My interest began about three years ago. I was 14 then and my best friend David was same. I have always found his sister to be very attractive and when she was 16 I was not able to keep by eyes off her. She is tall, slender, with nice breasts and big pouty lips. I was in David's house often so I always saw his sister. One day I was using the bathroom and I saw the hamper was open. I looked inside and a pair of her cotton panties was on top. My dick got hard immediately as I picked them up. I just had to jerk off, so I did into her panties and then put them back into the hamper. After doing this for many weeks, I knew she had been wearing the panties that I came in. After about a year, so she was now 17 and I was 15, her bras and panties got much sexier. She had string bikini panties that were satin and really sexy. Her bras were satin and lace and made me so hard. I wanted to see her in her lingerie so badly. Over the summer she went to camp and me and Dave stayed home. I spent a lot of time and nights at Dave's house. One night I woke up in the middle of the night and I was real horny. I looked at Dave to make sure he was a sleep and he was. I then got up and slowly walked over to his sister's room. I wanted to see what lingerie and clothes she left at home. I went in and opened a drawer and it just had some socks, so I open the drawer next to it and it was almost empty but has some very sexy bras and panties. I got hard instantly. I took a pair of bra and panties and put them I her bed and wanted to see what other sexy stuff I could find. After looking through all her drawers and closets I found some nice stuff. I took a really short black mini skirt, a tight button down satin shirt and a smooth sexy pair of black thigh highs. I then quickly begin to jerk off but before I could finish I heard walking in her parents room so I picked up her clothes and ran back into Dave's room and hid the clothes in my bag. The next day when I was back home and had all these sexy clothes with, I decided to try something that I had never done or thought of doing. As I was about to jerk off with her clothes I decided to try them on. I dressed myself up and I felt so sexy. I knew my sister had wigs cause she was in the play so I put one on that was similar to Jess' (Dave's sister) hair. My dick was rock hard. As I was rubbing my "pussy" and "breasts" I did not hear my sister come into the house. She was coming home from cheerleading practice. As I was rubbing myself and fantasizing about Jess, my sister open my door and saw me. I froze in place and she was about to scream but then started to laugh and smile. I tried to cover myself but she said no. She knew they were not my moms or hers so she asked where I got them. I told her the whole story and that it was my first time. She then laid down next to me still with a big smile on her face and she began to rub my tits. I was thought she was just joking around with me but she then laid on top of me and put my hands on her ass. She was only wearing her uniform with a very short skirt and thong panties so I got her whole ass in my hands. I decided to give in and started to kiss her and feel her whole body. She and I for that matter were having so much fun. She said it was like doing it with another girl until she got to my hard cock. She began to suck me when she said to fuck me in her ass. I wasn't sure if I should but she kept on saying it so I went behind her and lifted up the back of her skirt and pulled off her panties. She had such a nice ass. I then took my dick and slowly put it in her. I was pumping slowly at first, but she said fuck me harder. I keep on doing it and she kept on screaming fuck me fuck me harder. I finally let my load go in her ass and pulled my dick out. As she was walking out of my room she said lets do this more often and wear my clothes whenever you want I find u so sexy in them. I did not feel bad after fucking my sister and just imagined doing it again while wearing her clothes. The next day I was looking at my sister's clothes and she had such sexy stuff. I put on her thong satin panties and her cheerleading uniform and also tried on one of her teddies. I then put my clothes back on and went down stairs. In about five minutes my sister came home and said I want to have a lot of fun right now. She said she wanted to be the "guy" and me the "girl". She brought me up to her room and to me to get naked. I did and then she started to take out some clothes and dress me. She pulled a pair of black lace thong panties around my waist. She put a black lace bra around me and used socks to give me nice breasts. She pulled a pair of thighs highs on me and connected them up to a garter belt. She them put a really sexy and really tight see through blue top which covered a white tank top. She then put a really short sexy skirt around my waist. She the sat me down in front of her mirror and took out make-up. I decided to let her do it because why stop now. After putting on the make-up and wig you could not tell I was a guy. She then went into her closet and came out wearing jeans and a polo shirt. She also tied her hair back and put a hat on. I noticed a slight bulge in her pants and was very curious why it was there. She then began to kiss me and feel my chest. She lifted the shirt and began to lick my tits. I then knew I was playing the female role so I started to unzip her jeans and slipped my hand in. I found out what the bulge was, it was a huge strap-on dildo. I got real nervous for a second but if she is pretending to do it with a women I may as well do it with a guy. I started to play with it and then pulled it out and pulled her pants down. We then moved into a 69 and I sucked her dick as she licked my pussy. She the got up and turned me over lifting my skirt up and moving the panties away. She said she would do it slowly as she inserted the dildo into my ass. She pumped away at my ass getting faster and faster. I started to moan like a girl. We knew our parents were coming home soon so we stopped and took a shower