Brother-In-Law Makes Three

My wife and I were married when we were both 25 years old. My wife's name is Rachel, my name is Matt. Together in the beginning we enjoyed an active sex life. Rachel had told me before we were married that she had been pregnant and had an abortion when she was only 19 years old, but this did not matter to me in the least. I liked the fact she was sexually experienced.

It was around our first wedding anniversary that we sat together naked on the bed and Rachel wanted to talk about sex.

"Let's tell each other our wildest sexual thoughts." Smiled Rachel.

I was a little surprised at her forwardness, but I found it exciting.

"Do you want me to go first?" I asked.

"Yes, tell me what really turns you on!" She laughed.

"Well, okay, I hope you don't think this is weird. I get really turned on wearing women's lingerie. I love wearing bras, panties, and slips." I said all at once.

"Oh wow! I can't believe you said that! I always wanted to dress a guy as a girl and then have sex with him!" Smiled Rachel.

"Are you serious? You're not just saying this?" I asked.

"I'm very serious. How do you feel about putting on make-up?" Asked Rachel.

"I've never really tried it before." I answered.

"What if I helped you dress as a girl fully and we went out together as two girls?"

"That sounds really kinky. It sounds like fun. Do you think we'd be safe?" I asked.

"Of course we will. I'll make you into a really pretty girl and we'll go to the shopping mall and window shop." Said Rachel.

"That sounds fun, but you haven't told me what your turn on is."

"My turn on is what you like. I can't believe we are so lucky to find one another. I dream of having sex with a pretty girl who has a big erection between her legs!" Smiled Rachel.

"Oh wow. Have you even done that before?" I asked.

"Well, here is the rest of my wild sex experience. I caught my brother, who you know is just a year older than me, wearing our mother's panties, bra, and a half-slip. He was 20 years old and I had just turned 19 at the time. He begged me not to tell anyone and I agreed to his request if he would have sex with me and take my virginity." Said Rachel looking down.

"And you did this? You let your brother fuck you?" I said in amazement.

"Well it wasn't his idea, I was the aggressor, and losing my virginity to my own brother just seemed like something I wanted to do."

"So he was your first?" I asked.

"He was. We waited until we were alone in the house and we knew our parents wouldn't return for a while, and he went to my mother's lingerie drawer and got a pair of her panties and a satin and lace bra and a pretty half-slip with lots of lace on the hem. He let me watch him strip naked and then put on the lingerie. I let him watch me strip naked and put on my little girl baby-doll nighty. We got into bed together and shared our first tongue kiss as I reached into his panties and began stroking his erection."

"Was he also a virgin?" I asked.

"No. He wasn't, but he was very gentle with me and both of us were so turned on my pussy was soaking wet and he was long and hard. I guided him inside me easily and it did not hurt at all. He ejaculated very quickly with a huge load of semen deep inside me. That's all it took, one fuck and I got pregnant." Explained Rachel.

"So that is why you terminated your pregnancy because it was your brother who got you pregnant?" I asked.

"That was why." She answered.

"Was that the only time you had sex with him?" I asked.

"We were more careful and I wanted him because it felt so good. We had sex a handful more times, but then we stopped. You and he are the only two men I have ever had sex with." Said Rachel.

"So it has been a long time ago?" I asked.

"Of course baby, let's not talk about that now, let's talk about getting you your own lingerie. I think you should start wearing a bra, panties, and a slip every day from now on." Smiled Rachel.

"I have to admit, I'd love to do that! I like to wear ultra-feminine, "retro" lingerie. I love lots of lace and lots of nylon." I smiled.

"Ohhh, that sounds sexy! Of course we can find that for you honey." Said Rachel.

Over the next few days Rachel and I looked at all types of websites and found a large trove of vintage, very feminine, and very pretty lingerie. Rachel took it upon herself to dispose of all my male underwear. She cleaned out our dresser of all I had and as the pretty lingerie we ordered began arriving she filled my dresser drawer with my new female clothing. She only allowed me to put on full cut panties.

"Matt honey; I'm going to want you to wear a training bra and panties every day from now on. Can you do that for me?" Asked Rachel.

"I can and I will." Was my answer.

"And when we have time to ourselves, I'm going to teach you how to put on make-up and a wig and I'm going to get you some dresses so we can show you how pretty you can look." Continued Rachel.

