Wife & Brother-In-Law Make Me A Girl

I was a virgin when I met the girl who would become my wife. She was much more experienced at sex than I was and was not a virgin. Her name is Holly and my name is Tom. We were both in our early 20's when we met and we got married when we were around 25 years old. I took a job in a company run by my wife's father and he gave me preferential treatment since I was married to his youngest daughter.

I had not shared with my wife the sexual pleasure I got when I was younger of dressing as a girl. I started wearing my mother's lingerie when I was 18 and she soon found out but instead of being mad, she encouraged me and helped me to fulfill my fantasy. My mother helped me dress completely as a girl with full make-up, a wig, a dress and all necessary lingerie with full sized breast forms in my bra. When we looked in the mirror, I was a very pretty young girl. My mother wanted to take photos and she took hundreds. Photos of me fully dressed and in various stages of undress all the way down to just my bra and panties. These photos were in a special album that I kept hidden.

My wife, Holly, also had an interesting sex life when she was younger, which she was very open about before we were married. Holly was the youngest of three children and probably a mistake. Her oldest brother was 15 years older than her and her older sister was eight years older than her. It was her older sister's husband, Bob, who introduced Holly to sex. On Holly's 18^th birthday, her brother in-law Bob, privately gave her an X-Rated comic book depicting several sexual situations. He told her not to tell anyone about the comic book and to ask him any questions she had. She was a little embarrassed, but she read the book anyway.

Holly's brother-in-law Bob was a pharmaceutical rep whose time was his own as he visited doctor's offices all day selling them different kinds of legal drugs. Holly's sister, who had been married to Bob for eight years, worked full time in a local bank. This type of schedule meant Bob was free to do as he pleased and he set his sights on Holly as a sexual partner. At first she resisted his advances, but as he kept suggesting to her they get together, she saw his interest as exciting and she agreed to meet with him in the middle of the day at his house.

Holly was 19 years old and Bob close to 30. After a first meeting where nothing much happened but some deep tongue kissing, the two of them began to get together at least twice a week. It wasn't long before both of them were fully naked with each other in bed. Bob taught Holly how to suck on his erect cock and how to swallow his semen when he ejaculated. Holly let Bob suck on her nipples and she let him lick her pussy as he gave her the first orgasm she had ever experienced. Bob was always pressuring Holly to have full blown intercourse but she always said "no." Bob would put the head of his hard cock on her wet pussy lips and beg her to let him inside her.

After two or three months of Bob's advances, Holly gave in and she guided his rock hard erection inside her pussy and she gave him her virginity. Bob fucked her to a shattering orgasm and he ejaculated deep inside her with rope after rope of semen and sperm. After that session, both Holly and Bob fucked at least twice a week using only the rhythm method to prevent Holly from becoming pregnant. They were lucky as she never became pregnant and Bob's wife never knew they were fucking on such a regular schedule. About a month or two before Holly and I met she had ended things with Bob as he seemed to want more and more bizarre sex acts with her that she felt went too far.

Holly and I engaged in full sexual intercourse several times before our wedding day and after we were married we settled into a less than active sex life; having full intercourse only a couple of times a month. Around our fifth wedding anniversary I was taken by surprise by what I found one afternoon in my own bedroom.

I came home unexpectedly around noon time and heard moans and sighs coming from my wife and my bedroom. I walked to the bedroom door and saw my wife Holly, and her sister's husband, Bob, fully engaged in sexual intercourse. Holly was wearing a beautiful white teddy with loads of nylon and lace and a gap in the crotch that allowed Bob to fully copulate with her without the need for her to take it off. She had never worn something so feminine and beautiful when we were fucking, so the sight really surprised me. Bob was fully nude as my wife was on top of him riding up and down on his long, hard cock.

"Am I interrupting something?" I said loud enough to be heard.

The two of them quickly turned and looked at me as Bob started ejaculating and could not stop. Holly pushed her pussy all the way down on Bob's cock as it was obvious he was shooting hot semen deep inside her.

"Oh my God...Oh my God...You are so hot!" Gasped Holly as she began to orgasm.

"And you are so tight! I just love your pussy!" Gasped Bob as he kept twitching his cock to empty every last drop of sperm he had.

"How long has this been going on?" I asked again a little louder.

