Category: older younger

Babysitter Stripper

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It took a long time to find a babysitter for my infant child, but when my wife called one day to say she had found the perfect girl, I was thrilled that we’d finally be able to go out once again. My wife was beautiful, she had nice D cup breasts and a delicious body, but our sex life had been sapped by the arrival of a baby. At 25 we were both overwhelmed by the responsibilities of children and careers and we hadn’t had much time for each other.

Our first date in a year occurred a week later when we went out to a movie and dinner. The babysitter was a stunningly beautiful 18 year old named Victoria, who was getting ready to attend college the next year. Victoria was every man’s fantasy, a chirpy, big –breasted, thin girl with a gorgeous face and long, Italian brunette hair. The first time I saw her I nearly had an instant erection. My wife had found her through a co-worker, apparently she was an in-demand babysitter, and at least from my perspective, I could see why. She arrived in a short black skirt and a low cut top, and after making arrangements with my wife we both left her to sit with the kid. At the movie and dinner I enjoyed my alone time with my wife, but Victoria stayed in my mind. That night, my wife drove Victoria home, and I jerked off while she was gone.(to my disappointment). When my wife got home I threw her into bed and make passionate love to her, but again Victoria was nagging me with thoughts of her sumptuous body.

Over the next several months Victoria babysat for us about every two weeks, and the routine continued. I gradually got to know her through our short, two minute encounters. One night, my wife drank too much wine and asked me to take Victoria home instead. I obliged, and realizing I needed to write Victoria a check for her work, I quickly sat down at the kitchen table and opened the checkbook. As I was writing Victoria walked by, accidentally dropping some of her makeup on the floor. I couldn’t help but stare as she bent over to pick it up, giving me a view to die for. Her pleated skirt was just the right length, rising just high enough to give me a peak of a sexy black thong. I had an instant hard-on, and suddenly she caught my gaze and blushed. I continued writing, but we both knew that I had been looking and enjoying the view.

I drove her home after her little bending over incident, but she seemed extra interested in me in a way that she hadn’t happened before. She laughed at my mini-jokes that weren’t funny, she smiled at me, and I swear that she pressed those sexy breasts together just to give me a view as she sat in the passenger seat. In the weeks that followed the flirting continued, I even caught one glare from my wife, but I figured it was just playful fun. About eight weeks after my gaze, I drove Victoria home again. This time Victoria started asking about the health of my marriage and my sex life. I told her that I loved my wife, but our sex life was a bit boring. She said that was too bad, and then she told me about her sex life. Apparently she had a boyfriend who had gotten pretty serious, and the implicit message was that she wasn’t a virgin. They had a hard breakup three months back, and now Victoria was out on the prowl, looking for a decent man. She finished her story as we pulled up to her house, and I said “Ok, See ya next time.” As she got out, she smiled, her red bra was visible all the way around her low cut tank top, and she climbed out of the car. This time though, she gave me a deliberate view of her red panties. They were see through boy shorts that hugged her beautiful ass, and I nearly burst in my pants. We smiled at each other as she walked away; I rushed home to masturbate and fuck my wife.
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Thigh Highs

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Funny how you have flash-backs at strange times. I was trying to recover from an incredibly hot orgasm and all I could think of was more! more!

My panties were gone, my legs were sweaty and trembling, but I was insatiable. This night was far from over that much was sure.

As I sat and contemplated my next move, my mind drifted back to my high school days. It was just after my 18th birthday and my mom had arranged for me to babysit for the couple next door. I didn’t mind at all, I actually liked Rob and Sharon. I even liked their kids. But I especially liked Rob.

Rob and Sharon were in their early thirties, well built, both worked out all the time. I must admit I used to fantasize about Rob. I dreamed of him taking me by force, holding me down, ripping my panties away and having his way with me. I often watched him do yard work, hoping he would shed his shirt just to get a glimpse of his mountainous chest.

I guess I felt such fantasy was safe because I knew it would never happen. It was just a school girl crush, but it was still enjoyable. It made me wet and horny enough to get me through many a lonely night of fingering myself into fantastic release.

This day would be no different. I was to drive over to their house after church on Sunday, watch the kids for a few hours while they went to some social thing. No big deal.

Maybe subconsciously that was the reason I dressed the way I did, I’ll never know. It was just fun to dress up when Rob was around. When I was alone in their house I would sometimes pretend he was married to me… imagining all the things I would do to that body when he got home from work… all the places his tongue would explore as he tasted every inch of my young, tanned, submissive body.

