having erections in my panties. The feeling of a hard cock in my panties is not at all appealing to me."

"You see, you're already well on your way to being my full time girlfriend partner." Smiled Bonnie.

"Will we still sleep in the same bed?" I asked.

"Of course we will. You will only be allowed in bed if you have your panties on under your nightgown." She answered.

"I can do that, and having the pressure to please you sexually removed from our relationship will come as a relief to me if I'm being honest."

"Oh good baby. Now take your first two pills and let's start getting rid of your male clothes right now." Said Bonnie.

I took the pills and helped her box up every article of male clothing in the house. We arraigned to have it picked up by a donation truck the next day. We also bought several more dresses and skirts and blouses for me to fill out my wardrobe. After about three weeks of this I was settling nicely into my new role of a full-time girl.

"Have you signed us up on any of the swingers web-sites you talked about before?" I asked.

"Not yet honey. I wanted to be sure it was impossible for you to get an erection, and we have an appointment at the doctor tomorrow to have them take a sperm count from you to make sure you don't have any. I want you as close to being a physical girl as you can be before I invite a real man to spend time with us." Answered Bonnie.

"So we're going to be doing this together?" I asked.

"Absolutely baby. If I find a man I want to have intercourse with I want you in the room watching when he fucks me. I would even like to teach you how to suck on his cock and get it really hard before he enters me so he can slide it inside me as deep as possible."

"Oh wow! This is really going to be something if it happens." I replied.

"It's only going to happen if you are completely incapable of male sexual arousal. Do you think the pills have been taking are doing what we wanted them to do?" Asked Bonnie.

"I haven't felt anything sexual between my legs for over a week now, the tiny softness in the front of my panties feels so natural to me, it's like it should always have been that way. I'll be surprised if I have any kind of sperm count when it is measured tomorrow as I have not missed one pill." I smiled.

"You have easily slipped into the role of a girl as I hoped you would. You wear lovely make-up every day, your lingerie and dresses are so feminine. It's impossible to think of you as anything but a pretty girl Cindy. And I love you for it." Said Bonnie as she leaned in and kissed me on the lips.

The next day at the doctor's office I was completely dressed in a knee length dress with a flare skirt to it and a very pretty slight white petticoat over my panties on underneath. Bonnie went with me to the appointment and sat with me in the exam room. The doctor was aware of the fact that I was working to be a biologically neutered male who wanted to present myself to the world as a girl. She was very kind and understanding and when she checked my sperm level she found it to be completely undetectable. She also looked at my ball sack and felt my testicles in my panties. She finished her quick check-up by putting her hands on my breasts.

"Cindy honey, the results of our in office lab shows you have no sperm at all in your body and your body is not producing any at this time." Said the doctor.

"That is very good news to hear doctor. Thank you for such quick results." I smiled.

"What usually happens as a by-product of this kind of lab result is that your body is also producing a very small amount of semen. Your body senses that semen is not needed because there is no sperm and it shuts down to a level that is very small. Have you ejaculated any white semen recently?" Asked the doctor.

"I haven't ejaculated, or even had the urge to ejaculate for close to nine months now. I don't even think about it." I answered.

"Then I think it is fair to say you have reached your goal of being chemically neutered. It would be impossible for you to perform the act of sexual intercourse as a male. What about erections? Have you had any of those lately?" Asked the doctor.

"The last time I felt even a slight plumpness between my legs was almost five months ago. Since that time there has been nothing." Was my answer.

"Then under medical terms you are classified as fully impotent as a male. I think that's what you and Bonnie were trying to achieve." Said the doctor.

"It is exactly what we wanted to achieve." I smiled.

"And Cindy is in perfect health otherwise, isn't she?" Asked Bonnie.

"She certainly is. My exam shows me her testicles have shrunken by about 50% since she was last here. It should mean her body is barely producing testosterone. Her natural testosterone levels were low to begin with and now this decrease, along with an increase in natural estrogen is starting to give her many female traits. I noticed a very small increase in her breast size. You may feel your breasts aching a little going forward Cindy, but that is a natural part of them growing. Without estrogen supplements, her breast growth will be very slow and it would be lucky for her if they grew to an A cup size. I would keep her doing what you are doing and her physical condition should be just fine, but I suggest check-ups at six months just to be sure. Sexually she will need to learn to enjoy intimacy as a girl, which is something I know you want to do." Said the doctor.

"I most certainly do, and thank you doctor for all your help." I replied.

Bonnie and I were very happy living together as two girls. With my male sex organs neutered I was relieved not to have male sex urges. I worked every day to perfect my female appearance and was very successful projecting myself as a pretty "girl-next-door." It was about three months after this that Bonnie came to me with her next request.

"Cindy baby, I'd like to teach you how to use your tongue and lips to lick and suck on my pussy and clit. Can I count on you to want to learn?"

"I think I can learn and I would be very interested to know what pleasures you the most." Was my answer.

That same night when we were in bed, Bonnie lifted her nightgown up and had me get between her legs with me still in my panties and nightgown. She instructed me what to do next.

"Put your mouth on my pussy lips and slide your tongue inside me."

I did as she asked and found myself enjoying the warm wet feel of her cunt.

"Now gently put your lips on my clit and slowly suck on it bringing it into a full erection." Was her next instruction.

I did as requested and lightly pulled Bonnie's clit up by licking and sucking on it. Her clit was almost a full inch in length as I heard her breathing slow down and get deeper.

"Put your face back into my pussy and let your nose bump into my clit. You're really good at this and I'm about to cum." Moaned Bonnie.

My tongue was now deep into her cunt and my nose was touching her clit as she grabbed me by my shoulder length hair and she began to convulse in a very physical orgasm. She pushed me deeper into her pussy lips and then let out a low scream as she came. My mouth was soaked in her juices.

"Oh my God! You are such a good pussy licker! I had no idea you were this good. We're going to be doing a lot more of this I can assure you." Said Bonnie out of breath.

Over the next couple of months Bonnie had me licking and sucking her pussy at least five times a week. Part of her training me to do this involved getting my tongue deeper and deeper into her cunt and curling my tongue to lick out her juices. I really enjoyed the experience and was only too happy to do it. My lifeless little penis was totally soft and tiny in my panties while the nipples on my breasts stood up straight and became larger the longer I was between her legs. Bonnie's clit was really fun to suck on and pull on with my lips and I loved having it stand up straight out from under its hood. We were settling into a wonderful sex life together.

I had been living as a girl for at least a year and had really perfected my female appearance when Bonnie told me about the next step she wanted to take in our marriage.

"Cindy honey, you have become a very pretty girl and a wonderful lover for me. So I want to move forward with what I told you about a year ago. I have been listing our photos on a swinger web-site clearly stating you and I are married and you are my cuckold. I've listed that you and I do not have male/female sexual intercourse and haven't for over two years."