Debbie and Her Sister

Posted in: True Stories

It was time to see Debbie again. There is something about our relationship that most people will never understand. We had an affair when we were in our mid-twenties and both of us claim that we have the best sex together. But somewhere along the way we also became the best of friends. Even though my career has moved me around the country, I’ve always been able to call Debbie and tell her the things that I couldn’t share with anyone else, and she knows she can tell me anything in complete confidence. I had just gone through my second divorce. Debbie was the only one that understood that the main reason for leaving my wife was because of sexual incompatibility, or should I say, the complete lack of sex altogether. Whenever I had an affair or a one night stand, I could tell Debbie all about it. Debbie also went outside of her marriage for sexual companionship. When we confided in each other of our sexcapades, it would often lead to us masturbating over the phone together. What especially turned me on was that Debbie is bi-sexual and hearing how she seduced another woman really turned me on and fueled my fantasies. Every time that my travels brought me close to where she lived, I’d get a hotel and she’d meet me there. It was sex like I always thought sex should be.
Since the first time Debbie rocked my world, I kept looking for someone who I was sexually compatible with, someone who met up to the standards that Debbie had set. I had gone through two marriages, several relationships, and a couple of drag down, knock out affairs. A few came close, but I wanted the complete package and it just wasn’t there. So after my last divorce, which broke up because of a year long affair I was having with a co-worker, I took a promotion and moved to a new city. It was closer to where Debbie was living and she was excited that she would see me more often even though I knew she would never leave her husband and kids. After settling down in my new place, I went to see Debbie. She met me in my hotel and from 10am until 4pm we picked up right where we left off. We both tried to act non-chalant about being together again, but after a couple of drinks, a joint, and watching some porn, it didn’t take long for her hand to find it’s way into my pants and for me to take off her top and bra to expose the big full set of tits that constantly drove me insane. This was sucking and fucking at it’s finest. She had to be home by 5 when her husband got off of work, but she said she would be back later that evening. I don’t think anything will ever exceed what happened that night, it was a once in a lifetime event. If I ever need arousing, all I have to do is think about that time.
Debbie called me soon after she got home to tell me that her husband had to unexpectedly go out of town on business and wouldn’t be back for a couple of days. As soon as he packed his suitcase and left, she would be right over. We were both ecstatic and I thought maybe I’ll even get to sleep with her. I could just imagine waking up with her sucking on my early morning hard on. In what seemed like an eternity, I finally heard a knock on my hotel room door and I let Debbie in. I dropped my pants and flashed my cock, and Debbie lifted her top to expose her wonderful 38DD’s. We laughed, and as I poured us a drink, Debbie told me that her older sister, Paula, was in the car. She wanted to know of it was ok if she joined us for a while because her boyfriend had just broken up with her after a long relationship. Sure, it was ok with me. I thought meeting a member of her family would bring Debbie and I even closer. I asked if Paula knew about us, and Debbie said that she did know about me, “But not everything, if you know what I mean.” At the time I was wearing a pair of gray flannel shorts and a white tank top t-shirt and I mentioned that I should probably change clothes, and Debbie remarked, “No, stay dressed just as you are. I know it will drive Paula crazy!” A couple of minutes later I met Paula when she walked into the room.
Paula and Debbie don’t look anything alike. Debbie is a short brunette and Paula is a tall blonde. Even though Paula had on a baggy, loose fitting top, I could tell that she did inherit the same boob genes that Debbie had. Paula was somewhat reserved at first, sitting at the end of the sofa with her feet curled up underneath of her. Debbie was on the other side of the couch, and I sat in an easy chair across from them. At this point in time, I was glad that I got the suite in this hotel because it did offer a homely type of accommodation. Debbie and I still had a buzz and we were carrying on. After a drink and a couple hits of pot, Paula began loosening up and joined in. She was very attractive but one thing I noticed about her was her mouth. When she smiled it filled up her face, a wide grin with slightly puffy lips. What I called the perfect cock sucking mouth. We had finished the half bottle of scotch that I brought with me, Debbie said that she would go to the liquor store and get another one, leaving Paula and I alone. Debbie gave me a knowing smile as she left and gave her big tits a squeeze when she knew Paula couldn’t see her. Christ did she know how to make me horny and I just wanted to fuck her all night.