"You have no idea how exciting this is for me. I've always wanted to see how feminine I could look, and to have my wife help me do this is too good to be true." I smiled.

It was just a couple of days later that Rachel and I had our time together and she had brought home a wig and a full set of make-up for me. She picked out a perfect shade of lip gloss for me along with eyelashes and mascara that when she applied them was dramatic in its effect. I was in just my bra and panties when she began her work on me and when she was finished with my face foundation and eyeliner and eye shadow she helped me pull my wig into position and then she had me look in the mirror. I was shocked. A perfectly natural and normal girl looked back at me from the mirror! To my surprise, my nipples grew large in my bra and my penis pulled back into my body. In addition to looking like a girl, I was beginning to feel deep down that I was a girl.

"Oh my God! You are so pretty! I had no idea I could make you into such a pretty girl! You really are beautiful." Gushed Rachel as she looked me over.

"I'm a little surprised myself, and a little excited by what I see." I smiled.

"Well let's not stop here. I've got you some stockings and a garter belt. Put the garter belt on over your panties and I'll show you how to slide on your stockings and attach them. After that, I want you in a full slip and then I'm going to pick out a dress for you to wear the rest of the day." Smiled Rachel.

With my stockings in place and attached to my garter belt I put on the pink dress with the white polka dots on it that Rachel picked out. I was more than passable as a pretty girl and I looked more feminine than my wife at this moment.

"I'm going to take you to the movies this evening. We'll be on a date as two girls." Said Rachel.

That night was my first night out in public fully feminized and I passed without any trouble. In the theatre during the movie Rachel and I held hands and about midway through the movie Rachel slid her hand down to the hem of my dress and then slowly lifted my dress attempting to run her hand up my stockings to my garter belt. I quietly pushed her hand back down and whispered to her to stop. She did as I asked and smiled. I could see why she was the aggressor with her brother. My wife liked being aggressive about sex. I felt myself sliding deeper into my role as a female and it was a surprise to me, but I found the idea of another girl making sexual advances toward me to be something I did not want. On the way home in the car Rachel asked;

"How come you brushed me away when I tried to put my hand under your dress?"

"I don't know. I just didn't want to create a scene in the theatre." I answered.

"I wasn't going to create a scene. I just wanted to feel the satin and lace of your garter belt and flick my fingers at the crotch of your panties to feel how hard your cock was getting." She responded.

"I wasn't hard. I was neatly tucked back in my panties. Good girls don't have cocks in their panties." I smiled.

"Well, when we get home, I'm going to take my good girl to bed and we'll see about that." She sneered.

When we got home Rachel asked me to wear my very feminine and pretty which baby doll nighty with the big full cut bloomers. She wanted me to keep my stockings and garter belt on under my nighty. Rachel put on a full length nylon and lace pink nightgown without any panties on. She looked very sexy.

"Okay, good girl. Let's see how good you are." Said Rachel as she climbed into our bed and held up the covers.

I got into bed with her and we were lying face to face as she reached out to kiss me with her tongue sliding into my mouth. I found myself quietly repeating "I am a girl, I am a girl" in my mind. At that moment I experienced a sensation that I never had before. I felt what I was doing was very wrong. I am a girl and I am in bed with another girl. Nothing about Rachel putting her tongue in my mouth and running her hands over my baby doll felt sexy. The feeling I was having was shocking. I was in bed with my wife who was overly sexed up and I had no sexual thoughts toward her. I really didn't know what to do. Rachel rolled over on top of me as she lifted her nightgown. My fully shaved body was under her in my baby doll and garter belt and stockings as she pulled my baby doll bloomers completely off and reached for my cock which was fully limp and very short.

"What's happened to your cock?" Said Rachel in a surprised voice and she started stroking it to get it to respond.

"I, I... Don't know. I'm having trouble getting any kind of erection started." I stammered.

"And why would that be? I'm your wife!" Said Rachel loudly.

"Well maybe it's because I have gone so deeply into being a girl. It's a little bit wrong for me to be in bed with another girl." I said softly.

"I'm not another girl, I'm your wife and you need to get hard for me. I want you to fuck me and do it now." Said Rachel loudly.

"I'm sorry honey, I just can't do it." I replied.

And I was right. My cock was fully soft and very small. My nipples on the other hand were big and hard but couldn't be seen under my baby doll. Rachel rolled off of me and did not say another word all night.

