tagMatureUnexpected Encounter

Unexpected Encounter

byjackstraw2©

**I have been reading stories on this site for several years but this is the first time I have ever written one. The stories that turn me on the most are the ones that are true, or at least written as true. I decided that if I were going to write one I would only write about my real experiences. So what follows is my first account of something that happened to me about 5 years ago when I was living in Florida. The only thing that has been changed about this story are the names.

I moved to Florida for a new job in 2001. I was 27. The town I was living in was a small town and there weren't many young single people. After awhile I was getting pretty sexually frustrated and had resorted to more jerking off than I ever had before. I'm a pretty good looking guy, about 6' tall, 170 lbs with brown hair and bedroom blue eyes.

I had moved into one of those master planned communities, you know where all the houses look exactly the same and are lined up like sardines. Most of my neighbors were older retired people and I knew most of them but didn't socialize with them beyond a wave if I saw them.

One day after about a year living there, there was a knock on my door around 6pm, after I had gotten home from work. I opened it to find Cheryl, a neighbor of mine that I had met several times when I had been out jogging. She looked somewhat distraught. She asked if my father was around. My parents had come to visit me twice during the previous year and Cheryl had met them several times and gone to dinner with them one night with her husband.

I was a bit puzzled by her question and told her that no, they were back in Connecticut. "Oh", she said with a disappointed look.

"Is something wrong?" I asked. Bad question. She immediately starting rambling about her husband who had died a month before (I had not known). Then she said that her only son, who lived in Tampa with his new wife and baby, had been mugged and murdered the previous week. I was shocked to say the least. As I said, I didn't interact with my neighbors much so I knew none of this. By the time she got through what she had been through over the last month, losing her husband and only son, she was crying.

I felt bad standing there in the doorway, with her outside in the 90 degree heat so I put my arm around her shoulder and guided her inside. Apparently, she wanted to talk to my father, who was a lawyer, about the various estate matters that she was now faced with and that were just too difficult for her to deal with in her current emotional state.

Now, before I go any further, I have to say that I hadn't intended anything sexual when I invited her in. Cheryl is not an ugly woman. She had just turned 50 and had aged well. She had dirty blond hair, shoulder length, and was about 5'4". She was a bit over-weight, maybe 150 lbs, but wore it very well. Which is to say, she has VERY large breasts. I had noticed that when I met her months before. Regardless of what she wore, they were difficult to hide. I guessed her bra size must have been 38 DD or maybe even E. she was actually one of the younger women in the development.

Being from the northeast, the Florida heat was a killer for me and I always had the AC on very high. My home felt like an ice-box and I offered Cheryl a drink. She accepted a glass of white wine. She was wearing a pair of white shorts and a green v-neck t-shirt against which her ample breasts were beautifully framed. The AC had made her nipples hard and they showed through the shirt nicely. As we sat in the living room I began to get more and more distracted by those glorious tits as she rambled on about her son and what her daughter-in-law and grand-daughter were going to do now that he was gone.

I know this sounds horrible so far but I hope you read the rest to know that I'm not a bad guy.

Anyway, she started sobbing again and I moved from my chair across from her to sit beside her on the sofa. I sat on her right and put my left arm around her shoulders and she immediately turned and leaned her head against my shoulder. I put my right hand around her back and my forearm was resting against her massive left breast.

She cried harder for a few minutes and I tried to comfort her, telling her everything would be alright. I had begun rubbing her back with my right hand, the whole time my forearm sliding up and down her breast. She didn't seem to notice that or care if she did. This was driving me crazy as I hadn't been laid in months. My cock was getting hard thinking about her beautiful tits and I decided I had nothing to lose.

I let my right hand gradually move from rubbing her back to rubbing the side of her rib cage. I gradually let my thumb slide closer and closer to the side of her breast until it was firmly stroking the side of her large mound. She made no protest, and her sobs grew less pronounced. I was nervous. I didn't know how she would react to what I was doing.

Her arms got a bit tighter around my neck and I took this as a sign that she liked what I was doing so I moved my hand to cup her breast completely. She was a little startled by that and she started to lift her head off my shoulder, but I just said to myself, "fuck it" and kissed her lips. I pressed my tongue between her lips and she reluctantly opened her mouth.

We sat on the couch making out like high school kids, my right hand glued to her left breast. I eventually slid my hand under her shirt to get one layer closer to her amazing mounds of flesh. She didn't say anything and neither did I. But I wanted to take her bra off and she knew it. I didn't quite know how I should go about this. It's hard to get a woman's bra off while you're sitting on a couch.

So I quickly removed my hands from her body and ripped my shirt off. She smiled a little at me, the tears still drying on her face. I stood up and grabbed her hand and pulled her up as well. She immediately started kissing my chest and as much as I wanted to get her shirt and bra off I let her do this for a few minutes. I was pretty damn hard now and my dick was making a tent in my shorts. This was pressing into her hip pretty strongly.

I leaned down to kiss her neck and spent a minute or two doing this before spinning her around and cupping both of her breasts in my hands pretty roughly. I massaged them through her t-shirt and as I did this, she started pushing her ass back into my cock. I quickly slid my hands down to the tail of the t-shirt and lifted it up to her neck. She raised her arms in quiet consent and the shirt was finally on the floor.

I love looking at a woman's tits in a bra and as we stood in the living room I could see our reflection in the window which acted like a mirror since it was now dark outside. I continued to kiss her neck, with my eyes open, mainly so I could watch her cleavage as I played enthusiastically with her gorgeous tits. She was wearing a white bra, open across the tops of her breasts and they were just as awesome as I could have imagined. She kept pushing her ass back on my dick and I obliged by pressing back into her and we stood like that, swaying back and forth, dry fucking if you will for a good 10 minutes.