together, lathering each other with soap. We both knew we were having so much fun doing this and we keep on doing this for a long time. The summer was coming to a close and Jess was coming home so I was excited that I could stare at her again. She had been back for about a week and I was sleeping over again and I was really horny this time and wanted to fuck her and suck on her tits that have developed so well. I wanted her to catch me wearing a pair of her panties and bra. Dave was in his parent's room showering so I knew he would not see anything. I went into the other bathroom very quietly so she would not hear me and put her lingerie on. I was playing with myself on the floor when she walked in and said so I finally caught you. Before we I could say anything she said she knew it was me cumming in her panties because she saw the panties right after I was in the bathroom and checked every time I was in there house. She was happy and walked over to me and said I will wake you up at 2:30 in the morning so we can have some fun and she gave me a quick kiss and my hard cock a quick squeeze. That night I could not sleep and was up when she walked into Dave's room. I got up and we went down into to their basement where they have a guest bed, so no one would hear us. She brought some clothes with her and told me to put them on. We then began to kiss and I started to feel her big firm breasts. She had such nice nipples I just had to suck them so I lifted off her shirt and sucked on them hard. She saw my cock getting hard so she took the panties off to relive me. She started to jerk it off and then gave it a quick lick to moisten it before she opened her pussy up for me. I pushed her knees up and out and slowly slipped my dick into her tight pussy. We then finished and went to sleep. The next day when I was home, I found something interesting in my bag. Jess had put some of her lingerie in my bag and a note which said please cum on my lingerie and I want to fuck you again. As I was putting the lingerie away so my parents would not see it my sister came into the room and said you took more lingerie from Jess when you have all of mine. I told her that she had put these in my bag. She hen asked how she found out that I liked lingerie. I told her how I purposely got caught by her in the bathroom and then showed her the note that was in the bag. My sister I was a very lucky boy to get to fuck two girls. She then said would you like to fuck us both at once. I responded with a yes, but then I said how do you know she would want to. She said she is good with other girls and will fuck her and then asked about a threesome and she will definitely say yes. My sister said that she would leave a note tomorrow from me to come to my house at 3pm. When she arrived I was making sure she would not see me and my sister answered the door in her bathrobe to make it seem like she just got out of the shower. She kept the robe loosely tied so Jess would be able to see her perfect breasts. Jess asked if I was home and my sister said no but said I would be home in 10 minutes. She brought Jess into the house and sat down with her to talk. They started to talk about me and Jess told everything that we did together. My sister said that story made her very horny. She began to rub her pussy and tits and moved closer to Jess. Jess began to unbutton her shirt revealing the sexy lingerie she had on. My sister then moved over and began to kiss Jess. I got so hard watching this from the other room. They continued to kiss and after playing with each other's tits they got into a 69 and were moaning like crazy. Before either reached an orgasm my sister took out a double dildo and they both placed it in their ass and started to fuck each other. They both finally reached their orgasms and put their clothes back on. Then my sister said how we had also fucked and would love to have a threesome with you. She said she would love to and then my sister told me to come into the room and I did. As I sat down with my hard on, my sister took her hand and started to jerk me off. As Jess was about to join in she asked if we want to have even more fun. We both asked what she wanted to do. She said that me and my brother have also fucked. We have done the same things as you, so I am sure he would not mind that another guy was here. We both agreed and his sister called their house and told what we were doing and he said, I would be real glad to do it. While we were waiting for Dave to come I put on some sexy lingerie and clothes, and Jess and my sister put some of my clothes on. As soon as Dave arrived his sister handed him some lingerie and told him to put it on. Now that me and Dave were the girls and our sisters the boys we decided to have some fun. We first started to kiss and feel and our sisters felt us. Then Jess had an idea. She said that as boys you like watching girls go at it with dildos on so why don't you and Dave have some lesbian sex. So I went over to Dave and began to kiss him after deep tongue kissing I started to feel and suck on his tits. And he rubbed my pussy. Then I flipped Dave over and before he could say anything I stuck my "dildo" right into his ass. I keep on pumping him real hard and he was moaning like a girl. After I finally shot my load in his ass day said let me fuck you, so I turned over and stuck my ass in the air. While he was pumping my ass my sister got her head under me and started to suck on my cock. Then Jess got involved by putting my sister's dildo in her ass. We had one big orgy going. We were all moaning and pumping away at each other. WE all had our orgasms at the same time and said how we would love to do this many many more times.
Boy Brides Ch. 6May 7, 2002
Darren, his bride, & her sister have sex in window.
Sex: 101Nov 16, 2002
He stays home from school to learn the fine arts of sex from Mom.
Sex to a T Ch. 1May 8, 2001
Couple gets hot & steamy on the subway.
Sister BeautifulJul 26, 2002
A beautiful Indian family affair.
NeighborsFeb 1, 2009
An older man's fantasy come true.