I continued to wear bra, panties, and a slip on a daily basis and a pretty long nightgown over a pair of panties at night. I began to notice that I wasn't having any night time erections, but I would wake up every morning with very erect nipples. It had been a week since Rachel and I had attempted to have sex when she turned to me one night and said;

"Since you know so much about being a woman, what if you put your mouth on my pussy and eat me out. Maybe I can cum with you doing that. Could you do that for me?"

"I can try." I said.

"Good. Now let's get into bed and I'll spread my legs and you use your tongue on me and make me cum." Directed Rachel.

Rachel's pussy was always fully shaved and she lifted her nightgown and spread her legs. I remained in my nightgown and panties and put my face between her legs. Rachel was right, I did seem to easily know where to find her clit and where to suck on her pussy. I was doing a very good job and she was moaning loudly and I felt her clit get larger and her pussy lips become very wet. On the other hand, I was not having any hint of male sexual arousal. No erection, no desire to ejaculate, nothing. I was a girl eating out another girl. A few minutes into this sex act and Rachel began to experience orgasm. She wiggled and convulsed into my face as she came. Then she did it a second time almost immediately.

"You're right. You're a really good girl who knows how to please a girl. Did you cum in your panties?" She asked.

"No. I still couldn't get hard. Rachel honey, being a sissy is much easier for me than being a husband." I admitted.

"Well, if you can eat me out as good as you did today, maybe we can work something out." She smiled.

"What do you have in mind?" I asked.

"I think I'm going to call my brother. I'm sure he'd like to see what you've become."

"Your brother? Are you sure that is a good idea? He'll think I'm not good enough for his sister." I replied.

"Are you kidding? He loved dressing in our mother's lingerie. He will completely understand where you're coming from. Besides, you know how handsome he can be." She smiled.

"He does have a good body." I agreed.

It was just a few weeks later when Rachel's brother, Joe, came to the house for dinner. I looked at Joe differently now for two reasons; one, I now knew he and my wife had engaged in sexual intercourse more than once and he had gotten her pregnant. Two, I found myself now looking at him as the girl I was and the handsome man he was. I was fully dressed as a girl in my blue satin and lace evening dress that came just below my knees. My breasts were still in my training bra, but one could see I did have two nice curves to my chest.

"Oh my God Matt, you're beautiful!" Said Joe as I opened the door.

"Thank you so much. Rachel has told me about your love of a pretty woman and I'm a little excited you find me beautiful." Was my response.

We were all sharing several adult drinks before dinner and Joe had his eyes on me and every one of my movements. I could tell he was getting an erection in his pants as we all laughed and talked together. Knowing that a man was starting to lust after me was very exciting.

After dinner the three of us were again in the living room and this time Joe sat down on the sofa next to me.

"So Rachel told me about her giving you her virginity." I said in a sultry way.

"Oh yeah. I guess you know how good she is in bed." Replied Joe.

"Well that's were things have taken a bit of a turn...." Said Rachel butting in.

"What do you mean by that?" Asked Joe.

"So, as you can see, Matt is a very pretty girl. And he is now deep into his role as a girl every day. And as a girl, it's making it difficult for him to perform sexually as my husband." Said Rachel.

"He can't fuck you?" Blurted out Joe.

"Well, he hasn't in a long time now." Said Rachel.

"So you are taking this girl thing seriously?" Said Joe to me as he put his hand on my knee over my dress.

"I like being a girl. I want to experience things as a girl, and that includes sex." I said directly as I put my hand into Joe's crotch over his pants. I immediately felt his erection in his pants.

"Would you like to put Joe's erection in your mouth?" Asked Rachel.

"Only if he would like me to." I replied.

"I would love you to. I thought you'd never ask." Said Joe as he stood up and unzipped his pants. As his pants fell to the floor he quickly pushed his boxers down and his more than half erect cock came into view. I felt a jolt of excitement shoot through my body.

"If you two are going to do this, I want to watch." Said Rachel.

"That's cool." Said Joe as I got on my knees in front of his erection preparing for the first time ever to put an erect penis into my mouth.

Rachel stood up to watch us and when she did she started taking off all her clothes. She was fully nude very quickly as she said;

"Go ahead baby; take Joe's cock into your mouth and get him even harder."

