I enjoy putting on women’s clothes. I am in my fifties and have been doing it since I was 10 years old. I have 7 sisters and I am the only boy. I am right in the middle of all of my sisters. There aren’t 4 years between the oldest and 4 years to the youngest. The first time I got caught I was 12 years old. This is my storyI would go upstairs into my sister’s room which at the time was also my room. There were only 3 bedrooms upstairs with 8 kids to sleep in. There was always an empty side of the bed for me. I didn’t really have a room to myself or a single bed to myself. I would randomly pick one of my sister’s beds to sleep in every night. It depended on how I felt and who I wanted to sleep with.I would find some silk panties, a bra from one of my older sisters, and a cute little sundress that I really liked to wear. I found some nylons from my mom’s room and had them hidden upstairs in the bathroom. I would get undressed and put the silk panties on and they would feel so great against my skin. It would start to get my cock so hard and I would rub it through the underwear. It felt so good. I would then put on the bra and stuff it with some of my socks. I would then put on the nylons and that would almost bring me over the edge and cum directly into the silk panties. I would have to stand straight and not move for a couple of minutes then my hard on would subside a little bit. I then would put on the sundress and smooth it out and start to twirl so the bottom part of the dress would puff out. I would get that feeling again in my cock and I’d have to stop and stand very still. I would do this for a long time until I came into the silk panties. Well, this time I was at the part where I had to stand real still otherwise I would come to quick. I heard my older sister at the foot of the stairs hollering for me. I hollered back that I was upstairs and I would be down in a few minutes. I heard her coming up the stairs. I panicked; my heart was beating so fast, with the combination of almost having to cum and the thought of getting caught with girls’ clothes on by my older sister. My older sister is so hot; she is 5’5” with long flowing brunette hair and huge breasts that I have seen several times peeping at her through the bathroom door. She also likes to show them off wearing a tight halter top that barely covers the nipples. I went into the bathroom and hid in the closet, hoping that she would just not find me and go back downstairs. I was in there so long that my cock was on the verge of Cumming again and I couldn’t hold it back much longer. All of a sudden the door opened up and there stood my sister wearing very short shorts and her pubic hairs were popping out on both sides. I nearly fainted when I looked up to see her with a short shirt that barely covered her breasts. When I looked up my eyes followed upwards from the camel toe with pubic hair sticking out to her belly button all shiny and aglow. I could make out small white hairs all the way up to the bottom of her breasts. Looking up I could see the outline of each breast with the nipples conveniently hidden under the shirt. Then I made it up to her face and I was shocked to see her smiling.She said, “Bobby what are you doing wearing your sisters clothes?” I said, “Kelly, I like to do it and have been doing it for a couple of years.” She said, “Come out of there and let me take a look at you.” Every time I moved around my cock was getting hard again and was pushing out on the sundress. She helped me into the bedroom and said, “Twirl for me”. I didn’t know what to do so I started to twirl and when I stopped she just looked at me with what I thought was hunger in her eyes. She was looking down at my crotch and I was thinking wow my sister is hot. She said, “What is that” pointing to my huge erection pushing out on the dress. I lifted the dress up and she said, my lord Bobby, your cock is huge and must be hurting straining like it is on those silk underpants.” I said, “Yes it is seeing you in those skimpy shorts and short shirt. I want to touch you in ways a brother shouldn’t but would you let me?” She didn’t say anything just reached down and grabbed the bottom of the sundress and lifted it up off of my head. She then put her hands into my silk panties and slowly took them off of me. She put her hands onto my aching cock and slowly started to jack me off. I was leaning back and enjoying the massage on my cock. I then felt her put her lips on my cock and I nearly came right then and there. It took great constraint but I stopped myself. I was in seventh heaven and when she stopped and stood up I couldn’t believe my eyes when she took off her top and her huge tits with small areoles were thrust into my face. I was kissing them all over and caressing each nipple with my fingers. I took the left one into my mouth and started sucking on it. The nipple got real hard and stuck out about a half inch. Kelly still had her hands on my cock and was stroking it faster and faster. I started to moan and she said, “Bobby I need you inside of me.” She lay down on the bed and I slowly climbed on top of her and my cock found its way to the opening. I slowly pushed and she said “Oh Bobby, I have waited for this moment since I first noticed you checking me out in the bathroom. I said “Kelly, you have the biggest bush on a woman that I have ever seen.” She said, “Oh, Bobby quit talking and push it in. I want it so bad. Fuck me Bobby, fuck me.” I pushed it in and it felt so tight and hot. I couldn’t believe I was fucking my sister and she was enjoying it. She had her legs wrapped around my ass and was pumping me for everything I had. I said, “Kelly, I am going to come inside of you.” And she said “Bobby, give it to me, give it to me” and I came like I have never came before. She was arching her back to the point that her belly was extended into my chest and I came so violently that I felt the come coming out onto my legs. It was the greatest sex I had ever had and she was so lovely lying below me. We lay there for a few minutes when I heard giggles from behind me. I looked back to see three of my other sisters, Peggy (11), Jenny (13) and JoJo (15) standing there taking their clothes off. I said “what are you guys doing taking your clothes off for?”. JoJo said, “We are next little brother, and we won’t be so nice.” I spent the next four hours fucking each of my other sisters and they were great.First Jojo said, “Robbie I want you to take Peggy and fuck her so hard that she never wants to fuck again.” I asked Peggy if I could take her panties off and she said, “Robbie, I want you so bad that I would slowly strip so you your hard cock would grow to epic portions. The bad thing is that your cock is so wonderful that I would suck every inch to see where you’re cum comes from.” I said, “Peggy your lips are so lovely that I want you to suck me till I come.” “I want your sisters Jenny and JoJo to latch onto me as well while you suck and all three of you can suck on my cock and make me explode onto your faces. I would love to come onto all three of your faces at the same time. Oh I love all that you do and I am coming on your faces at the same time!!! Oh, Oh, Oh, ugh, ugh, ugh, I am coming……. Oh Peggy I love the fact that you three loved my cum and that you sucked me off.”Peggy said, “Robbie, do you like to wear women’s panties, and do you like to wear women’s dresses? I thought that you had a dress on when I came upstairs? I liked the dress you had on! The yellow sundress you had on was so beautiful that I loved it. You must wear more dresses so we can see more of your feminine side. We just loved the way you looked in a dress and just wanted to see you again in a dress and wouldn’t wait to see you in the beautiful sundress.
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