When Paula and I were alone, she said that she knew that I just went through a divorce and went on to explain her recent break up in a long term relationship. “How do you deal with that?” she asked. “One day at a time,” I replied. I went on to tell her that it was my idea to break up, where in Paula’s case it was her boyfriend’s insistence to call it quits. When I mentioned the lack of sex in my case, Paula didn’t hesitate to say that her sex life was great, she took care of her man, and she couldn’t understand why he left her. I could tell that she was devastated over the whole situation. I went on to tell Paula about my first wife and I had left her for another woman because the sex was great. When the other woman broke up with me, because she had to go ‘find herself’, I was in the same state that Paula was in now. I said, “If it wasn’t for your sister, I would have gone crazy. She has been my best friend for the last 15 years with all the crap I had been through.” An hour before I could tell that Paula was giving me the once over, like the protective big sister making sure that Debbie wouldn’t be hurt. But now Paula said she could see why Debbie liked me and, in her words, “I think you’re pretty cool. I just wish I was in the same mental condition that you’re in right now.” I replied, “Given time, I know that feeling will pass. You’re a very attractive woman, I know you’ll meet someone else.” Paula thanked me for the compliment and said, “You’re a handsome man yourself, I bet you don’t have any problems meeting women.” All I had been thinking about since they showed up was how long would it take before I was going to get Debbie in bed again. But somehow there were now sparks flying between Paula and I. I began wondering what she looked like without any clothes on and if she was as good in bed as Debbie. In a rather bold move, I said to Paula, “Well, I know I could make you forget about your boyfriend at least for one night.” A half crooked, sly type of smile came over her face and she seductively said, “What do you men for one night?” and she took a sip of her drink. I rose out of the chair and walked over to Paula. She stared at the bulge in my gray shorts and licked her lips as I closed the distance between us. I sat on the sofa next to her, she put her hand on my thigh, and as I moved my face towards hers I said, “This is what I mean,” When my lips met hers, her mouth was already open and waiting. I put my hand around Paula’s waist and she pulled her body into me. What a kisser, our tongues were immediately flying in each other’s mouth. I could tell she was man hungry and her chest was pressed tightly into mine. Paula leaned into me hard, pushing me on my back and she was on top of me without breaking our mouths apart for even a second. My hands rubbed Paula’s back all over and soon found their way to her nice firm ass. When I squeezed her buns, Paula moaned in my mouth in approval. My cock was now hard and I could feel the heat and moistness coming between her legs through her jeans. The passion kept increasing between us and I always love the first kiss, especially when the other kisser wants it just as bad as I do. I reached up and massaged the side of Paula’s breast as it flattened against me. I could tell her tits were as large as Debbie’s, maybe even bigger. Again, Paula moaned and increased the motions of her crotch as it rubbed against mine. She broke the kiss, raised up on her arms, and looked down at me. “Wow, this is nice. You’re making me feel so good.” I took advantage of her position and reached up with both hands to feel just how big her bra covered tits were. They were as big as Debbie’s and all I could think about was having her nipples in my mouth. It was turning Paula on and she kept sliding up and down against my very hard cock. I reached up under her shirt and felt the filled up cups of her lacy bra, my hands barely able to cover half of them. Paula smiled at me below her, and she fell back on top of me, kissing me even more passionately with my hands pinned between us. At that moment I thought that Debbie would probably be back soon, and there was a knock on the door that startled both of us. “Shit,” Paula exclaimed, “She’s back already.” She got up off of me and I asked, “Can you answer the door? I’m, uh, kind of in a compromising position.” Paula saw my big cock poking up through my shorts and laughed. She reached over and gave my erection a squeezed and said, “No problem. But how are you going to explain that!” I sat in the chair and crossed my legs to hide the obvious. Debbie came in with a bottle wrapped in a brown paper bag, the lid was already unsealed and I knew she had a couple of swigs on the way back to the room. After an awkward moment of silence, I said to Debbie, “Hey baby, pour me a drink. I think I need one really bad right now.” Debbie glanced at me and replied, “Well, I just hope you two weren’t doing anything I wouldn’t do while I was gone.” I know all of us thought that left the door wide open for just about anything. I was left somewhat confused, who was I going to end up with for the night? I just knew what ever was going to happen, would happen. I just hoped that neither Debbie nor Paula would get pissed off me.