As the two of them caught their breath from what was a very physical sex act my wife turned to me and said;

"Oh don't act so surprised...You knew Bob and I had gone all the way before. He called me last week and I said it would be okay for him to come by."

"Okay?! I'm your husband! He's your sister's husband! I could ruin both of you by telling her." I said loudly.

As Bob's cock began to soften it slipped out of Holly's pussy. She swung he legs off of Bob and looked at me saying;

"You could...But you won't, because I found something a couple of weeks ago, and you are going to listen to me, or I'm going to ruin you!"

"And what did you find?" I replied.

"Your girly photo album...Plus your stash of vintage lingerie. If my father new you were the kind of 'man' who dressed as a woman...He'd fire you on the spot. And if I told your friends what you did, you'd be ruined way more than I would." Said Holly with a sly smile.

I knew she was right. She and Bob had me where they wanted. She showed Bob my photo album and my trunk of lingerie. I had been caught red handed. What began to happen next was a bit of a surprise. I began to get an erection looking at the two of them and thinking about my situation.

"So what are we going to do with our little girl here?" Asked Bob.

"Why don't we have her sit in a chair at the bottom of the bed." Answered Holly.

"And then what?" Asked Bob.

"I'll show you. Just do what I tell you. Tom...sit in the chair facing us and take off your shoes and socks." Ordered Holly.

I did as she asked, not having much of a choice. Holly went over to the dresser and pulled open a drawer to an area I had never seen before and produced a pair of locking handcuffs.

"Put your hands behind the back of the chair my sweetie. Here Bob...Lock these in place on Tom." Directed Holly.

As Bob did this to me I felt my cock twitch again with delight.

"Now unbuckle his pants and pull them off along with his underwear." Said Holly.

As Bob did this I was totally nude from the waist down and showing my erect penis. I was not in Bob's league when it came to length and girth. He had a much more manly cock than I did.

"That's perfect...Now let's buckle his legs to the chair and then get his shirt off so he is totally nude." Ordered Holly.

Again, my wife produced a pair of leather cuffs that came from her dresser in a place I never knew she had. Bob tightly buckled my legs to the chair and unlocked the cuffs as my wife unbuttoned my shirt and pulled it off. I was completely nude and she had Bob again locked my hands behind me and to the chair so I could not move from where I was.

"Bob honey, what do you think of my little sissy's cock?" Asked Holly.

"It's not that big honey. I guess that's why your pussy felt so tight on me when we fucked." Answered Bob.

"That's very true. I forgot how good your man sized penis felt deep inside me." Answered my wife.

"And you felt so good to me too baby!" Smiled Bob.

"Do you think our little sissy here is going to tell anyone about us?" Asked Holly.

"I don't know." Answered Bob.

"What about it, my sissy husband, are you going to say anything to anyone?" Asked Holly.

"Well no...Not really, I mean, you seem to have all the cards." I stammered.

"I do...That's right my sissy. But Bob, we can't have sissy here making noise while we fuck. I think my sissy needs something to keep him quiet." Said Holly as she again went to her dresser and came out with one of those balls attached to a mouth gag. She bent over and pushed the ball into my mouth and then got behind me to tie the gag tightly. After she did this she leaned into my ear and said;

"That's my good little sissy. Now you watch Bob and me fuck again and he'll show you how a real man fucks a good girl like me....And oh, by the way, you and I are going to be taking a break from having sex. I only want Bob's big cock inside me for a while. I'll let you know when and if you can fuck me again. Do you understand me?"

I nodded my head in the affirmative and Holly got back on her knees on the bed. Her pussy was still oozing white semen from the load Bob had shot inside her. My cock was still at full erection and I could see Bob was beginning to get hard again.

"Bob baby. Get the paddle and teach my sissy a lesson that it's not nice to have an erection when she's watching her wife fuck." Sneered Holly.

Bob went into the dresser drawer where Holly had been and seemed to know his way around the drawer of playthings. He pulled out a wooden paddle, the kind you find with a small ball on a rubber band attached. The ball and rubber band had been removed and the wooden paddle was all that was left.

"Is this what you mean?" Asked Bob.

