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This story started a few years ago when I was dating Cindy, a gorgeous 38-year-old blonde. She had always reminded me of Stevie Nicks in a way. Cindy was in the process of finishing her degree at the same time that she was going through a very nasty divorce. Not very long after I had started seeing her, she lost her job and had her car repossessed. In short, she was having a very difficult time.
In order to help her out, I offered her a job. Being that we lived a fair distance from one another and she did not have a car, I started staying the night with her and driving her to school in the morning, waiting for her and then we would go to work. Spending this much time together, the relationship soon became very intense. Everything was clicking, including our sex life!
At first, Cindy was very uncomfortable with me staying over because she had an 18-year-old daughter, Nikki. She was afraid that she would be sending the wrong message to her about pre-marital sex and such. Actually, Cindy was pretty uncomfortable about sex in general, at least at first. One of the reasons for this was that she had married young and had never had a very unsatisfying sex life with her husband. She described it as “non-existent”. As our relationship grew and Cindy became more aware of what a “good” sex life could be like, her inhibitions lessened. Before long, we were openly sharing her bed.
Like I said above, everything was clicking. Cindy was getting back on her feet and we were both having the time of our lives. Things just kept getting better and better. Including our sex lives. As time went on, she became more and more adventuresome in the bedroom. It was very playful and fun. We experimented with all kinds of different things, watching videos, oral sex (both giving and receiving); eventually she even wanted to experiment with anal. In essence, she was experimenting with just about anything sexual. Which led us to experimenting with role-play.
One night before going to bed we were folding laundry and Cindy took Vicki’s cheerleading outfit out of the basket and was holding the dress up to her body as she brushed some small wrinkles out. As she did this, I let out a soft wolf whistle and teasing told her that she would look sexy in that outfit. She told me to cut it out that she would never be able to fit in it and that she would feel uncomfortable wearing Vicki’s things for my sexual enjoyment. I dropped it and we continued talking until the laundry was all put away.
Later that night, after having gone to bed, Cindy asked me if I would really enjoy seeing her in the cheerleading outfit. I told her that I would indeed! She made me promise that I wouldn’t tell anybody and slipped out of bed and out of the room. When she returned she was wearing the outfit and had put her long blonde hair up in pigtails. She looked all the part of the high school cheerleader. I called her to the bed and we proceeded to make out. I was very excited by the scene. As we kissed and petted, she asked me if she really looked like a teenager. I told her that yes she did and continued to rub her full breasts through the material of the sweater. As my hands explored her body I flipped the skirt up and rubbed on her pussy through the material of the matching panties that went with the outfit. She told me that she felt like she was a teenager making out in the back of some boy’s car. As I proceeded to undress her, I ran with that scenario and pretended to be a high school stud, making it with the hot young cheerleader.
She got into her role too. She pretended to be a nervous virgin and made me “seduce” her. Much like two teenagers in the back of a car, I went from first base to second base and then to third, where she “attempted” to stop me. I retreated and went back to the safety of second base. Kissing and sucking on her firm, full titties and massaging the inside of her thigh. Slowly, I moved my fingertips back up to where they were massaging her pussy through the thin material of the panties. Eventually, I removed her sweater completely and kissed my way down her stomach and began licking and nibbling her pussy through that same material. Between the moisture from my mouth and her pussy juices as she became more and more excited, the panties became soaked.
I pulled the elastic aside and started fingering her. First with one finger, then two and eventually three. All the time, still licking her clit area through the material. As she got into the sex more and more, she didn’t seem to notice me pulling her panties down and going to work on her clit minus the panties. The panties fell on top of the skirt and sweater at the side of the bed.
I continued to eat her until she had an enormous and loud orgasm. I then climbed on top of her and slid my throbbing member into her. With my entering her she continued in what seemed like a series of orgasms. I fucked her hard and with abandon. Unnoticed by us the headboard was pounding into the wall that separated Cindy’s room from Vicki’s. After several escort ataşehir minutes of this pace, I came and collapsed on top of her. Rolling over, I took her into my arms and we just laid there, breathing hard and recuperating. I think that both of us were totally surprised that we had gotten so carried away!