Over another couple of drinks, Paula kept prodding and asking, and it soon came out that Debbie and I admitted we were having sex. Paula was not judgmental at all, and in a way she knowingly approved. Then Debbie recalled a time when she was still in high school when Paula and her got stoned and swapped boyfriends one night. Paula laughed and said she had fun, and with that I could tell that Paula also had the same openness with sex that Debbie did. When Paula asked how we first got together, I told a familiar story. My first wife and I, along with Debbie and her husband, got high one night and played strip poker, but nothing happened and we quit before anyone got totally naked. “But,” I added, “When the other two weren’t looking, I flashed my cock at Debbie and she showed me her tits.” A couple of weeks later, we were drinking Jack Daniels and smoking pot at my place after a night out, and we started playing strip poker again. This time we went all the way until everyone was naked. Debbie won the last hand and told my wife to suck on her husband’s nipples. My wife didn’t hesitate one bit, and Debbie grabbed my hand and said, “Let’s go into the bedroom.” The rest, as they say, is history. When I finished telling the story, Debbie asked Paula to join her in the bedroom, obviously where I couldn’t hear them talk. When they came back, Debbie asked, “How would you like to play strip poker again?” “With you and Paula?” I asked back. Paula was already sitting at the little dinette table that the suite had in it, and she said laughing, “Yeah, don’t worry. You won’t turn us into deviates. We’re already there!” “And horny!” Debbie chimed in, “I’ve got a deck of cards in my car, I’ll be right back.” When the door shut behind Debbie, I stood next to Paula, leaned down and kissed her again. When I started to rub her tits, she pulled my hand away saying, “Not so fast there stud. Take your time.” Debbie came back with an overnight bag that she had packed when her husband left to go out of town. She sat at the table with us and I poured a very strong drink for myself. We set the rules, whoever won the hand had to take a shot of scotch, take off an article of clothing, and tell the other two about some moment of sex that they had in their past. I was put at an immediate disadvantage having only my shorts and t-shirt on. The girls had their tops, their bottoms, panties and bra. But right now it didn’t matter, I was ready to get naked, and it didn’t bother me of they were sisters if it didn’t bother them.
Debbie won the first two hands and was down to her bra and panties. Paula won the next hand and took off her top. There in front of me were 4 nice, shapely bras filled up with some rather large tits. I began to get an erection. The quick stories that they told we pretty exciting as well. All of us ended up taking a shot of booze anyway. Then I lost the next two following hands. When I took off my t-shirt, Debbie started rubbing my nipples which she knows turns me on. When I lost my shorts, Paula remarked, “Let’s see if its as nice as Debbie says it is.” I stood up and dropped trou, my half hard cock pointing straight out about 7 inches, and Paula sighed under her breath. “Wow, Debbie. That is a nice one that you’re getting fucked with.” Debbie had to take off her bra next, and she wasn’t bashful about it at all. She shook her big bare tits all around once they were freed my mouth began to water. She took her nipples between her fingers and tweaked on them, making them hard and poke out as I dealt the next hand while Debbie told of a story where one of her girlfriends fucked her husband just so she could have sex with her. Paula won the next hand and when she hesitated to take off her bra, Debbie was almost ready to rip it off of her. Paula pushed Debbie away and slowly revealed her ample bosom. Where Debbie’s tits are pear shaped, Paula’s where round and very firm. Debbie has dark red nipples, yet Paula’s were taught and pink, centered perfectly in the middle of her orbs. As I stared at them, and getting harder by the second, Paula cupped her breasts from underneath to proudly display them saying, “Do you like my tits?” All I could respond with was, “Wow, Paula. Nice rack.” She knew she had man pleasers and had this proud look on her face. I won the next hand, and I didn’t have any clothes on. Debbie said, “Ok, let’s see you play with your cock. I like it when you play with your cock.” I grabbed my cock by the based and cupped my balls in my hand. As I shook it around, I saw Debbie’s hand go between her legs. Paula stared with a half open mouth. As I did this I told Paula, “Earlier today, after I fucked Debbie for the second time and made her cum, she started to go down on me. She grabbed my hand and made me jack off in her mouth while she rubbed