When Freinds With Benefits Gets Friendlier

I have known a woman I'll call Jackie for years. We met in elementary school. We continued our friendship through High school. I would go to her house regularly. Her family was into sports and staying fit and her three brothers were large and played college football. They had a work out room with mats and weights, benches, and equipment.

So Jackie and I would exercise together. Her mom and dad would often be working out at the same time. Jackie wore leotards and tights and her mom would wear a leotard but not the tights. After every exercise her mom would stand up, stick her fingers in the leg band and stretch the material out then let it snap back on her ass.

Then go to the front leg bands insert her fingers. Run them up and down, stretch the material out, allowing me to see her close trimmed red pubic patch before letting it snap back over her pussy, clearing the camel toe from the work out. I tried not to look but it was impossible. I was afraid her large husband would grind me up from jealousy. But he just smiled real big as he watched me. It drove me crazy and everyone knew it. I seemed to be the only one who wasn't amused. It always gave me an erection that I had trouble hiding.

On occasion mom and dad would go out of town. Then Jackie and i would exercise nude. My favorite was sit-ups. I had no idea how tight pelvic muscles would get during exercises.

Then Jackie moved into her own apartment. We would still get together and exercise but we also would just have sex. I know there were unconventional things about Jackie. Since our relationship wasn't exclusive, we saw others. Jackie would ask me about the others and one day informed me she liked the way my cock tasted after sex with certain women and would I bring them around to introduce them to Jackie. My curiosity made me ask if she was interested in them sexually. She just laughed and told me, " With girls things are different, not every kiss is platonic."

And then she said "Women sometimes slip back and forth".

So when the day came she introduced her vibrator into our sexual activities I was open minded. We were laying in bed clothed, she was wearing a skirt. We began kissing progressively getting hotter. I unbuttoned her blouse and she removed it along with her bra. I kissed softly slowly moving toward her breasts squeezing softly and teasing the nipples. I kissed along her neck until i reached her chest and then to her breast. She tasted a little salty and lemony as she used something with lemon juice. I loved the way she tasted as I licked around the nipple flicking my tongue over the nipple before taking it in my mouth.

As I sucked gently I continued to tease the nipple with my tongue which made her squirm a little. I continued to caress the breast not in my mouth, rolling the nipple between my thumb and finger. Jackie undid my pants and began pushing them down. I was sucking first one then the other slowly giving equal time as i sucked deeply and slowly pulling her breast from my mouth. Jackie put her feet on my pants and tried to push them off. I had to stop what I was doing to remove them.

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When I came up a towel replaced the pillow across the top of the bed. I went back to Jackie's breasts and she wrapped her fingers around my cock stroking and pulling on it. She continued squirming and humming, and vocalizing. Then she said, I've been wanting to suck you all day. Then she produced the vibrator. She turned it on low and said, "First I need to get you ready".

She applied the vibrator to the base of my shaft at the balls. Now it was my time to squirm.The vibrator felt interesting where she placed it. The vibrations seem to carry all the way up to the tip. She asked if I had a favorite place. I told her I had not done this before. She moved it between my legs and said I was in for a treat. She bent down and sucked my cock into her mouth. The feeling of her warm wet mouth was just what my cock wanted and I couldn't help but raise my hips to put it deeper. She cupped my balls as she sucked and rubbed my perineum with her fingers. She replaced her fingers with the vibrator. As she pressed the vibrator hummed against me it felt so good I pressed back against it. She sucked me deep int her mouth and pressed the vibrator against my anus. I didn't know how good massaging my anus would feel.

As She bobbed up and down on my cock she worked the vibrator back and forth between my legs pressing it into my anus. Slowly she started to push the vibrator into me. I wanted to push down on it.Then she lowered the vibrator and I felt a wetness in the area. As she applied the cool wet cream she pushed a finger slowly into my ass. It resisted at first, but she applied more until her fingers slid in easily. I was about to ask what she was doing and the vibrator returned lubed this time. She pressed the vibrator into my ass slowly.

I was distracted for a while but as the vibrator slipped deeper it began to feel good. I relaxed and let her probe me working her vibrator in and out as she sucked. I soon found myself moving with her as she pushed it in and out. I began to feel things building deep inside my balls. She seemed to sense it too as she pushed the vibrator deep, she had me sit up. I was sitting on the vibrator pushing it deep inside my ass. I exploded filling Jackie's mouth with cum, she caught every bit. When I was finished squirting she climbed onto my lap inserted my softening cock into her pussy. As it slipped inside her, she put the lip lock on me grabbing my head, holding it tightly in place. She tried opening my mouth with hers.

As it began to open she shared her prize with me. Jackie inserted her tongue as my mouth filled with cum she rubbed my tongue with hers. This brought my cock back to life surprisingly quick. We went for round two. It was an interesting feeling, having a vibrator which she had turned to high as she sat me up, and her bouncing up and down on my cock. it wasn't long until she began squealing as she came and I came right with her. We settled as our climaxes subsided. She said she would have to do this more often as sex was better with a vibrator up my ass. She was sure she could feel the vibrations transmitted through me somehow. This became a semi-regular thing for us. Later she bought a vibrator made of rubber and shaped like a penis. It felt much better though not like a real penis.

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