As we laid there, Cindy asked me if I had enjoyed myself. I joked with her that it had been “alright”. To which she punched me and teasingly told me that now that she knew that I was into such “younger” women, that she would have to watch me around Vicki. I told her that she was out of her mind! She said, “Right! That she had seen me checking Vicki out before. I told her that she was nuts, that I wasn’t a pedophile. She said that Vicki was 18, so it wouldn’t be being a “pedophile”. I told her that she didn’t have anything to worry about, that I would never look at Vicki that way! She said, “Bullshit! That there wasn’t a heterosexual man alive who wouldn’t at least sneak a peak at Vicki if she was wearing that cheerleading outfit.
Knowing that she was probably right, I finally agreed that if she were any other 18 year old hard body in that outfit, I probably would sneak a peak, but that would be it! This seemed to placate Cindy and kissed and rolled over to go to sleep. Later that night I awoke to the feeling of Cindy’s hand on my cock. She was jacking me off and my cock had already responded and was at it’s full length. Cindy nuzzled up to my ear and whispered, “Bobby…. you can’t tell me that if this was Vicki playing with your cock, that you would tell her to quit”. Not being fully awake, I didn’t know what to say. So, I just laid there. She continued to kiss me and play with my cock and then rolled on top of me, placing the head of my cock at the opening to her pussy. As she slid down on it, her face came to my ear and she said, “Ah come on…. Tell the truth…if this was Vicki, you’d fuck her wouldn’t you?”
As she said this she slid her pussy down on my cock and back up really slowly. I could feel the sides of her pussy gripping the shaft of my dick. She whispered in a commanding sort of way, “Tell me! You’d fuck her, wouldn’t you?” She started fucking me faster and faster and as she did, she looked me straight in the eye. This time she didn’t whisper, she told me out loud, “TELL ME you’d fuck her, wouldn’t you!”
I didn’t know what to say? I’m a kinky bastard, but this was too much! Did she really want me to tell her that I would fuck her daughter? Was this some kind of weird test? I didn’t know? I guess that she saw my indecision and she again put her mouth to my ear and told me, “It’s alright, I want you to pretend that I’m Vicki, please?” I said, “Okay” and told her, “Fuck me Vicki”. With that she moaned and went back to riding me like a horse! As we fucked she rolled off of me and I had no choice but to follow her to where I was now back on top of her. She told me to tell her want I wanted to do.
I told her, “I want to fuck you Vicki!” And, “Oh, Vicki, you’ve got such a tight young pussy! Oh God, I want to fuck you!” and things to that accord. The dirtier I talked, the more Cindy got into it. The more she got into it, the more I did too! Soon, we were banging the headboard against the wall again! As she came, she cried out, “Fuck me Bob! Fuck your little girl!” With that, I shot another load into Cindy’s tight little pussy!
Again, I rolled off of her and she reached up and kissed me tenderly on the lips and said, “Thank you! I love you Bobby”. With that we rolled over. I laid there thinking about what had just happened. After a few minutes I heard the rythmatic sound of her breathing, telling me that she was asleep. As she laid there I looked at her and then at the bedroom door, which led to the hallway and then to Vicki’s room. For the first time, I actually did imagine what it would be like to fuck Vicki.
I imagined what it would be like if it were Vicki laying there next to me, not Cindy. What it would be like to reach over and run my hand over Vicki’s firm young ass. What it would be like to kiss her. To kiss my way down her supple body, to suck on her smaller, but very nice titties. To taste her sweet young pussy. To fuck her, like I had just fucked her mom. As I was thinking these things, I got hard again. Not bad for a forty year old guy! Trying not to wake Cindy, I jacked myself off to a third orgasm of the night. Fantasizing about fucking Cindy’s sweet little Vicki.
The following morning I awoke to the sound of a light knocking on the bedroom door. Without thinking Cindy told Vicki to come in. Vicki stepped into the bedroom wearing an oversized basketball jersey as a nightshirt. I sat up as Cindy asked her what she needed.
Vicki responded that she needed her cheerleading outfit and did Cindy know where it was. As she said this, her eyes looked down at the outfit and still damp panties piled next to the bed. Before Cindy could say anything, Vicki said never mind and retreated back out the door.
