I’ve been mulling this over in my head for quite some time now as to whether I should put down some very erotic memories into a permanent form and to share these events with a global audience. I did decide, obviously, to finally share these stories. These stories will be broken into parts. The overall story is of how a bet I made with a female friend turned into a lifelong obsession with having sex with women who were sisters. I have been lucky enough to have had 3 sets over the last 20 years, but I am always on the lookout for a 4th.
Part 1 - How it all started
When I was 17 a close friend, Andrea, and I decided to make a bet. She was a very sexual person and knew how badly I wanted to have sex with her. She decided to give me an impossible bet where if I could have sex with two girls that were sisters she would “give me the kind of fucking you don’t walk away from”. I’ll never forget those words. Now what was so special about Andrea? Well, I had known her since we were both 8 years old. I had watched her grow up and she was my closest friend. When we were both 11 she started to ask me about my body as she had started to notice boys. We started playing games with each other starting then. At 14 she asked if she could do to me what she had seen her older sister do to her boyfriend. Not really knowing what she was talking about I said “sure”. It was then that I got my first taste of a blow job. In all honesty, it was not good at all really, she she just put my dick in her mouth and moved up and down. She didn’t close her mouth around it at all. That was the only sexual experience I had with her.
As we got older she started dating and like most teenage girls, had many boyfriends. When we were 17, just before the bet, I was staying at her house for the weekend to help her family move to a new home. One night she and I were at the new house while her parents went out to dinner. Andrea asked that I “go for a walk” so she could have a quickie with her new boy toy. I demanded payment as it was pretty cold outside. What I got made the 30 minutes in the cold worth it. She gave me a sensual striptease down to nothing and then gave me a lap dance. This girl had an amazing body. At 5’ 4” she weighed just under 100 lbs. Her ass was smooth and her pussy looked so inviting. Her tits were a solid C and had the cutest nipples I have ever seen...even to this day. That striptease is seared into my memory, especially when she faced away from me with just her panties on, bent over at the waist and took off her last stitch of clothing. The view of that pussy will never leave me. It was after my duty outside was done that we made the pact. I prayed that I could make this happen.
I had been having a relationship with my girlfriend Brenda at the time for about six months and I knew at that time that her older sister, Cindy, was interested in me. I decided to go for broke as my constant blue balls from thinking about Andrea were getting a bit out of hand. Cindy was home from college for the holidays and she and I were pretty friendly with each other. Brenda and my relationship had cooled some and Cindy knew it. I came over to their house one day when I knew Brenda was at work to talk with Cindy.
Cindy was wearing loose fitting sweat pants and a t-shirt with “UOP” written across the breast when she answered. She invited me in as soon as she saw me. We chatted a bit about unimportant things and her mother walked by on her way to the store. It was then that I decided to tell Cindy that Brenda and I were pretty much over as we really did not have much in common. Cindy said she was sorry to hear that, but had the feeling that there was more to my visit and more to the reason why I had lost interest in her sister. I thought hard about how I was going to ask Cindy to have sex with me, but ultimately decided to tell her about Andrea and the bet. Honesty is the best policy, right? The look on Cindy’s face after I was finished talking made a chill go up my spine. It was a mixture if interest and disgust. I asked her to not tell Brenda until at least after I broke up with her later that day. Cindy promised she wouldn’t tell Brenda what I had told her, but when it came to having sex with her I should not hold my breath.
Knowing that Cindy was a lost cause. I started to think that I could tell Andrea that I slept with Cindy and Andrea would never know I lied until after the deed was done. That thought was dashed when I talked to Andrea and she said she wanted proof. She already knew about Brenda, but wanted a picture or Cindy could tell her in person that it was done. Later that night I broke up with Brenda and went back home. As I laid in bed, I figured that I would never get the chance to fuck Andrea.
The next day started normal. I went to my part time job after school. After closing the store I started walking home when I saw Cindy in the parking lot leaning against her car. I looked around to see if Brenda was there to hit me with a steel pipe or something, but thankfully she was not. Cindy asked if I wanted a ride home, she wanted to talk with me about Brenda. I only lived about a mile away from where I worked, but that car ride took a lot longer. We talked about why I broke up with Brenda, Andrea and the bet. It was then that Cindy’s hand came to rest on my crotch. She stopped at a light and looked right at me and said “I would never fuck my sister’s boyfriend. But I guess you are not her boyfriend any more.” My dick jumped to attention. Cindy then told me that she would help me out if I would wait for 7 days. Cindy said that she wanted this to be worth her while, so she wanted me to promise to not masturbate or have any sex for 7 days.
