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 and this is the 2nd installment. 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.
I slowly closed the door at Cindy’s house and walked back to my dad’s car, exhausted. I had a great time with Cindy, but my thoughts were focused on Andrea. I held a small square photograph in my hand that was my ticket into Andrea’s pants. I fought the urge to drive over to Andrea’s house with the picture as I knew I would be too tired to really enjoy the experience. I had waited this long, I could wait a little longer.
I called Andrea up the next morning and asked her to meet me by the drama room before school as I had something very important to tell her. She asked me if everything was alright and without missing a beat I responded that everything was just fantastic. A short time later I found Andrea sitting on the bench by the drama room, waiting for me. I sat down next to Andrea and took a long breath. Now is not the time to be nervous and wuss out I told myself. I looked over to Andrea and was able to mutter “I did it”. “Did what?” she asked. I slowly reached into my pocket and pulled the picture of Cindy with my dick in her mouth and showed it to Andrea.
Andrea sat there for what seemed like an eternity just looking at the photograph. I could see her shoulders shake a little bit as she finally looked back at me. “I can’t believe that you actually did it.” she whispered. I suddenly realized that she was extremely nervous as well at that moment. “What will Brenda say when she finds out you fucked her sister?” Andrea asked with a look that stuck me like lightning. “I broke up with Brenda 2 nights ago. Things just were not working out between us.” I told her. Andrea then took a deep breath and said “I know I promised you, but I never thought you would actually do it. I have a boyfriend...it just wouldn’t be right.”. I was stuck into silence by her words. Andrea had never had a boy friend that she cared for enough that she wouldn’t cheat on, so I knew she must have cared for this one. I knew what I wanted, but I wanted Andrea to not have to regret something either. I valued our friendship more than that.
I told Andrea “Its ok. I understand. I don’t want you to do anything you wouldn’t want to do. Our bet will just have to remain a ‘Gentleman’s Bet’”. Andrea was almost crying when she uttered, “I don’t want this to ruin our friendship. I want you to know that I would honor our bet but...”. “You don’t have to honor it.” I said, “I will always be your friend.” Andrea gave me a big hug and cried on my shoulder and said “Thank you”.
Life continued as normal for the next several months. We were getting ready to graduate and Andrea was accepted into Stanford while I had decided to join the US Navy. Prom was just around the corner and I was going stag while Andrea was going with her boy friend. Three nights before the prom I got a call from a hysterical Andrea. “He dumped me, that fucker dumped me!” she cried. “Calm down, please calm down. What happened?” I asked. “That asshole Steve dumped me! He said that he found someone new. Some fucking cheerleader!” she replied. I asked if she wanted me to come over and she said “Yes” between whimpers.
I pulled up at Andrea’s house and there was Steve on the front porch yelling at Andrea. Steve was calling Andrea all sorts of names from “Slut” to “Whore”. As I approached Andrea saw me and Steve saw her look and turned around. “Oh, look. Its your best buddy! What the fuck are you doing here?” he asked. “Better question is why are you here? You broke up with her. Leave her alone.” I replied. Steve then started to get in my face and well, I just don’t like that. The next thing Steve knew was that he was on the ground. This guy had a glass jaw if I ever saw one. I told him to get lost and to not bother Andrea again. After a few more choice words Steve left, never to return to Andrea’s life.
I spent the next 3 hours taking with Andrea and helping her calm down. She had really loved Steve and was heart broken. I kept telling her that things would be ok and that she could and would do better. By the time I left I was able to pull a few laughs and a smile from Andrea. The next day at school Andrea approached me and asked “Do you have a date for Prom?”. I told her I was a stag and she asked if I would like to join her. I answered with an enthusiastic “Yes”. Andrea gave me a big hug, whispered in my ear “I guess I don’t have that little problem anymore. You had better be ready.” and quickly walked away. I was left in shock with a raging hard on that nearly split my pants. “Holy shit, is this actually going to happen?” I asked myself. 2 days to Prom, this is gonna be awesome.
Andrea made herself scarce over the next two days until I picked her up for the dance. She looked amazing in her formal, strapless blue dress that went down to her ankles. There was a slit on one side that rose to halfway up her thigh that gave me tantalizing glimpses of her smooth, well toned legs. Her hair was down in flowing curls around her shoulders that seemed to dance with her every movement. I found I couldn’t speak when I first saw her, but I did soon recover. “You look absolutely stunning!” I told her. “I hope you two have fun tonight!” her father said. “Just remember to be home by eleven.” “Eleven? What the hell? The dance ends at eleven.” I thought. How are we supposed to consummate our bet with that timeline? “Ok dad!” Andrea replied as we walked to my dad’s car.