"Yes, that's it honey. My sissy has an erection, such as it is...I need you to teach her that she needs to be fully limp when she watches us fuck. It would be a real turn-off for me if I saw my sissy's watery cum leaking out of the tip of her cock while you were filling me with your hot, thick, semen and sperm." Sighed Holly.

"You want me to paddle it soft?" Asked Bob.

"Yes. That's right." She replied.

My eyes got really big and I began to try and say something but all I could do was groan. I tried to move away but I was completely naked and tied really tightly to the chair. I immediately tried to lose my erection as fast as I could, but it was not fast enough. Bob put the wood of the paddle on the head of my erection and smiled at me.

"This is going to hurt a little you fucking sissy." Said Bob as he quickly pulled the paddle back and gave my cock a quick smack on the head. The pain was intense.

"You fucking little sissy...My sister-in-law needs to be fucked by a real man's cock. She has been complaining to me about your little dick for almost a year. And you call this hard?!" Sneered Bob

Quickly he smacked the side of my erection and this time it was much harder than before. I felt myself immediately starting to go limp and I secretly prayed my cock would shrink out of sight. I was getting soft very fast, thankfully.

"He's going limp Bob. That's enough. Come onto the bed with me and let's show Tom what a really good fuck looks like." Said Holly.

Bob climbed on the bed and was on his knees as his semi erect cock began to get harder. Even semi erect Bob was almost twice the size of me fully hard. Holly was on her knees on the bed too and as she leaned over to take Bob's cock into her mouth I could see the bright white semen Bob had shot into my wife earlier running down her legs as it oozed out of her pussy lips. Holly was looking at me tied and gaged at the foot of the bed as she used her mouth on Bob's huge cock. She pulled off for a second and said to me;

"Now don't you even think of getting hard my little sissy. If you do, I'll have Bob give you another paddling on your sissy clit. Watch us carefully and learn how real men fuck their women. Bob and I have lots of practice with each other doing this and my sister has no idea we are such good lovers."

Holly put Bob's hard cock back in her mouth as I could tell her tongue was lapping around it and she was lightly sucking on his huge erection. She pulled off of it and said;

"Ok Bob honey, it's time for you to fuck me. And this time let's make sure our sissy sees what you are doing to my pussy. Let's give her a good view."

Holly turned herself in my direction so I had a clear view of her cunt lips that were fully engorged and dripping with semen. Bob pushed his hard erection slowly into her pussy and I had a very clear view of him penetrating my wife's vaginal lips. Holly's cunt lips looked as if they were reaching out to Bob's dick and pulling it deeper inside of her. Very quickly the two of them were firmly mated together with their pubic bones touching. Bob did not begin to thrust in and out instead he began a deep and long tongue kiss with Holly as both of them twitched their butt cheeks as they were tightly copulated. Still on their knees and joined at the genitals they tongue kissed for at least three or four minutes. Then, while still joined at the cock and pussy they rolled onto their side as Bob began to thrust in and out of my wife.

"Oh dear God! This is so good! I had no idea I missed you so much!" Screamed Holly.

"And you are so tight baby! You feel wonderful! It's clear you have not been stretched out like this in a long time." Sighed Bob as he pounded in and out.

"Sissy cock is not in the same league with you sweetheart. My God your cock feels wonderful. Cum for Holly...Cum deep inside me now...Fill me with your hot seed!" Holly's eyes rolled back in her head as she orgasmed.

"Here you go baby! A fresh load for your cunt! Oh my God! I'm cumming so hard!" Grunted Bob as his pelvis began to jerk, and it was obvious he was shooting rope after rope of semen deep inside my wife. The two of them fell together and began a deep and long tongue kiss as I struggled to keep my penis limp as I sat at the foot of the bed tied naked to a chair with a ball gag in my mouth.

"Oh wow! Oh my God! I had really forgotten how much I loved fucking you!" Sighed Holly as she looked into Bob's eyes.

"You are my favorite little girl to fuck baby!" Sighed Bob.

"Don't you think it would be okay if we started having intercourse on a regular schedule again?" Asked Holly.

"I'll make sure your sister never knows and I'll always make time for you sweetheart." Answered Bob.

"Then let's have Wednesday at noon be our day and we will meet here every week." Said my wife.

"Agreed." Said Bob.

"Now, what are we going to do with my little sissy?" Asked Holly.

