My Wife helped Me Become a Girl

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

*****

It's embarrassing to admit, but I was 25 years old the first time I had male/female sexual intercourse.

My virginity was lost on my wedding night to my wife. My wife is almost ten years older than I am. She really liked the fact that I had a history of wearing lingerie and that I had a sincere desire to dress and be a girl.

We met each other working at the same place, a bank in a large downtown high rise. Finding a biological female who was not put off by my desires and who encouraged me to explore my feminine side was for me, incredible luck. But all luck comes with a catch.

My future wife was the aggressor in our relationship and asked me for our first date. I always liked being around her and was anxious to spend time with her outside our work environment. On our first date we had a nice dinner out and then ended up back at her place talking all night. It was as if I had known her my entire life.

By working together we knew about each other in a professional way so our conversation on our first date quickly turned toward our more intimate secrets. We shared our sexual past with each other without any reservation. I felt totally comfortable telling her about my lifelong experience wearing lingerie and dresses and my desire to finally become knowledgeable to do my own make-up the way I wanted to do it, which was in the "girl next door" style. I told her about my large collection of lingerie and how the more nylon and lace my panties, bra, and slip had on them, the more I loved them. I even confessed to her that I wore panties and a slip at the very least under my male clothing as often as I could.

When she heard my story her eyes got really big and she begged me to tell her more leaving out no detail. I told her she had heard my story in great detail and there was not really much more to tell. She asked me if I had ever kissed a male before or had any kind of sexual experience with a male and I said;

"No."

She asked me if I every "wanted" to experience sex with a male and I paused in my answer and feeling the effects of our evening of drinking I said;

"Maybe."

She seemed to exhale and let her guard down as she began to tell me the story of her sexual history. She was the youngest of three children in her family. Her sister, who was the closest to her in age, was ten years older than her. My future wife was the "surprise" of her family as her parents were older than normal when she was born.

Always being around an older female sibling she was introduced to mature sexual situations at an earlier age than most girls. Her sister was 28 when she got married and my wife had turned 18 just a few months before the wedding.

The man who her sister was marrying was a real player. When he was dating her sister and my wife had turned 18, he started leaving my wife envelopes that had sexually explicit stories and pictures in them. Then the next time he saw her he asked if she had read them. Her sister was not aware of this activity and my wife was scared to tell her or their parents what he was doing as it was kinda exciting that an older man found her attractive.

Two weeks before she was going to be a bridesmaid in her sister's wedding, her sister's future husband had put his most recent envelope in her dresser drawer when she was not home. In the package was a very realistic penis dildo of moderate size. At the rehearsal dinner when my wife and he were talking at the side of the room he asked her if she had read his latest present. She said she had and he was going to have to stop this since he was marrying her sister. He said;

"You're right. I'm out of my depth with this and I'll be good and become your brother-in-law as I should."

She thanked him, and everything was fine for the next week. Then, at the reception of the wedding my wife was a little surprised when her new brother-in-law grabbed her butt through her bridesmaid gown in a sexually aggressive way. He smiled at her as she brushed his hand away from her backside saying;

"Stop. Mind your manners."

He took his hand away and said;

"Ohhhhh, you're wearing your full cut white lace panties. I can feel the lace around the leg openings and the waistband. Those are your panties with a large lace panel in front. I've seen them when I put my envelopes to you in your dresser, very nice."

He was right. She had on lots of wedding lingerie under her floor length bridesmaid gown. She was a little surprised that he had memorized the type of panties she had in her dresser but she was also a little excited that he had taken the time to do it.

Her sister and her new husband fucked like rabbits on their honeymoon and it was during the honeymoon that my wife's sister became pregnant. The brother in law kept his promise and left my wife to herself. But seven months after the wedding the sex between him and his very pregnant wife started to decrease. Envelopes with pornographic stories started appearing in my wife's dresser again after her sister and brother in law had visited her house where she lived with her parents.

My wife said nothing to her brother in law, but she enjoyed reading the stories he left for her and she began to experiment with the penis shaped dildo. It was with that dildo that she had her first orgasm.