We drove in silence to the Prom that was being held at a local Civic Center. I decided that we could wait on our bet and I would show Andrea the time of her life. We chatted with friends and danced until our feet hurt that night. I looked at my watch and saw it was almost 10:30. “I guess I have to get you home.” I told Andrea. “What? Why?” she asked. I reminded her that her dad wanted her home by eleven. Andrea then laughed out loud and called one of her friends over and asked her “What am I doing tonight?”. “Staying at my house with my parents until you have to join your mom and dad for pictures at eleven.” Andrea then looked over at me and gave me a mischievous smile that aroused me almost instantly. “I told you I had it covered.” she said and placed her hand on my growing bulge. “You had better not disappoint me. We have all night.” she said as she walked away with her friends, leaving me alone with my pornographic thoughts.
The dance ended and everyone started to filter out to various after parties. Andrea said goodnight to her friends and we walked out to the car together. I walked to the passenger side to open the door from her, but stopped and faced her. “Are you sure you want to do this?” I asked. Her answer was a simple smile and a deep kiss. We drove to a local hotel that was across town where I had rented a room. We walked into the room and I closed the door. I looked over my best friend again and remembered all of the times I have dreamed about her and wished I could have her and now it was about to come true.
Andrea walked up to me and said quietly “You look tense. Lets get you out of that suit.” She slowly took my jacket off and then my shirt. She lead me to the bed and sat me down and walked a few steps away. “Do you remember how I paid you off when I wanted some time with Steve?” she asked with a grin. “Hell yeah I do!” screamed through my head but I only managed a soft “Yes I do. Best night of my life.” Andrea looked me square in the eyes and said, “Really? Even after fucking Brenda and her sister?”. “They were just a road to the real prize. A means to an end.” I replied. “Well. Now that you have reached your destination, what do you want to do?” she asked while slowly unzipping the back of her dress. As I watched the silky blue dress fall gracefully to the floor, I muttered “Give you a night you will never forget.”
Our eyes met and there was a fire raging there that I had never seen before. Andrea walked over to me, took my hand and lead me to a chair. She pushed me down to sit in the chair with a soft hand on my chest. Wearing only a bra and panties, she began to dance around me, gently tracing a line along my neck and shoulders with a single finger. “Which one do you want me to take off first?” she asked while standing behind me. “The panties” I replied. The next thing I knew, a frilly, white pair of panties fell in front of my face and landed in my lap. My heart quickened it’s pace and her finger again touched me and she started to walk back around in front of me. Andrea stopped directly in front of me, allowing me to gaze at her crotch. She had shaved all of the hair away and the milky smooth skin begged to be kissed. I could see the evidence of wetness glistening on her pussy’s lips.
Andrea started another circuit around me, still teasing with the slight touch of her finger. She stopped behind me again and her white, lace bra fell into my lap. There was the finger again, gently tracing it’s way back in front me me. Andrea stopped in front of me, just out of reach. My eyes moved from her wet pussy up to her beautiful, perky breasts and then to her face. She was smiling. Smiling like she was glad that I enjoyed what I had seen. “What now?” I croaked. “You wait until I am done. You still want that lap dance don’t you?” she replied. I simply nodded in reply.
“Hands down, no touching me.” Andrea curtly ordered, “If you touch me, then I will stop.” Andrea was really enjoying this I thought. She sauntered over and began to dance. Spinning around, bending over and giving me amazing views of her body. She then took one leg and placed it across me, putting her foot on the chair. She then brought her crotch into contact with my pants that were near bursting from my throbbing member underneath. Andrea ground her pussy onto my bulge until I couldn’t take it anymore. “Please, let me touch you.” I stammered. “You may on one condition.” she replied, “I want you to eat me out like you told me you did with Cindy. I want to feel what she felt.”.
I scooped Andrea’s naked body up and placed her on the bed. I spread her legs with my hands and started kissing her feet and slowly worked my way up her leg. As I neared her waiting pussy, I could feel her trembling with anticipation. I started to slowly lick her clit, putting subtle pressure with my tongue. Her pussy was very wet and I could tell that she was really enjoying what I was doing. Andrea’s back arched in orgasm as I continued licking and sucking her cunt.
I paused to let her catch her breath and she looked into my eyes with a hunger like no other. “It’s your turn now.” I told her. Andrea stood up and began to take off the rest of my clothes, leaving my boxers for last. “I have a surprise for you down there.” I told her as she grabbed my underwear. She slid my boxers down and saw that I had also shaven myself. “Oh, wow!” she exclaimed and licked one of my balls, “I have never had a guy shave for me before.” Her tongue then slid from my balls, up the shaft and she then took my dick into her mouth.