her tits in circles. After I came, she spit the cum all over my crotch and it was such a turn on.” It was Paula’s turn to deal and she quickly shuffled the cards saying, “Christ, I just want to get naked.” In rapid succession, both Debbie and Paula were now totally nude. When Debbie dealt the last hand she said, “Ok, whoever wins this hand gets have their way, any way they want it.” There were no objections. I’ll never forget that hand. I had two pair, Kings high. Paula had 3 Aces. Debbie had a full house Queens high and she raised her hands in victory like she just won the lottery. When she settled down she looked at Paula and I in all of our splendor and naked glory. “Ok, now I want to see you two have sex while I watch.” She reached into her overnight bag and pulled out a dildo that she nicknamed Joey, then said, “Let’s go in the bedroom.”
Paula didn’t waste any time. She shoved me down on the bed and climbed on top and while we kissed she rubbed her slit up and down my pole. I looked over at Debbie who was sitting in a chair next to the bed and giving me a show. Many times she would use her dildo when we had phone sex and I always want to be a fly on the wall to watch her while she masturbated. She sucked on the fake cock, squeezed her magnificent boobs around if, and was running the head up and down her pussy. When she spread her legs wide apart I knew she was going to put it inside of her, and at that time Paula said, “I think I’ll just slide it in.” She took the head of my cock inside her pick folds of flesh, bobbed and down on me a few times, then thrust her hips until I was all the way inside of her. As I let out a long satisfied moan, Paula said, “Oh yes, that’s it. My oh my, that is so nice. It fills me up so damn good.” One thing that I liked about having sex with Debbie is that she is very vocal, and it seemed immediately that Paula had that in common with her. I reached for Paula’s tits and as she hovered above me. I gently sucked on her nipples which made her shiver. She closed her eyes and rocked on me, her clit rubbing against my pelvic bone, and with one of her big tits smothering my face I began to massage her silky smooth ass. It didn’t take long, and when Debbie said, “Fuck him Paula, fuck that big cock. Fuck you two are turning me on.” I looked at Debbie again, she had the dildo going in and out of her cunt faster and faster. She was manipulating one of her big tits, pinching and pulling on the nipple, and she had that look on her face like she was going to get off. When she closed her eyes and all of the blood rushed to her strained face, the veins popping out on her neck, I knew it wouldn’t be long. At the same time, Paula was circling her clit over my crotch and her breathing became more rapid. Somehow, I wasn’t close to cumming yet, and within moments of each other they both started to orgasm. Paula was screaming, “Squeeze my ass, suck my tits. Harder, harder. Oh yes, that’s it, oh fuck yes.” Debbie was shouting out, “Oh yeah, oh yeah,” over and over. Just as fast as it seemed to start, both of them came just as fast and in a little bit it was over until they regained their senses. When Paula finally opened her eyes, I rolled her over and got on top of her. I just had the burning desire to fuck her until I came with Debbie watching. I drilled Paula for all I was worth, her legs shooting straight up in the air as she held on to her tits for dear life. Debbie got out and moved behind me, rubbing her tits against my back and my ass, then reaching around to rub my sensitive nipples. As Paula moaned and groaned out loud, Debbie was urging me on, telling me to pull out of her so she could see my dump my load. After about 5 minutes of this I couldn’t hold back any longer, Debbie and Paula had me so fucking peeked out that my balls tightened and I announced that I was going to blow my wad. I pulled out of Paula and kneeled between her spread legs. I grabbed one of her ankles and with the other hand I started to jack off my sperm. Debbie leaned over my shoulder to watch, and even though I had cum twice earlier with Debbie, I let go of a huge load. My gooey jism streaked all over Paula’s chest in load after load as she watched in astonishment. When my hand started so slow down after a dozen shots, Debbie moved around and sucked the last few drops out of my prick. The feeling was like nothing I had ever felt before, usually I would try to pull her off of me, but I let her keep sucking and my head was spinning. When my cock finally went flaccid, Debbie spit it out and I could barely speak. I laid down next to Paula, held her in my arms, and finally the passion of having sex with Paula swept through me. When I opened my eyes, both of them were just staring at me and I could only say, “I think I need a fucking drink.”