Both her sister and brother in law worked, and a few months after the baby was born there was a need for babysitting on a daily basis from 9am until about 2pm when the brother in law got home from his early morning work schedule. My wife's sister did not get home until 6pm and it was the time from 2pm to around 5pm that led to what happened next.

My wife's sister turned to her for the baby sitting and my wife agreed. She was almost 19 at the time and did not have a full time job. So every Monday through Friday my wife was to take care of the baby when her sister left for work until her brother in law got home at 2pm. The baby was always down for the afternoon nap at 2pm so there was plenty of "alone time" for my wife and her brother in law.

It was Wednesday of the first week when the brother in law made advances toward my future wife. She told me she resisted a little bit at first, but the thought of what was happening was too exciting to ignore all together.

Every day things progressed a little bit further between the two of them. The first moves involved tongue kissing with my wife's pussy being rubbed through her clothes by the brother in law. She was rubbing his cock through his pants. This progressed to him unzipping his pants and taking out his huge erection. He begged her to kiss it and lick it but she was not so sure. On this one afternoon she was wearing a skirt and his hand was up her leg and touching her panties which gave her away as they were soaking wet with her juices. When his hand touched her drenched panties he said;

"Come on. You know you want to do it. I can feel you do. Just take it into your mouth and swirl your tongue around it."

He was right and she knew it so she placed her mouth on his throbbing cock and used her tongue around the rim of the penis head. He immediately got bigger and with a gasp squirted a load of semen into my wife's mouth. She was so surprised she didn't know what to do but he quickly told her to swallow it. She did and found the taste enjoyable. That session opened the door for both of them.

In the following week my wife was pressed further for full on sexual intercourse. The two of them were naked and she kept feeling the head of her brother in law's cock at the lips of her vagina.

"Let me do it." He said.

"You know you want it. And I do too. No one will ever know."

It took three days before she agreed, but on the third day she grabbed his hard cock and every so slowly guided it into her vagina. She kept thinking it was no different than a tampon as she inserted his organ into her body. That was where she lost her virginity.

For the next two weeks they fucked every afternoon to completion. My wife was totally loaded with her brother in law's sperm. And of course, three weeks after that she found out she was pregnant. Pregnant at just under 19 years old with her brother in law's baby. She said it was a most trying time for her.

When she told her brother in law he was pretty matter of fact about it.

"We've fucked so much and I've filled you so many times with my cum I'm really not surprised." He said.

"I'll pay for you to terminate the pregnancy and we'd better do it quickly so no one will know. Promise me you won't say a word to anyone."

My future wife had the abortion after she had to have some uncomfortable counseling, but she knew it was the right thing to do. It did cause her to develop a rather deep seated caution when it came to sexual relations with other men.

After the abortion she and her brother in law remained sexually active with each other but never again did his penis come near her vagina. Finally, when her sister became pregnant again with her second child, just about a year after the first, my wife called sexual play off with her brother in law. They never again touched one another but they were still at the same holiday celebrations with the family.

I met my wife when she was 34 years old and I was 25. I was completely sexually naïve compared to her as she told me she had been fully sexually active with about eight other guys between her brother in law and meeting me. We dated frequently for about six months. We tongue kissed and rubbed each other's genitals but that was all. She told me she sensed something new in me and she asked that we not engage in sexual intercourse unless we were married.

This was a little surprising to me given her history, but since I was a virgin at 25 I was in no real position to disagree. I asked her;

"Is this a proposal?"

"If you want it to be, then yes. Will you marry me?" She said.

"I would love to" I replied.

From that day on things went very fast. We planned the date for six months in the future and with a week to go before the big day I asked her a big favor.

"I would like to wear bridal lingerie under my tuxedo" I said. A little afraid of what her answer would be. To my delight she said;

"Of course! How much and what kind do you want to wear?"

"Full cut nylon and lace panties. A nylon and lace training bra. A satin and lace garter belt holding up lace top stockings. Plus a nylon and lace half-slip on top of it all. And I want it to all be white, as I am a virgin." I replied.