I had dreamed of this moment so many times over the years, imagining the feeling of having her suck on me. Years of pent up sexual energy soon, and unexpectedly came flowing out of me as I ejaculated deep into Andrea’s mouth. To my surprise, she did not stop, drank it down and kept sucking. Andrea sucked every drop of cum out of my dick and continued to suck and play with it and in no time at all I was hard as a rock again. Once my member was up to the task Andrea said “Ok, my turn.” and started to lay her leg across me. I stopped her and said “No, I want to fuck you.”. “Oh you do, huh? You going to cum in me like you did Cindy? You think that because she and I are on the pill you can just cum in us all you want?”. I grabbed Andrea and pushed her onto the bed face down. “I’ll fuck you however I want.” I said “I am going to make sure that you enjoy every second of this.”
With Andrea laying face down on the bed, she raised her ass up so I could gain access to her juicy pussy. I sat there, between her legs for a few moments. Looking at my dick, so close to her pussy, I was about to get what I had wished for. Andrea, saw me hesitate, rolled onto her back and spread her legs. “What are you waiting for?” she asked, “I want you inside me.”. With that helpful statement I placed my dick at her opening and slowly slid into her. Andrea’s pussy was hot, wet and tight. The pleasure grew with each inch I slid into her. I could tell that she liked it too as her eyes rolled back, her back arched and her toes pointed. Once I was all the way in I started a slow, gentle rhythm. I watched my dick go in and out of her pussy, each time getting more and more wet as her juices flowed.
After several minutes I pulled out and said “Let’s do some doggie. I want to see your gorgeous ass while I fuck you.”. With a smile she obliged. I started to fuck her again and saw her pussy wrapped tightly around my cock. I continued the slow rhythm for a time and then asked “Are you ready?”. “You bet I am!” she replied. I picked up the pace and before long I was slamming my dick deep into her pussy. Andrea started to scream “Oh God! Yes! Fuck me!” and my balls slapped against her on each thrust. I began to sense the familiar pressure growing in my balls. “I’m cumming!” I exclaimed and Andrea pulled herself off my dick and took me deep into her mouth. I came hard into Andrea’s throat and she once again swallowed all I gave her.
I fell onto the bed, exhausted. Andrea sat on her knees next to me. “You are amazing.” I told her with a smile. “You are not so bad yourself.” she replied with a grin, “You don’t know how long I have wanted to do that.” It was then I realized that she had been interested in me as well. “Why didn’t you say something sooner?” I asked. “You or I were always going out with someone. I didn’t want to ruin a chance you or I had for a relationship.”. “What about us?” I asked, “Why couldn’t we have a relationship?”. “You know that wouldn’t work out.” she replied. “We are great friends, but I don’t see us having kids together or getting married. What we have is vastly different.”
I could see where Andrea was coming from. In all of my dreams and fantasies about Andrea I had never thought beyond the sex. She had also come to this realization as well. “As long as I can be your closest friend, I will be happy.” I replied. “Maybe we can be friends with benefits from now on?”. Andrea looked at me and started to laugh. “I guess so. At least I know you are not a total freak.”. “And I know that you are not a possessive bitch.” I joked. The fire came back to her eyes and she glared at me. “Do you remember what I said when we made this bet?” she asked. “You said you would give me a fucking I wouldn’t walk away from.” I replied. “Looks like you can still walk. I guess I need to keep going!” she said as she took my dick into her mouth again.
This time I let her do what she wanted. She got me hard again and straddled on top of me. My dick slid into her pussy as she rode me up and down. “Warn me before you cum.” Andrea said between moans. “Will do.” I replied. She continued to ride me, hitting me harder with each thrust. Andrea was fucking me harder than I had ever been fucked before and she was loving it. I stared to feel myself nearing orgasm once again. “I’m getting pretty close Andrea.” I said. “Good.” was her reply. Andrea kept fucking me hard and I felt the pressure build. “I’m cumming!” I warned but Andrea did not slow down. I exploded as her pussy continued to ram itself around my dick. Andrea kept pounding me and I saw the mixture of my cum and her pussy juices start to run down my dick.
Andrea finally stopped when my dick had softened to be of little use to her. She leaned down and licked it clean. “So,” she asked with my dick popping out of her mouth, “think you will be able to walk?”. I smiled down at her and said “I’m not gonna be able to walk right for a week.”. Andrea smiled back. We caught a few hours of sleep and took a shower. We each got dressed and I drove her to her friend’s house. We gave each other a hug and said good bye.
The next day at school things went back to normal. Surprisingly I found that my feelings for Andrea had changed. She was still my best friend, but I did feel a new bond with her from our experience. We finished out our school year and I help Andrea move to her new dorm. Two months later I was boarding a plane, headed for Orlando, FL to start my basic training for the Navy. Andrea was there to say farewell. I gave her one last hug and she whispered in my ear “Our bet is still on there stud. Proof is still required.”. I looked at her and she gave me that special smile once again. Andrea was daring me to try to get another pair of sisters into the sack. If only she knew what awaited me on my 1st deployment to the Mediterranean Sea 18 months later.