The hotel suite was equipped with a hot tub, not very big, the three of us could fit in there but we’d be real close to each other. We sipped on a cocktail, took a couple hits of pot, and relaxed in the warm, swirling water. Under the water, Paula had move her hand up my thigh and started playing with my cock in a way that Debbie wouldn’t notice. Then Debbie started rubbing my other leg and when her hand reached my crotch, she laughed when she found Paula’s hand already there. I thought that after cumming three times today that it would take me a little while to get another erection, but the whole situation was making me horny again. I began rubbing their tits and my brain was willing my peter back to attention. Debbie leaned over and began sucking on one of my nipples. Paula watched for a moment, and as I grew harder in their hands, she leaned over and started sucking my other nipple. I was now completely hard, and I lifted my ass up in the air so you could the result of their efforts. Paula leaned back a little to see my condition and she was pleased. With Debbie still sucking on my nipple and cupping my balls, Paula lowered her head and started to suck me into her mouth. I’ve had my share of blow jobs before and Debbie was always the best, by far. Yet Paula had her own style and her mouth felt like velvet as she bobbed up and down on me. Debbie watched, her fingers taking over where her mouth had just been, and she remarked, “I think I need some of that.” Paula lifted her head up off of me for a moment and replied, “I need it worse. You already fucked him twice today.” That kind of settled the argument as Debbie didn’t say a word. Paula climbed on top of me and lowered her snatch on my cock. She slowly bounced up and down and Debbie said, “You know, these jets put out a lot of pressure.” She positioned herself so one of the jets was pulsating on her pussy. I had her tits in one hand and Paula’s tits in the other, then I just buried my face in Paula’s chest. When I came up for air, all I wanted to do was bring as much pleasure to Paula as I could. I whispered in her ear, “It would make me very happy if I could just eat your pussy right now.” Paula stopped her gyrations, she smiled broadly and put her hands on the sides of my face. “Wow!” she remarked, “You are a good lover!” The water of the spa was keeping Paula’s cunt from being moist, so we jumped out and went to the bedroom floor. I laid her down and spread her legs, kissing and sucking up and down her thighs. When I came to her pussy and started to lick her slit, Paula let out a long low guttural moan and moved her hips up to meet my face. I was making love to her with my mouth, giving her everything I could to make her feel as good as possible. It was working, Paula begged me not to stop, and all of a sudden I felt Debbie sucking on my cock. Debbie concentrated in the head of my cock, sucking on it hard and rolling her tongue around the rim with a firm grip on my shaft. She is the best, and if I hadn’t been concentrating so hard on Paula, I probably would have unloaded in her mouth. I zero’d in on Paula’s clit and she was squirming around on the floor. “Oh yes you motherfucker, suck on me. Oh fuck it feels so good. Please don’t stop. You’re going to make me cum again you bastard.” I stuck two finger inside of her, searching around until I found her g-spot. I massaged her little bulb while licking, sucking, and moaning on her clit. “Oh fuck yes, yes,” she said loudly. Her body went rigid. I looked up and she was pulling on her big tits. She held her breath deeply and then let it out as she started to squirt all over my face. Then she squirted some more, gushing out her fluids, covering my head with her juices. It was like the dam broke, and her body was twisting and turning to the point where I had to hold onto her ass to keep my mouth between her legs. A lot of her cum ended up in my mouth and I swallowed as much as I could. Debbie had stopped sucking my dick so she could watch the event. When Paula finally stopping cumming, Debbie remarked, “Oh my God, that was incredible.” Paula’s body went totally limp as she tried to catch her breath. I was on my knees staring down at her