"What would you like to do? It looks to me you can do whatever you want." Replied Bob.

I was still tied and gaged as Holly came to the edge of the bed in front of me still wearing her white nylon and lace crotchless teddy. Her pussy was dripping with bright white semen as Bob had filled her full during their two fuck sessions. Bob went into the other room and put on his clothes. Holly put her finger under my chin and lifted my head to look her straight in the eyes and said;

"You want to dress and act like a girl don't you?"

I could only nod my head, but I gently nodded "yes."

"And during the few times you and I fuck, you really don't like being the male, do you?"

I nodded my head in agreement.

"Bob really knows how to be a male when it comes to fucking a girl. And you know, Bob has a complete suitcase of medicines in his car. I can have Bob help you become what you want to be."

My eyes widened as Holly looked down at my limp little penis.

"Bob...What do you have in your pharmaceutical case that can we can use to help Tom become the girl of his dreams?" Shouted Holly into the other room.

"Well...Let's see...I have estrogen injections if that's what you mean. I also have some things that are stronger." Answered Bob.

"That's exactly what I mean. Go to the car and get them. It's time to turn Tom into a girl." Said Holly looking straight into my eyes.

My eyes opened very wide as a bit of panic came over me and all I could do was grunt with the gag in my mouth and turn my head left and right.

"Oh come on now...You know this is what you want. I want you to stop wearing male underwear and I want you in bra, panties, and a slip every day. You can wear your male outer clothes, but you need to only have lingerie underneath. When you get home from work I want you to change into dresses and sleep only in nightgowns. You're going to be my good little girl." Smiled Holly.

"Holly honey...If I start the estrogen injections we'll need to inject him at least once a week or there could be unhealthy side-effects. And He'll need to take a daily pill between injections." Said Bob.

"He can do that. We'll have him show up here every Wednesday when we get together to fuck. He can watch us and then get his injection. If he doesn't he will have some health problems." Said Holly.

"And the testosterone blocker I have is in the form of an injection that needs to go directly into the scrotum. For the first couple of weeks he'll need to also take a pill a day between injections." Said Bob.

My eyes got as big as could be, but I was helpless being tied so tightly and being completely naked.

"Bob...Get the injections and the pills and start Tom on the road to becoming a girl. It's what he wants and it's what I want for him. Plus it will give all of us a reason to stay quiet about what we are doing each week. Don't you agree my new little girl?" Smiled Holly.

I had no choice but to nod my head 'yes."

Bob returned with two syringes and two bottles of pills. He quickly rubbed a cotton swab of alcohol on my naked butt cheek and injected me with my first dose of estrogen. The second syringe took a little more time as he rubbed a cotton swab with alcohol on the side of my scrotum near my body. He then slowly inserted the needle and began to inject me with testosterone blocker. It seemed like it took forever for the injection as I grunted through my gag.

"There you go honey. We're going to slowly turn you into a girl, both mentally and physically. Bob baby, what should the immediate effects be?" Asked Holly.

"He should be done with having erections. I don't think he could fuck you even if you wanted him to. He needs to take the pills here on a daily basis and never miss taking them. In a couple of weeks he can stop the testosterone blockers and I'll have to give his ball sack one more injection next week in addition to an injection of estrogen. I'll need to give him estrogen injections every week for about three months. Then he can just keep taking the pills."

"Oh that sounds like a workable plan. All of us can get together every Wednesday. Next week I'm going to wear the wedding night baby doll white nighty I wore the first time you and I had sex. I've never let Tom see it so it will be a first for him." Smiled Holly.

"You know how I like you wearing pretty lingerie." Answered Bob.

"I do baby. I'm going to buy some new outfits for you to fuck me in. I'll bet my sister does none of this for you."

"You got that right." Replied Bob.

"You know Bob...My sister has a yearly business trip she takes with her company. It's four days and it happens sometime in June. Maybe you and I could get away for a couple of those days and go to a romantic hotel. We could pretend it was our honeymoon and fuck like rabbits." Said Holly.

"I would love that! I know just the place. What about Tom?" Asked Bob.

"He'll stay here at the house. In another six months when June comes around he should be starting to show some of the effects of his injections and pills. And he should have no ability to have any kind of sex with a girl by then so he won't miss anything." Reassured Holly.