Two years ago I had a girlfriend named Robin. Soon into the relationship I met her younger sister, Beth, and immediately I had the hots for her. Robin was very pretty but Beth was prettier. Robin was good in bed, but she was reserved and not as sexually driven as I was. Our sexual relationship soon fizzled to a low burn, and I imagined that Beth was more adventurous when it came to sex.
Beth was 26 then, thin, tan, with strong, runner's legs, short brown hair, firm breasts, and a delicious bubble butt. She had an athletic, bouncy personality that exuded sex. She was always swimming, running, playing tennis, being active. Robin didn't like to leave the house. When we had sex it was pretty predictable. This was my fault as much as it was Robin's, but we both began to loose interest in trying. Beth was always enticing. She would sit with her legs apart or her knee up, even sometimes in a skirt, flashing her panties as if it was all normal and acceptable. I was constantly horny around Beth, and I think she knew it. It was especially her butt that attracted me and entered my masturbation fantasies, and I felt that she, sensing this, was always pushing her ass in my direction.
Beth and I had had a mild flirtation since the beginning. Mostly it involved sexual innuendo, some sexual conversation, sometimes blatant, and glances at each other when we were all at the beach. Robin participated excitedly in the discussions but would close down when we got to the bedroom.
Beth would wear revealing clothing, and I would stare. She would traipse around in just T-shirt and panties, and I would stare. She would leave the bathroom door ajar when she peed, and I would stare. I also noticed that Beth would stare at my cock sometimes, especially when it was semi-hard at the beach. Robin either didn't care or ignored it all. The whole family seemed to disregard Beth's behavior with a shrug as if, 'Well, that's Beth.'
Last summer, toward the end of our relationship, Beth came to visit Robin and me for a weekend at the beach house we were sharing. Robin and I had been seriously discussing whether or not we were going to stay together, although no one in her family knew this at the time. It was the last time I saw Beth before Robin and I broke up that September.
Beth was recently single that summer, having endured a difficult breakup. We all swam in the ocean that day, and Beth was looking particularly sexy in her red bikini, which pressed up nicely against her crotch, clearly outling the prominent lips of her pussy. All afternoon we listened to her talk about her horrible ex-boyfriend and her nonexistent love life. Listening to her complain all day about not having sex, I was fixated on her sweet ass, imagining fondling and kissing it to make her feel better. I knew that Robin was depressed, thinking about the possibility of our own breakup. I felt the same way. But she sulked quietly and listened to her younger sister in silence.
We stayed up late that night and Beth began to complain more openly about her lack of sex and to confess her sexual needs to us both, including revealing her fantasies, which involved having two or three cocks at once. Robin was rolling her eyes. Beth also said she loved anal sex. Robin said she would never try it, that she didn't even allow my finger there. Since I was an ass man, this was a contention between Robin and me. Beth said she should not knock it until she tried it and that she bet I wanted to do it with her. Robin told her it didn't matter, that it would never happen. I felt the finality in her voice. Beth looked over at me and said 'Poor baby.'
Beth then confessed that she had been particularly horny that summer since her breakup. She said she liked a finger or cock in her ass on occasion. She also said that she masturbated often, even at her desk at work (she claimed that she learned to do this in boring high school classes). I really perked up here, imagining Beth masturbating as a high school student. While sitting at her desk, Beth said, she would pull her jeans up into her crotch and apply pressure to her clit against the seam of her jeans. Or she would pull her underwear under her skirt up into her crotch. 'All I have to do is cross my legs and rock in my chair,' she said. 'It takes a long time to cum, but it is worth it.' She confessed to having masturbated that morning just before we went to the beach. 'That's why it took you so long to get ready,' Robin scolded her. Listening to Beth made me very aroused, but I tried not let on how much I wanted to fuck her right then and there at the dining table.
Beth went on to tell us that, talking about sex all day, she was in desperate need of a 'hard cock.' She said how lucky Robin was because she always had one 'at the ready.' Little did Beth know that our sex life was anything but hot at the time. Beth said, rather sarcastically, that the only thing men are good for is fucking.
Robin was clearly annoyed. She took some dishes into the kitchen. When she was gone Beth looked at me imploringly and said something like: 'Do you think I am pretty? Do you think guys would want to sleep with me?' I tried my best to be enthusiastic without openly encouraging her or causing more problems between Robin and me. I said quietly to Beth, 'Of course I do. You are very pretty. Who wouldn't want to have sex with you? You have a perfect ass.' 'You like my ass?' she asked, 'What do you like about my ass? What would you want to do to my ass?' I did not know if I should take her questions seriously, but I decided to speak up, since she had been so sexually open. I told her that I was an ass man, that I loved the shape and curve and tightness; the cheeks, the crack, the bounce; everything about her ass, even what I imagined to be her beautiful, little, puckered hole. (She yelped when I said that.) I went on to tell her that I would love to kiss and to lick it.' 'Analingus, I love that! What else?' Beth asked. She was obviously teasing and toying with me. But I didn't care. I told her that she had a perfectly fuckable ass.