and feeling quite proud for getting her off. Debbie moved beside me, her arm around me, and we were both watching Paula in her pure ecstasy. We looked at each other at the same time, and as if by instinct, I was in top of her burying my prick as far inside of her as I could. As I picked up the pace, Debbie started to rub her clit. I urged her on, pounding in and out of her as hard and fast as I could. Debbie was running her fingers in circles around her clit just as fast as I was fucking her. “Oh you son of a bitch, you’re going to make me cum again.” I planted my cock as far into Debbie as I could, and her body jerked uncontrollably as each tic swept through her. Moments later, both women were laying on the floor beside each other in a state of semi-consciousness. I was left with a hard on pointing to the sky, but the last thought I had right then was getting off. I felt just as content as they did.
I went back to the living room of the suite and my erection would not go down. I thought this must be what Viagra is like. I poured another drink and in a few minutes Debbie and Paula joined me with smiles on their faces and both of them constantly looking between my legs. Paula sighed and Debbie said, “Mmm, mmm. That does look so good.” I grabbed my cock in my fist and slowly started to rub it up and down. Debbie, while smoking a cigarette, started playing with herself, alternately rubbing her tits and her pussy. Paula was sitting Indian style and just gawked. Debbie then said, “Get it off. Jack it and let us watch you make yourself cum.” I knew this was always a turn on for Debbie and I replied, “Keep playing with yourself too and it won’t take me long to get there.” Paula moved over and sat next to me, tracing her finger across my chest and stomach and said, “Let me see you shoot it all over here.” I grabbed onto on her tits and picked up the up and down motion on my cock. Paula leaned over and started sucking my nipples at Debbie’s suggestion and also massaging my balls. I started at Debbie, who was smiling wide and putting on a show for me. When Debbie put both hands on one of her massive boobs, brought it to her mouth and started sucking on the nipple, I knew that it wouldn’t take much longer. I started rapidly jacking off, and I soon announced that I was going to blow my load. Paula lifted her head off of my chest to watch and Debbie moved between my legs, rubbing her tits against my thighs with her open and waiting mouth hovering over my cock. I squeezed Paula’s tit hard, and she responded my crunch my nuts just as hard between her fingers. I blew the first two loads right in Debbie mouth and is dripped all over her lips and chin. The next couple of loads streaked across my stomach and both of them we intently watching the cum spurt out of the little hole. When I stopped cumming in my cream filled hand, Debbie went down on me and Paula started licking up my juice. I was breathing very hard and I felt like the most fortunate man in the world having two very sexy woman pay that much attention to me having an orgasm. I lay down, my head in Paula’s lap and Debbie massaged my whole body. It didn’t take me long to drift off into slumber.
I woke up in the middle of the night and both of them were gone. I found a note on the table saying that they had to go and would be back tomorrow. Paula showed up alone saying that Debbie would be back tomorrow before I left. I found out that Paula really liked anal sex. She was really wild, acting like she would never have sex again. When she left around 6pm, I thought I was sexed out until Debbie showed up. Late that night we went skinny dipping in the hotel pool and we got caught by the night watchman who was pretty cool about it, probably because he got to see Debbie naked. That got both of horny all over and we screwed all night, and then the next morning until I had to check out of the hotel. When I got home that evening, Paula called me and she’s coming to visit me next week. I guess since Debbie is married, her sister will do just fine!

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Debbie and Her Sister, 9.5 out of 10 based on 2 ratings

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