I did as she asked flicking my tongue on his cock helmet and holding my hand on the base of his cock. I felt him getting harder very quickly so I began to lick my tongue up and down his shaft and to lick his ball sack. Then I kissed the underside of his cock shaft and gently slid my mouth over the end of his cock. I wiggled my mouth around his shaft and felt him throbbing. I bobbed my head up and down on his cock as he got harder and harder. I was gasping for breath as I did this and for the first time in several weeks I felt my penis having a rock hard erection really quickly in my panties. Since I had not ejaculated for several weeks I felt myself very close to cumming.

"I'm.... I'm going to cum in my panties!" I managed to say.

At that exact moment I felt my cock pumping thick streams of semen into the crotch of my panties and I couldn't stop it. I was twitching between my legs and every time I did another rope of cum shot out of me. Joe's cock was still in my mouth as I almost fainted in delight. Again a rope of cum shot out of me and I felt the hot thick cum piling up in my panties. I had never, ever cum this intensely when I was inside my wife but I was doing it now in my own panties under my dress. My orgasm was quickly interrupted by Rachel and she pulled me back saying;

"So you can cum for a man but not for me you little sissy!? Don't make Joe cum. That's going to be for me tonight. I need a hard cock and I want Joe's inside me right now."

Rachel got on her back on the sofa quickly and spread her legs wide open showing her wet, pink, puffy pussy lips.

"Come to me Joe. Fuck your sister like we did so many times before!" Said Rachel loudly.

Joe pulled back from my mouth and quickly got between Rachel's legs as she pulled his erection into her wet lips. The two of them were tightly copulated as I watched while catching my breath.

"That's the cock I love! Fuck me! Fuck your sister! Oh my God you feel so good inside me!" Shouted Rachel.

Joe pushed again and began to grunt as I had gotten him close to cumming. Joe's crotch began to twitch and it was obvious he was ejaculating into my wife.

"That's it! Cum inside me! Do it! That's how a man fucks a woman! I'm cumming too! We're doing it together! You know how to fuck me! Don't you like watching your wife getting fucked by a real man's cock? This is something I deserve!" Shouted Rachel as her body twitched in pleasure and she looked right at me.

I was watching all of this and found myself wishing I was Rachel and that Joe was fucking me. Instead I felt the entire limp head of my cock covered in hot semen in my panties. I was pleased that my erection had disappeared so quickly and I was fully limp again. I found the feeling of an erection in my panties very disgusting. I was wishing I could ejaculate without having any sort of hardness in my cock.

I was not at all jealous of my wife fucking her brother. I liked seeing her have so much pleasure. I found myself looking at her and me as two close girlfriends. After Joe and Rachel caught their breath, he dressed and they kissed goodnight as he left. I was still fully dressed with my panty filled with semen and Rachel was totally nude. She had me sit down on the sofa with her as she told me the rules moving forward.

"I had forgotten how good a lover my brother is. Did you see the way he fucked me and how I loved it?"

"I did, and you really seemed to be into it." I replied.

"Okay then. Going forward, you and I will stop trying to have intercourse. You know who the boss is here, it's me. So you need to listen to me right now and do everything I say. When I want you to, you will use your mouth on my pussy and my clit. When you sucked and licked me you were pretty good and I orgasmed when you flicked your tongue on my clit. You cannot say no when I ask for it, understand?"

"I understand." I said softly.

"You feel a lot better with me in control and you know it. You know and have seen how I like big hard cocks and we know you can't do that for me anymore. I'm going to tell Joe that I want him to fuck me on a more than regular basis and I want you to be watching us most of the time. Joe's cock is so much bigger than yours, you can never make me feel as good fucking as Joe can make me feel. He fucks me better than you ever will. I'm on the pill now, but I will decide when to stop it, and if he gets me pregnant, this time I will have the baby and you will help me raise it. All you have to do is listen to me, it's really not that difficult. I don't want attention from other men, I only want attention from Joe. Don't think of it as cheating, think of it as I need to be satisfied." She continued.

"I can agree to this with a few conditions." I said directly.

"And what are those?" She asked.

"I want you to help me find a doctor who will start me on hormone therapy. I want to stop having any kind of erections; I don't like having them. I also want to have the hormones help me grow some natural breasts. I still like to ejaculate, but I want to do it fully limp. I can see a day when I would like to have my testicles removed. That will stop my body from producing testosterone and get me further into what I want to be sexually and that is a girl. You have helped to start me down this road and I want you to help me finish things. I don't ever again want to try to have sex as a male. You're right, I'm a sissy." I said confidently.

