So Does This Make Me A Woman: Pt 1

by Bob Watergate (Missouri)

So many men share the story of their wives doing them in and forcing them to take hormones or tricking them into taking hormones. For me it was actually my brother that tricked me, well at least in the beginning!

Terry almost raised me since we lost our father due to cancer so our mother was working all the time just to acquire all the money we needed! Terry took care of the house doing all the cleaning, cooking and laundry!

I can remember from an early age hearing Terry telling me to set down to pee, according to him so I wouldn’t get my pee on the floor causing a mess to clean up. Next I guess I remember asking him why we had to sleep together and he told me it saved the number of sheets he had to wash!

It wasn’t till after High School when our Mother was killed by a hit and run driver! She left us the house and if not for her little bit of insurance we really would have been in trouble keeping it up!

I remember being so sad and crying all the time, especially at night! Since we had slept together when we were younger, I agreed to climb into Terry’s bed that night. What I first thought was strange was I was awaken with Terry playing with my nipples! I had already seen a porn magazine and questioned why a man would want to play with another man’s nipples! Since we continued to sleep together, things continued to change but ever so slowly!

“Terry, I need some new underwear, mine are worn and even torn in places!” I shared. He said money was tight and just to shut up about that little problem! Within days I started to notice there were panties in my drawer and all of my worn underwear was gone!

“Terry why are there panties in my underwear drawer?” I asked him.

“Look squirt, I told you money is tight and since you are the same size as Mom I got some of her panties out and put them in for you to wear!” He told me. “Listen Bob we are both going to have to make some changes to get by in the months and years and I need your help, please!”

“Sure ok Terry, just tell me what I can do to help and I will, I mean you’re the one with the real job and all, I just mow some yards!” I answered.

So I started wearing the panties he would put in my drawer and I was surprised how good they felt against my skin, hell even on my penis and balls! Even though the panties felt good, since they were under my clothes I didn’t mind, you know, because no one else could tell!

That summer we were invited to a BBQ and swim at his works campground. He told me how good all the food was going to be and what a great time we could have! BUT when I asked him for a swim suit, he handed me a bikini bottom and told me to wear this!

“But Terry, isn’t this a girl’s bikini bottom?” I asked.

“Yes Bob it is, actually its Mom’s old swim suit and I need you to wear just the bottoms please?” He instructed me.

“But Terry it has plastic loops on the side, I mean everyone will know I’m wearing a bikini bottom like a girl!” I whined!

“Come on Bob, let’s say that they are actually looking at your suit . . you’ve got a cock and balls, so you’ll have a lump in front and they will know for sure you a man . . right?” Terry told me!

So I put them on under my jeans and picked out a shirt to wear and told Terry I was ready! Once we arrived I couldn’t believe the number of people there, families and kids everywhere! Terry found us a spot at a picnic table, with his boss’s family! After we ate I heard others talking about going swimming. I looked at Terry and he told me sure let’s go. We arrived at the pool and because we had our suits on we could just change our clothes right by the pool and jump in. Sure enough as I was walking to the diving board I heard one mother tell another.

“Isn’t that a woman’s bikini bottom that boy is wearing, there, right there well you’ll see him when he comes back by!” She said. I swam to the end of the pool and as I was getting out I felt my suit slip off! I grabbed them as quickly as I could but not before a couple of girls saw me.

“Did you see how tiny his penis is, I mean my little brother’s dick is bigger than his!” She said laughing. As soon as we got back to the car I told Terry about the things people had said today and how embarrassed I was, you know wearing woman’s clothing in public!

“Hell Terry it didn’t even dawn on me that when I went to the Changing Room to get out of my wet suit, I would be putting my panties on in public . . God Terry didn’t you see those men laughing and pointing at me?” I asked.

“Bob, I’m sorry those men were being jerks, so they have lots of money and we don’t . . ok hell I would wear Mom’s old panties too but they are way too small for me!” He told me, almost mad!