She smiled at me, like she had gotten what she wanted. Then she changed the subject. 'What else is perfect about me? I need some encouragement right now.' I told her that she had a beautiful face and that her whole body was perfect. 'Do you think guys would want to eat me out? I love to be eaten out,' She said. I was putty at this point. 'Definitely,' I said, practically drooling. I knew she could read by my expression that I desperately wanted to fuck her, but Beth just turned away, ignoring me, and sighed, like I didn't understand her frustration. She grinned. Either I had or hadn't passed her weird test.
'All men are exactly alike,' Beth said, as if disgusted. Robin had just walked into the room. 'How are all men exactly alike?' Robin asked. 'All they think about is sex,' Beth replied. 'You are pretty sex-obsessed yourself,' Robin told her. 'That's true. I am just as bad as guys.' And Beth looked directly at me, smiling.
The conversation got heated from here on out. Robin is no prude, but when Beth began to demand details from her and me about our sex life, Robin, after answering some pretty explicit questions about our favorite sexual positions, the size of my cock, if I am good at eating pussy, told her it was time to go to bed. Robin and I helped Beth to her bedroom, with Beth trying to hug me goodnight a little closer than Robin was comfortable with.
When Robin and I went to bed, I was very horny. But Robin was not in the mood. Thinking of Beth's ass and comments and questions, I tried to masturbate, but my mind was too confused and before I could cum I fell asleep with my cock in my hand.
The next morning Robin got up early to run errands and go to the gym. She told me it might be nice for me to bring Beth some coffee and aspirin and to offer to give her a head massage, as we had a lot to do that day.
Now this request may sound weird, but Robin was proud of my skills at massage. I had practiced shiatsu (acquiring only minimal skill) when I was learning martial arts. We were taught pressure points, not only how to use them to hurt but also how to use them to heal. After I showed Robin that I could massage away cramps by rubbing points on her hands and feet, she was pushing my 'magic' hands on her sister and girlfriends.
Almost always before, Robin had been there while I was rubbing another woman, including Beth. Thinking about going to Beth's room alone made me horny, but I tried not to entertain any sexual ideas. I brought Beth juice, water, coffee, and aspirin. She was drowsy and apologetic for the night before. She took the aspirin and drank the water. She said that she was feeling fine. I asked her if she wanted a head rub. She said 'Mmmmm, that sounds nice.'
Beth was on her stomach. I sat on the side of the bed and began to rub her head and neck. I was wearing thin, light blue, summer-weight pajama bottoms (no underwear) and a T-shirt. Beth said she needed to go pee. She got up and I saw that she was in skimpy panties and a T-shirt. She wiggled her ass as she walked. When she came back she lay down on her stomach and I rubbed her shoulders and back under her shirt. She asked me if I was going to rub her legs, since I seemed to be heading in that direction. The thought immediately made my cock twitch.
I pulled the sheet down to her ankles and rubbed lower on her back, then down across her butt cheeks. She moaned when I touched her ass over her white, silky cotton panties. I lingered there, rubbing her cheeks and even the crack of her ass down to the tip of her tailbone just above her asshole. She especially liked this. I then went down to her feet, worked there, and then worked my way back up to her shoulders. I spent a lot of time on her thighs, especially her inner thighs, which made her legs part. Rubbing her thighs high on her legs, I felt her pubic bones against the sides of my fingers, and I squeezed her thighs then went back to her ass. I could see the rut of her cunt inside her panties. It was a beautiful sight.
By then, thirty minutes into the massage, I was groping her ass as much as massaging it. I was squeezing each cheek, pulling apart her ass cheeks, rubbing my hands across her butt and crack. Her breathing quickened. She asked me if I still thought she had a perfect ass. I said that I did. Then I went back to her bare legs. When I came back up to her ass cheeks my fingers accidentally slid just inside the bottoms of the leg openings of her panties. I apologized and pulled them out. She said that it was fine, that my hands felt good against her skin.
What happened next seems to be almost like a dream. I went ahead and pushed my shaking hands all the way inside her panties, cupping each cheek and squeezing, pulling, and rubbing. I looked down at my cock, which was hard in my pants, and saw that a clear, precum wet spot was visible. Then I looked down between Beth's legs and saw that an oval wet spot the size of an egg was visible on her panties at her cunt opening. I trembled. This made my hands shake even more. As I pushed my hands around on her ass under her panties, she opened her thighs a little more, as the wet spot widened. Then she said 'Higher.' So I pushed my hands up higher on her ass, which pulled her panties, held tight against my wrists, up farther into the crack of her ass, exposing more of both cheeks to me. When I got to the top of her ass she said 'A little higher.' My hands exited the waistband of her panties, causing my wrists to pull her panties even higher into the crack of her ass, exposing everything but her asshole to me. Basically, I was giving Beth a wedgey.