"Oh wow honey, you are really into this." Said Rachel.

"I am. I'm a girl in my mind already. Sucking on Joe's cock felt so natural to me. Wearing a training bra, panties, and a slip under a dress everyday feels natural to me. I love it that I am so pretty when I am dressed. I don't want to wear male clothing ever again if I can help it. Mentally I am all girl and I want to be one physically as much as I can." I smiled.

"I can agree on that. I'm also going to have lots of foreplay with Joe. I want to elevate our fucking to love making. I'm going to want him to suck on my nipples and play with my breasts. Will that bother you?" Smiled Rachel.

"Only the part where I wish I had breasts as big as yours. That's why I want to start this as soon as possible. I want to physically be a girl as much as I can be."

Both Rachel and I kept our promises to each other. Rachel found a female doctor who she took me to see. Rachel went into the office appointment with me and I was fully dressed for the outing as my pretty girl self. The interview lasted just five minutes as the doctor was surprised that I even needed hormones she said I looked so naturally feminine. We were shown to an exam room and my first injection was quick and easy. I was to start with testosterone blockers and proceed to estrogen injection within the first week followed by monthly injections and monitoring appointments. I did not miss any scheduled appointments.

During the first year of this arraignment Rachel and Joe and I settled into a sexual routine that was pleasing to all three of us. I watched my wife and her brother fuck over one hundred times. I usually sucked on Joe's cock before he and my wife had sex. I had learned how to get him really hard for her. I also learned how to bring him to the edge of ejaculation. While I was licking and sucking on his erection I always kept an eye on the hole in the tip of his penis and felt it with my tongue. If I saw or felt the hole opening up I knew it was time to stop sucking him and turn him over to my wife for insertion into her pussy. I did sometimes stay on him a little too long and a few times I tasted his pre-cum which is a taste I really loved.

I was about 14 months into my injections when I really began to notice true progress. In the first two months of treatments my penis shrunk very quickly. I was forced to pee sitting down every time. Erections were almost non-existent and ejaculations were smaller in size. At the one year mark my ability to shoot out a rope of thick white semen was completely gone. My ejaculations consisted of mostly a clear watery discharge that almost felt to me like I was peeing. When I mentioned this to the doctor she said this was normal as the estrogen was shrinking my prostate and slowly destroying its ability to function and create semen.

I had gotten through the past two months of a somewhat painful growth of my breasts and now at 14 months in I had natural A cup breasts with enlarged areolas and nipples. The doctor told me it would be at least another year for me to grow another cup size. This excited me and I was more than ready to schedule the appointment to remove my testicles. The procedure would be simple and an outpatient one because my balls had shriveled up to next to nothing. My wife Rachel went with me to my pre-op appointment. The doctor asked;

"If you like, it's a very easy thing for me to do with a few extra incisions to make it physically impossible for you to ever have any sort of erections or hardness in what is left of your penis. Would you like me to do this when I remove your little testicles?"

I did not hesitate at all, my answer was an emphatic "Yes, I would like that very much."

"You understand, this will become a permanent change for you, one that cannot be reversed. It's been several months since your body produced any sperm, but once the testicles come out you will never be able to father a child. Not that you would want to." Smiled the doctor.

I looked into my wife's eyes and we held hands as I turned to the doctor and said; "I understand, and I cannot wait to take this next step." I had experienced being more emotional due to the hormones and my eyes watered at this turning point as my dream of never again having an erection or never again having to feel a bulge between my legs was closer than ever. The nurses could not have been nicer to me for the procedure and I was home the same day. Everything returned to normal within a month and I have never, ever regretted having the surgery.

My wife and Joe are regular sex partners and I am with them most all the time. I have gotten very good at sucking Joe's big erections and my wife has even allowed me to bring him to orgasm a few times and to swallow his ejaculation. I adore the taste of his semen and I usually have my own sissy-gasam when I do this. My wife has not gotten pregnant and I'm not sure if is because she is still on birth control pills, or if Joe has been unable to get her pregnant. My scrotum was removed along with my testicles and without any internal sources of testosterone my body has been feminized almost completely. My hips have gotten wider, I have no body hair at all, my breasts are growing from an A cup to a solid B cup. My prostate has been shrunk so small it has become damaged beyond repair. My body produces no semen at all, and that's just perfect. I'm a girl and I love being a girl. I hope the way the three of us are living goes on for a very long time.