Back home that night I began crying in bed again, so Terry woke me up and I crawled in bed with him. Before morning, I felt Terry rubbing my nipples again and I could feel his hard cock up again my butt cheeks! I was afraid he was asleep so I didn’t want to wake him . . he’s got work today! When I did get out of bed to go pee I noticed that the back of my panties were wet! I started to tell Terry but told me that since I began to cry again, I had to sleep with him each night!

That night I felt him rubbing and even pinching my nipples again and then noticed he was actually humping again my butt cheeks. So this night I stayed awake and felt him cum through his underwear and onto my panties! I wasn’t sure what to do but I finally approached Terry and told me about him rubbing my nipples!

“Like hell I am Bob, your dreaming . . you’re just being silly!” Terry said!

A couple of nights later when I felt him humping my butt cheeks as soon as he shot his cum all over himself and me, I rolled away from him and woke him!

“Terry awake up, Terry!” I yelled. “You got cum all over your underwear and on my panties too, just look!"

“Sorry Bob, I guess I was dreaming and thought you were a girl . . you know wearing panties and stuff!” He replied. “Come on Bob, hell you even have wet dreams . . admit it, I can see the white crust on the front of your panties . . I mean hell I’m only human!”

“Ok Terry . . I’m sorry I got mad. It just seemed strange to me feeling your cum on my panties! I shared.

That night as we were getting ready for bed, Terry came out of the bathroom.

“Bob I tell you what, why don’t you take your panties off at night so in case I do have a wet dream, your panties will still be good for you to wear in the morning . . ok?” So I stopped wearing my panties at night and while Terry was still humping against my butt cheeks now and then, at least he didn't get cum on my panties!

One night I was awaken feeling Terry’s cock, I mean his bare cock pushing against my butt cheeks! It felt kind of wet and then I felt it pushed against my asshole. God I was scared, I mean what in the world was happening? Then I felt Terry drape his arm over me and begin rubbing my nipples!

“Oh sweetheart I love you,” Terry whispered like he was asleep. “Let me make love to you honey.” And with that I felt his cock head push into my asshole! Oh shit, what is he doing, is he going . . too late I felt his cock push fully into to me and even felt his balls up against my butt cheeks! Once he was in he didn’t really fuck me in and out, it was more me feeling his cock throbbing and then BANG I felt his cum shouting inside of me! Next I heard Terry begin to snore and snore loudly but his cock was still inside of me! He finally became soft and it pulled out but the sheets were wet and so was my asshole! I got up and went into the bathroom gabbed a bunch of toilet paper and wiped my butt cheeks!

The next morning I waited for Terry to say something but it was our regular morning, him making our breakfast and then leaving for work! All day I wondered about what had happened but couldn’t figure out how to tell Terry or what to say to him.

Several nights went by without Terry fucking me again until I felt something against my mouth. I opened my eyes only to see Terry’s cock against my mouth. He started to push more and I felt the tips push between my lips! That was it I had to wake Terry!”

“Ter . . .” I got nothing else out because the second I opened my mouth his cock pushed in deeper and then he started pumping in and out! I guess it was lucky for me that he wasn’t pushing too much that his cock went into my throat! Just like him fucking my asshole, Terry pumped until his cum loaded up my mouth! And just like before some of it ran out onto the sheets.

I had to tell Terry what he was doing but lately he has been so nice to me, better meals to eat and he has even begun to buy soda pop for me to drink!

In a couple of night, he pulled me against him and pushed his cock into my asshole again! But this time he was reaching around and rubbing my penis between his fingers! That did feel good and in fact I had now become accustomed to his cock in my asshole and it actually wasn’t hurting anymore! But then I heard him.

“Bobby, I love you please love me too!” He moaned. Why was he telling me he loved me, I knew that so what did that have to do with him fucking me! He really filled me with cum tonight and what a mess! I just knew he would see the messy sheets and say something to me. I also thought it was interesting that as I started seeing new tops in my drawer, I never heard a word out of Terry about them being pretty or anything, I mean hell even they had little flowers on them and everything!