Cindy kadıköy escort rolled over and told me “that’s weird. Why does she need that outfit on a Sunday?” I responded that I didn’t know. Thinking to myself that it was weird. She wouldn’t have any games or other school activities on a Sunday? I also thought to myself that it was weird that Cindy didn’t seem to have wondered what Vicki would have been thinking when she saw her cheerleading outfit rumpled on the floor next to her Mom’s bed?” “Oh well.” I thought to myself as I bent over and pulled on a pair of jogging shorts so that I could dash to the rest room.
As I closed the door to Cindy’s bedroom and headed down the hallway, past Vicki’s room to the bathroom, Vicki’s door opened and Vicki stepped out into the hall way wrapped only in a towel. Almost bumping into her, I pulled up so that she could come into the hallway. Not thinking, my eyes immediately traveled the length of her beautiful young body. Catching myself, I stopped but not before she had noticed me looking at her. I said, Excuse me! She said, “No problem!” Smiled at me and took a quick glance at my jogging shorts which did little to hide my semi-hard cock under the silky material. She then casually kind of skipped down the hallway and into the bathroom ahead of me. As she closed the door behind her, she called out, “If you need to go, use the downstairs bathroom, I’ve got to get ready”.
With that I went downstairs, wondering if I was just being a dirty old man or what? After finishing my business and washing my hands I went into the kitchen and fixed a pot of coffee. Grabbing two cups, I went back upstairs to rejoin Cindy. As I was carrying the tray up the stairs Vicki, again wrapped in just a towel with one wrapped around her hair crossed the top of the stairway. I wasn’t sure if it was my imagination or if she had really paused at the top of the stairs, but I damn near spilled the coffee as I stumbled up a stair looking at her!
Regaining my composure, I reached the top of the stairs. I looked at the closed door to Vicki’s room. My mind racing, “Is she flirting with me?” That thought combined with the previous evenings activities had my mind in a whirl.
Entering Cindy’s bedroom, she sat up and I handed her a cup. She took it and smiled at me. I went around the bed and got back in. Cindy set her cup on the bed stand and looked at me and asked, “Did I go too far last night?”
I looked at her and told her, “No, we were just playing and as long as we both enjoyed it, that it had to be okay!” She said, “You’re right. But that was intense, wasn’t it? I told her that it was and that I had enjoyed myself big time!” She said that she had too and that we would have to play that game again sometime. I agreed and started to make a move on her, saying that, “ I wouldn’t mind playing it again right now!” She just smiled at me and hopped out of bed saying, “Later, I’ve got to get going. I told my Mom that I would stop by her place this morning. Go back to sleep and I’ll be back in an hour or so.
With that, she threw some jeans on, ran a brush through her hair and dashed down the hallway to the bathroom. I laid in bed, still thinking about last night and this morning. After I heard the garage door open and close their was a knock at the door. I told Vicki to come in, which she did, still dressed in just the basketball jersey. As she bent down to pick up her cheerleading outfit one of her beautiful little titties came into view from the side through the large armhole of the jersey. She just smiled at me when she saw what I was looking at.
She stood up with the outfit in her hands and said, “It looks like you guys enjoyed yourselves last night”. I was embarrassed, but intrigued. Where was this going? I replied, “Well, we did.” She looked me straight in the eye; much more determined than I ever could have imagined a young 18 year old girl looking and said, “So, tell me, did you enjoy pretending that mom was me?”
I was flabbergasted! While I wasn’t sure what she would make of her cheerleading outfit being on our floor, I hadn’t thought of her in any way knowing what we had role-played last night! Before I could say anything else, she went on, “I heard everything! You guys had me sooooo turned on! I shouldn’t tell you this, but I played with myself listening to you two. I’m not sure who came more, mom or me!
Again, I didn’t know what to think! Here I was laying in the bed of a woman that I had really only known for about a month or two, having just fantasized with her about fucking her daughter and now the daughter was standing just a few feet away from me dressed in just an oversized basketball jersey that showed her tits every time she leaned one way or the other! Suffice it to say that I was dumbstruck!
Vicki asked me if she could sit down on the bed, which brought me out of my stupor. I said, “of course.” When she sat down the jersey rode up and I could see all the way up her leg to where her maltepe escort bayan other leg crossed it. She asked me if I enjoyed looking at her and I told her that yes, I did! She asked me if I would like her to take the jersey off? I tried to recoup and told her, “No, we shouldn’t do that” She ignored me and stood up and took the jersey over her head. Now she was standing there completely naked in front of me!