Beth's breathing was now low but quick. She sighed or moaned every so often. She opened her legs more, pulling one leg up and bent at the knee. I had a great view of her dampening pussy. I just pushed my hands up and down from her ass to the small of her back. I squeezed and rubbed her cheeks and her thighs, spending a lot of time high on her thighs so that the sides of my thumb or pinky finger was just touching her pubic bone and the outer lips of her pussy. I even ran my hand back down inside her panties, rubbing her crack down to the tip of her tailbone. She seemed to rise to my finger, as if she wanted me to go deeper to her asshole.
I had a great view of Beth's ass, and her panties were now like a thong between her cheeks. She said 'This feels great.' It was then that I noticed that she was raising and lowering her hips slightly to the rhythm of my hands. She would press downward into the bed or raise or lower her hips to get the most pressure against her ass and pussy.
Then I decided to push it further. I took my hands off her ass and began to twist her panties so that they became a thick, rope thong wedged into her ass crack. I waited. She didn't say anything. I kept twisting the panties until they began to disappear between the lips of her pussy. She was still, but as the panties went farther into the crack of her ass and cunt, her legs opened more and she seemed to adjust herself. I said 'Now, that's better. Your panties were in the way.' She replied with a low, breathy 'Yeah. It is. They were.'
I began to rub her ass and lower back more, pulling her panties up into her ass and pussy, trying to get a view of her pussy lips, the sides of which were a little exposed. She was now really into the rhythm of my pulling; squeezing her thighs together around the rope of panties, which were digging between her lips. I think we were both frustrated. At times I lifted the panty rope out of her ass crack and down, exposing most of her ass to me, including he asshole and, at one time, the beginning of her swollen pussy. I wanted more contact and so did she. I pulled the rope up high, wiggling it and rolling it against her. At one point I practically lifted her off the bed.
Beth opened her eyes, to my knowledge for the first time during the massage, and looked right at my hard cock, which was only a foot or so from her head. Her eyes were wide and she said 'Let me roll on my side.' I took my hands off her ass and she rolled on her side, facing my side of the bed, so that she was looking directly at my cock and the precum wet spot. She bent and lifted one leg so that her open crotch, with the rope of panty rising out of her ass and wedged between her lips, was exposed to me. Then she asked me to massage her some more. I reached around behind her and put my hand on her ass, squeezing and kneading her hot cheek. She said 'No, through here.' And she pulled my arm between her legs and put my hand directly on the rope of panties wedged between her ass cheeks. I pulled the rope, and my arm brushed against her pussy and ass. I applied pressure with my arm, which she pushed against. Then she began to twist the front of her panties into a rope to match the back. I watched as the rope got smaller and tighter and disappeared between her cunt lips, exposing more of her delicious pussy to me. She had her eyes fixed on my cock as she twisted the panties and pulled them. The panties rode right up into her pussy, covering only her clit, asshole, and wet, coral opening. Then, as she grabbed the rope in front, she told me to 'Pull' on the back. Soon we were sawing the panties up and down against her asshole, pussy, and clit.
Watching her masturbate, helping her to masturbate, was too much for me to take. I reached down with my right hand and pulled my cock out from the pee slit in my pajamas. It sprang free and jumped to attention, and I began to stroke it. She stared at my cock, as she rocked and bucked against the sawing movements of her panties. 'Don't stop the massage,' she said, breathing heavily, 'Keep massaging yourself, too.' I spat on my hand for lubrication. Then she announced 'I'm almost there.' With that, I began to stroke my cock faster, almost violently, and said 'Me, too.' She came, bucking fiercely against her panties, pulling them up to her belly button. I pulled them up as high as I could in the back, nearly lifting her off the bed. This ripped the panties, exposing her whole pussy to me. Beth spread her legs wide and lifted her hips off the bed. She pushed her hands to her cunt, fingering and rubbing as she rode each convulsive spasm.
My hand slid down to the crack of her ass and I slid a finger inside her asshole, as she let out another stifled scream. Fingering her ass, I came, ropes of cum landing all over me and the bed. She was breathing hard, as she curled up into a ball with her eyes closed. I rubbed her bare ass for a while, sliding my hand between her cheeks and along her asshole. Then I slipped my finger down inside her cunt. She opened her legs wide and then she pulled my finger deeper and squeezed it with her cunt muscles. She let me finger her leisurely for a few minutes, as she rubbed her clit lazily. Another small orgasm welled up and she shook. Then she pulled my finger out and told me she needed to get some more sleep, and that I should probably leave now. She thanked me for a wonderful massage. I covered her with the sheet, kissed her on the forehead, and left the room.
When Robin got home she asked Beth if I had given her a nice head rub. 'Yeah, it was great. The best ever,' Beth replied. Then we went to the beach for one last swim. Robin told me later that while swimming she had confessed to Beth that we were probably headed for a breakup. Robin told me indignantly that in response, all Beth could find to say was, 'Oh, that's too bad. He gives such great massages.'