"That sounds wonderful!" She said. "Will you promise me not to take it off until we are in our wedding bed?"

"I wouldn't dream of it" I said. "In fact, I'd like to put on a honeymoon negligee over it when we are finally alone. Is that OK?"

"It's perfect" she said. "It will be our sexy little secret at the wedding. I only hope you find my bridal lingerie as pretty as yours."

"If you are wearing it, it will be beautiful" I replied.

The wedding ceremony and reception afterwards went perfectly. He sister and brother in law were there and I could see in her brother in law's eyes that he knew he was losing her for good.

When we got to our bridal suite in our hotel that night I was anxious to have my very first experience of sexual intercourse. I knew I was going to let my wife lead the way and I was going to follow her direction. She was wearing a beautiful satin and lace gown and she asked me to unbutton it from behind. I did as she asked and she stepped out of the gown wearing a beautiful petticoat and a gorgeous bra holding her ample breasts and her nipples were standing up straight and engorged in a way I had never seen before.

Now her attention turned to me and she said;

"Let me undress you. You don't want to be wearing that tuxedo do you?"

"I don't at all" I replied.

"But I want you to remember what I have on underneath." I said.

"How could I forget?" She said.

"I want to see you in your lingerie and then I want you to put on your negligee. I'll put mine on too so we can both enjoy each other."

As she unbuttoned my pants and they fell to the floor and she took off my jacket and my shirt I was wearing every bit of lingerie I told her I would and she gasped with delight.

"You did it!" She said.

"I thought you would chicken out, but you did it and I am really turned on by it."

"That's wonderful" I said.

"Let's both put on our negligees and you can teach me how to fuck. I've a feeling you'll be an excellent teacher."

We each got into long white nylon and lace gowns. I had on all white lingerie under my gown and she had a pair of bright pink full cut nylon and lace panties under her petticoat and gown. She led me to the bed and we slid together and began kissing and fondling each other in a way I had never done before. My cock was as hard and as big as I had ever seen it. When my wife put her hand on my penis she quietly said;

"Don't take this the wrong way baby, but your dick is pretty small. Are you sure I'm getting you excited?"

I whispered;

"I've never been more excited and this is the biggest I have ever been with my erection. I told you I have more female sex expressions than I do male and you told me you wanted that."

"You're right, I did" she said. "And your little penis is just what I need after the life I have been through. I'm absolutely going to love teaching you to fuck me. Then, I'm going to show you some sex play that I think you're really going to love. Did you bring any male underwear with us?"

"Just one pair like you told me and you said you wanted to pack it." I replied.

"Good. I made sure I left it out of my packing so you'll begin wearing panties and a bra and slip every day from this day forward." She said in a slightly demanding voice.

"I'd love to" I replied. "Let me feel your pussy touching my cock. I've waited for this for a very long time and I'm not sure I will be able to ejaculate inside you. I may have some kind of medical condition that keeps me from cumming."

"You'll cum my dear" she replied. "I'll make sure of it."

And with that she pulled off her panties leaving her nightgown and petticoat on. She laid on her back, spread her legs, and pulled up both of her garments to reveal her pussy which was soaking wet.

"Now get between my legs" she ordered. "Let me grab your little cock and guide it into my cunt."

With that she pulled my little erection toward her and she slid my organ into her waiting lips without any effort. Our pubic bones came together and she said;

"Now slowly pull back and push forward without falling out of me" she instructed.

I did as she directed. Slowly in and out of her pussy with my rock hard tiny cock. It was after about the third push into her that I said;

"I feel like I'm going to have to pee!"

"You're not going to pee" she said, "you're going to cum. I knew you could do it."

With that I lost my breath and at the same time felt my groin spasm as I could feel my semen squirt out of my little dick again and again. My wife just smiled looking up at me.

"That's right" she said. "You're cumming in your wife. Keep filling my insides with all you have to give me."