By this time, my dick was raging. She had kept her hands on my hips occasionally moving them over my ass during this time. Before I went for the bra I wanted to give her something as a distraction. So I quickly removed my hands from those massive tits and undid my shorts, sliding them and my boxers off my hips. My cock sprang free and because she was so tentative I took her left hand and immediately moved it to my cock, where she promptly began stroking me. It didn't take long for pre-cum to begin oozing out of me. I turned her face toward me and buried my tongue in her mouth, and she eagerly kissed me back.

Now it was time. I moved my hands to the clasp of her bra and began working on it. Because her tits were so big and heavy she was wearing a bra with 3 hooks. The first one was the easiest to undo and they were harder to get after that. That last hook might have come off on its own. The damn thing was probably holding 10 pounds worth of tit flesh by itself! I felt her tits sag as the last one came undone and I slid the straps off her shoulders.

Usually I'm pretty gentle with a woman's tits, but because it had been so long since I'd been laid and because I sensed how vulnerable this woman was and how I needed to be aggressive, lest she change her mind about this very taboo thing that we were doing, I felt I should let her know I was in control. So I kneaded those beauties between my hands like there was no tomorrow. Her nipples were extended and I could tell she'd breast fed her kids. Her areola were enormous, maybe 4 inches across and I was salivating over the prospect of nursing on them. All the while I played my tongue around her mouth, my eyes open the whole time to watch her glorious breasts roll beneath my fingers.

Every once in awhile I caught our reflection in the window and smiled at myself. What can I say? This was pretty hot. The arousal was building and I knew that I was going to cum eventually so I had a choice. Should I sit her down on the couch and try and get her to suck me off or should I go for the whole sha-bang? I hadn't made a move for her pussy and didn't know how she'd react. Although at this point, it seemed she was pretty willing to let me call the shots.

I made my decision and grabbed her hand and pulled her to the bedroom. She hadn't said a word this whole time and I hadn't either. Usually I like to talk a little during sex. Anyway, when we got to the bedroom I started kissing her aggressively face to face now. Her breasts were mashed against my chest and they felt great. I ran my hands over her ass, clad in those loose-fitting summer shorts. I squeezed her ample butt cheeks which made her gasp again, and then moved my hands to the front and undid the button. I dropped to my knees pulling her shorts and panties with me as I went.

I was thrilled to find her pussy both shaved and wet. I picked her leg up and put it over my shoulder while I went to work lapping at her clit. This drove her crazy and for the first time since we had gotten it on, she started talking. "oh my God" she said over and over. I suspected she hadn't been touched in a long time. I loved looking up at her tits while I licked her pussy; they looked just as good from underneath, lol. After a minute she took one of her hands and began playing with her nipple. She didn't last long, and squirted her first orgasm on my face. I lapped it up and stood up and kissed her hard, forcing her to lick her juices off my face.

I pushed her back on the bed and held her legs up and knelt between them. Missionary isn't my favorite position but I wanted to watch her tits bounce around while I fucked her. My cock sticks straight up and so I pointed the shaft down and rubbed the head up and down her slit for a minute, coating my cock with her juices. I like pentetrating a woman right after she cums. Her puss is soaking wet and makes a great smacking sound while you thrust. I pushed the head past her labia and leaned over her to get myself fully into her. I'm only about 6 ½ inches but because my dick sticks straight up, it was straining pretty hard against her clit from the position I'd entered her.

I started thrusting, pretty slow at first, sliding my hands up and down her flanks. A few times, when I felt myself getting close to cumming I stopped pumping her and leaned down to suckle one of those gorgeous nipples. Then I got back up and started pumping her again. I used my thumb to rub her clit, which she clearly loved. I felt her cum again and she squirted over my stomach and onto hers. This really turned me on and I decided it was time to end the torture for myself.

I let go of her legs and lay down on top of her to get my full weight into each thrust. Like I said, I love fucking a pussy right after orgasm and she'd had two, so she was absolutely soaked. I positioned myself as high up on her hips as possible, immersing my full length in her and began to thrust. She had her feet flat on the bed and I wanted her to rotate her hips a little more so I told her to wrap her legs around my back. She complied immediately and this really opened her up to my thrusts. As I said, she had a pretty plump ass so I was really able to drive her pussy with force. The feeling was amazing. Her pussy was loose and soaked and her walls were massaging my shaft like crazy. our bodies made a "smacking" and "juicing" sound every time I thrusted, because our stomachs & genitals were so wet.

I felt that familiar heat building in my balls and quickened my pace. I lay my chest firmly against hers and slid my left hand under her right ass cheek to gain a bit more leverage for my thrusts and entered the home stretch. I couldn't take it any more and cried out, "Oh God, I'm cumming!" Lame, maybe. But I wanted her to know it. "oh my God," she said as she felt my heat rush into her. 5, 10 good bursts of semen filled her hungry cunt as I ground the base of my shaft against her labia, which were squeezing me back, milking every drop from me.

I collapsed on top of her and she stroked my back while my cock settled down. We lay like that for a good 3-4 minutes, her massive breasts keeping me from going completely limp.

The night wasn't over...

***My relationship with Cheryl continued for many months and got far more adventurous. However, if readers feel as though I took advantage of this woman, then I won't continue to write. I think we both look back on that period of time with great fondness and I think we both really needed what the other provided. Responses are welcome. This is the first time I have ever written anything.

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byjackstraw2© 20 comments/ 143827 views/ 1 favorites

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