I have heard about long weeks, but this had to be the longest of my life. Cindy called me and told me to come to her parent’s house that Saturday. She promised me that she would be the only one home and we would have several hours to “get things done”. That Saturday I cleaned myself up and drove to Cindy’s house. Cindy answered my knock at the door wearing just a long t-shirt. She looked stunning and invited me in. True to her word, no one else was home. She directed me to sit in a recliner in the living room and she sat across from me. We talked a bit and then Cindy asked me if I had brought protection. I had brought enough condoms for a month of constant sex, so I told her yes. She said “Good” and leaned back in her chair and let her legs part.
I could see that she was not wearing any underwear and she was neatly shaved. I had never really seen a shaved pussy in person, so I found my self staring. Cindy said “I’m glad you like what you see. Come over here.” while directing me over with a sensual finger. I walked over to Cindy and she told me to kneel down. She then directed my head between her legs and I began to lick her pussy. I was soon aware that she was as excited about this as I was. Her pussy was very juicy and the heat coming from her was intense. I have always loved eating pussy, so I took a good long time on Cindy’s. I had never brought a girl to orgasm with my mouth before, but Cindy’s was so intense I thought she was going to crush my head. Cindy then pushed my head away and stood up. She then took her shirt off and exposed her nice, perky tits. She told me to stand up. I decided that I wanted some more control and leaned in to lick her pussy some more. She collapsed back down into the chair for 2 more orgasms. Cindy was quivering and breathing heavy now. She lifted her head and said “DAMN! Why did Brenda let you go?”
I stood up and started to undress. I told Cindy to just sit back and relax, I’ll take good care of her. Saving my underwear for last I took off my clothes. I pulled down my boxers and my erect dick popped out. I walked close to Cindy and asked if she wanted to suck on it. She reached out and hungrily started sucking on my throbbing member. Cindy’s lips and tongue worked in perfect concert. I had to have her stop not long after starting because I did not want to blow my load too early. Cindy asked what was wrong and I told her I didn’t want to cum to soon. “You had better start fucking me then” came out of Cindy’s mouth and I leapt between her legs, pushed my dick into her and started long, slow strokes. It was then I realized I hadn’t put on a condom. I stopped again and started to pull out when Cindy pulled me back in with her legs. Once again she asked what was wrong and I told her about the condom. She said she didn’t care and that she didn’t want me to stop. I kept shoving my dick into Cindy’s juicy pussy over and over. I started to feel the pressure build as I approached climax. I stepped up my speed and then started to pull out again when Cindy again pulled me back in and yelled “Don’t you fucking stop! Cum in me!” I shot my load deep into Cindy’s tight pussy when I felt her have another orgasm. Her pussy milked my dick dry as we both panted heavily.
I pulled my dick out of Cindy and laid back on the floor, spent. Cindy stood up and laid down next to me with her head on my chest. “You really did wait a week, didn’t you?” she said. I told he that I had. Cindy’s head then moved back down to my dick and began to lick and lightly suck the head. I had never had a girl suck on me after I came before so this was a new, exciting experience. With Cindy’s help my dick was soon hard again and she was taking it all into her mouth. After a while, she stopped sucking on me and stood over me. “Do you want to fuck me again or should I just blow you off?” she asked with a smile. “Fuck...definitely fuck. Cumming in you was amazing and I want to do that again.” I responded. Cindy then crouched down and put my dick back into her sticky pussy. She rode me softly with her pussy wrapped tightly around my rod. Within a short time I felt that same pressure and came again in her wet snatch. Cindy did not stop fucking me until my dick was soft again.
After the second round I realized that we had been going for over an hour and a half. I asked if I should get going as I did not want Brenda to find me there. Cindy told me to not worry as everyone was gone until later that evening. We walked back to the shower and cleaned each other and we both did a bit more oral as a way of playing. We sat naked back in the living room and I asked her if she would tell Andrea about what we had done. Cindy asked me why. I told her that I had to have proof of the encounter with ether the girl talking to Andrea or I had to have a picture. Cindy jumped up, left the room and came back with Brenda’s Polaroid camera. Cindy handed me the camera and went back between my legs and started sucking my dick again. Once it was hard I had her pose and took the picture.
Cindy and I then got dressed and said our good byes. I told Cindy that it was the best sex I ever have had. She then told me that it would not likely happen again and that this was a one time deal. I told Cindy I understood, but was still upset by the news. Cindy was a much better fuck than I had imagined so it made my excitement for the eventual sex with Andrea all the more intense.