I was relieved that I could in fact cum. I was just large enough to be able to get inside my wife's pussy lips. She had rather large lips on her vagina and they were very warm, soft, and wet. As we calmed down she asked me;

"Do you like fucking me?"

"I love it" I replied.

My wife said; "Well let's do it again tonight now that you have learned how to do it. I like the fact that your penis is so tiny. I really did not like a big fat cock trying to get inside me. It made me feel dirty and uncomfortable. You and I are a perfect couple when it comes to sex and I want to be your sexual teacher."

"I'm so glad we found each other." I said.

During the next five nights we had intercourse several times. My tiny cock came every time she told me to even though it was only four inches long fully erect.

At the end of our first honeymoon week my wife said;

"You know, there are many ways you can help me orgasm. You don't always have to stick your little cock inside me. Have you ever seen girl on girl porn?"

"I've heard about it but never seen it." I said.

"Let me show you some of my favorite clips." My wife said.

And with that she pulled out a DVD and put it in the player in our bridal suite. The first scene showed two girls on a bed both wearing panties and rubbing their pussies together. They were moaning loudly. The girl on the top removed the panties from the girl on the bottom. With a few more rubs of her pussy with just one girl in panties the moans got louder. Then the girl on top took off her panties and her pussy lips were very wet and very puffy. They were so puffy they looked almost as large as my tiny limp cock. As the lips of their naked cunts rubbed together both girls moaned even louder and one of them had a very physical orgasm. You could see her lips open up wider as she convulsed between her legs.

"Isn't that a turn on?" Asked my wife.

"It really is." I replied.

"Now you have a little penis between your legs so we can't do exactly that, but you can use your mouth and your tongue on my pussy and I will really get off on the feeling. Will you let me show you what to do?" She asked.

"I can't wait." I said.

"Great! Let me take off my panties and pull up my nightgown in front and lay on my back with my legs spread. Then I want you to put your mouth between my legs and do as I tell you."

My wife was very soft but pointed with her directions. I kneeled between her wide spread legs and lowered my mouth to her cleanly shaven and already glistening vaginal lips.

"That's right" she said. "Now stick out your tongue and insert it inside of me. At the top of my vagina lips you'll feel a bump that is getting bigger right now. That is my clit, and I want you to lick it with your tongue and then gently suck on it with your lips seeing how big you can make it get."

It was getting difficult for her to talk as she was gasping for breath as she instructed me in how to suck her to orgasm.

"That's perfect, keep sucking and using your tongue." She said.

As I had her clit in my mouth I could really feel it getting bigger and bigger the more I tongued and sucked it. It felt like a small pinky finger in my mouth.

"Suck me baby. Suck me as hard as you can." She instructed.

As I did this her legs squeezed against my head and she let out a very loud gasping scream while saying;

"I am cumming, I'm cumming so hard. I've never cum like this before! You are my perfect lover."

The lips between her legs were sopping wet. I licked at all her juices with my tongue and swallowed as much as I could. I enjoyed making my wife so happy. I took a second to notice that while all this was happening, my tiny cock did not get hard, it did not get bigger, it did not leak cum. It actually shrunk up and pulled itself and my tiny ball lump under it back into my body. It was a very erotic feeling. I shared this experience with my wife when she calmed down and she said;

"That's fantastic! Your body is reacting to sex like a female. You love wearing lingerie and doing your make-up. I think we can really let you fulfill a dream and be a girl on the outside but at the same time letting me pull on your tiny dick when I want to have you squirt inside me. Is that something you would want to do with me?"

I couldn't believe what I was hearing it was so exciting.

"I'd really love to try that." I said. "When can we start?"

"I've got a special present for you" she said. "Let me get it from my suitcase."

She returned to our bed and told me to take off my panties under my nightgown. I had shaved my entire body clean for the honeymoon so my little cock lay limp between my totally cleaned crotch. With a quick and simple motion my wife slid a metal adjustable ring around the back of my little ball lump. She quickly inserted my little penis into a form fitting tube and she snapped the two devices together. I felt the device clamp between my legs and in an instant she placed a small padlock on the top of the device.