I was torn! I knew that I should put a stop to this. But I didn’t want to! I mean, really? How many 40-year-old men would kick a 18-year-old hard body out of their bed? Now, the problem was that this wasn’t MY bed. It was my girlfriend’s bed and this was HER 18 year old daughter. As I was mulling this over she slid in to the bed next to me. Her body came to rest along side of mine and her hand reached down and gently grabbed my rock hard cock. She mewed as she rubbed it through the silky material of my running shorts. She told me to tell her what happened last night. I know that I shouldn’t have, but I did. I told her. As I did, she threw the sheet off of us and slid down and tugged my shorts. Now, I could have resisted. I could have refused to raise my hips to allow them to be removed, but I didn’t. She kissed her way down my body telling me to keep talking. Soon she had the tip of my cock in her mouth and was jacking off the base.
As I finished the story, she climbed up and put the mouth of her pussy on the tip of my dick. She smiled mischievously at me and asked me if I wanted her to stop. With that, she rotated her hips which caused the tip of my cock to slide in just a little bit. I said, “No, don’t stop! With that she slowly slide herself down. Impaling her firm young body on my cock. Looking at her, the resemblance to her mother was remarkable! I couldn’t believe that this was happening! I felt guilty, lucky, excited, scared and a hundred other feelings. The most pressing of which was turned on!
Then the wildest thing happened. Just as her mother had done the night before, she rolled off of me. Knowing that I would follow! I ended up as I had the night before. Face to face with my lover. Only this time, it wasn’t Cindy pretending to be Vicki. It was really Vicki. Throwing any inhibitions that I had to the wind, I laid my body down on top of Vicki and put my arms around her pulling her close to me. Vicki’s legs wrapped around my back and she looked me straight in the eyes again and told me to fuck her!
I did! I fucked her every bit as hard as I had fucked her mother the night before! The only difference this time being that I took note of the headboard banging against the wall. As I fucked her my imagination went wild. I pictured her playing with herself last night as I fucked her mom. I pictured myself fucking her mom last night. My concentration returned to the job at hand, making love to this beautiful young woman. I didn’t care if it was right or wrong. It was way past that now. I just wanted to make her cum. I wanted to feel her, to hear her, to fill her as she came. We fucked at a frantic pace. Vicki matched me stroke for stroke. Our passion rose to a fever pitch. It was taking all of my concentration not to cum yet. Then she let loose. She screamed out, “I’m Cummmmmminnnnngggg!!!!” With that, I let loose and filled her tight young pussy with my seed. My balls pumped and pumped. Again, I collapsed on top of a beautiful woman who I had just made love to.
After we laid there for a couple of minutes we heard Cindy’s car pull into the driveway and the garage door opening. Vicki kissed me on the lips and hopped out of the bed. She grabbed her nightshirt and turned and looked at me. She said, “Our secret?” What else could I say? “Of course!”
Epilogue: I dated Cindy for about a year after this story took place. After graduating with her degree she was offered a great job in another city. We tried to make a long distance thing work, but it didn’t. We parted friends. She never knew about Vicki and I and never brought up that scenario again, though we did role-play a couple of wild ones!
Vicki and I continued as lovers off and on over that next year. There was one time she came home drunk and I was watching TV downstairs while her mom was asleep upstairs. She sat down and one thing led to another and we ended up making love on the sofa.
There was another time when Cindy had to leave town for an interview and Vicki and I had the house to ourselves for two whole days. Other than those times it was pretty much a random occurrence. We would hook up during the times when her mom was away from the house. Right after her Mom took the new job, Vicki left for college.
I sometimes talk to both of them on the telephone. Cindy is doing great on her job and is now involved with a guy that she thinks that she might marry. Vicki is having the time of her life in college and is trying to talk me into coming and visiting her. I have a couple of women that I tease with, but that’s about all. I’m still torn about what happened, but consider it to have been probably the best thing that has ever happened to me! The fact that nobody got hurt makes me happy and I haven’t made up my mind if I’m going to take Vicki up on her offer. If I do, I’ll be sure to write another story and let you guys know what happened!
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