I remember, because it was the first time I ever wore thigh highs. Smooth, silky, cream-colored thigh highs with that sexy, lacy, rubbery grip top. They felt so erotic when I put them on… and the matching creamy lace thong was just perfect. Just looking at them in the mirror made me want to play with myself, but I had no time for that. Still, I felt so sexy in church I just kept crossing and uncrossing my legs so I could hear that delicious swishing sound.

I could feel the eyes of all the young guys staring at me, even the married ones. Once I even thought I caught the minister trying to get a glimpse up my dress, and that just made it worse. It only served to fan the voyeuristic fire that was burning deep within my panties.

Finally the service was over and I headed over to meet up with the kids. When I got there, Rob emerged from the bedroom in a short muscle shirt and skin-tight work-out pants. He said Sharon had been at her mother’s house for the weekend, and would be a couple of hours late.

I started to go home, but he said to hang out there and wait, no sense making another trip. His deep voice made my heart skip, he was so insistent that I stay. My fantasy began to take shape again, there we were, the perfect little married couple, home alone on Sunday afternoon.
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Birthday Bang

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It was a boring evening. All I was doing was stare at the television in a blue funk. The Mets were losing; crime was up, and much like my love life, the stock market sucked. Nothing new or exciting. And then the telephone rang.

I answered it to a woman on the other end. “Hello,” she said, “This is Mary. Is Kevin there?”

How nice! I thought, a sweet sexy sounding woman’s voice to talk to. But she was asking for another guy.

“Sorry, ma’am,” I answered, “but you’ve got the wrong number.” I hung up. But that voice stayed on my mind and I wondered what she looked like.

Minutes later the phone rang again. When I answered it I was surprised and pleased to hear her voice again. She asked the same question. Only this time, I thought I would be a bit flirtatious, and see what happened.

“No, Mary…. Kevin isn’t here but if you don’t mind my saying, I truly love your voice and I’d love to entertain you even though I’m not Kevin.”

She laughed at my response and asked my name.

“I’m Roger. But you can Rog.”

She giggled a little and said, “Well, Rog. Your voice sounds pretty sexy.”

We ended up talking for hours that evening. We learned a lot about each other. Mary told me that she was a 39- year-old office assistant and part-time personal trainer at a gym franchise. She explained that she just had her divorce of 5 years finalized and that she was looking for her friend, Kevin, to spend a few hours with to relieve her of her misery.

However, our telephone conversation managed to do the trick. I kept Mary laughing and in a good mood. That one evening turned into a daily, 2-hour telephone conversation between Mary and I.

Two weeks after our first conversation, Mary called feeling depressed because it was her birthday and she didn’t have her husband or friend to spend it with. I suggested to her that I would be happy to take her out for her birthday. But she said, “Rog, I am a bit older than you baby. I doubt that we would have anything in common.”

I am 25 and work as a department store manager. I explained to her, “But Mary, this doesn’t have to be a romantic thing if you don’t want. This is a simple Happy Birthday ‘get together’ to bring in your 40th birthday.”

She was somehow convinced so we agreed to meet at a public location and celebrate her birthday. But I had a great surprise for her.
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Nice Day At Work

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The rain had started and business was slowing down as we headed into our off-season. I was scribbling notes in the personnel file, trying to figure out how to avoid big staff cuts through the winter. I knew some hours had to be slashed, but I always hated doing it. I must have looked to be in a sour mood, because the whole staff avoided contact with me other than the routine hellos and brief exchanges needed to run things. I rolled my chair away from the desk, trying to unjam my brain, and looked out the window at the will call counter

She had worked for us for 4 summers – ever since her junior year of high school. She was a cute kid then, but was just now starting to lose that teen baby face. In its place, she was beginning to take on the look of a strikingly beautiful woman. She let her auburn hair grow a little longer than usual this year, just a few inches past her shoulders, and when she was close by I could smell the lightly sweet fragrance of that soft hair every time she brushed it with her fingers or turned her head. Despite my strict rule against personal relationships with anyone at work, I had quite a crush on her. I was cautious to be professional in her presence trying to avoid being obvious, or create the impression that she was given any preferential treatment.

I never thought she would stay with us for so long, but I was glad she did. She was smart, friendly and customers liked her. She had just returned from a trip to Vegas with her fiance for her belated 21st birthday and I found myself taking more and more chances sneaking glances at her gorgeous body. Being a fan of a curvy backside, she was a constant reminder of what a perfect womanly ass looks like. I recalled pieces of a conversation I overheard between her and another female co-worker as they shared stories of what their respective boyfriends did (and didn’t) do for them sexually. My mind drifted back to it lazily.

“Great!”, I thought to myself, “On top of everything else – now I’m horny as hell.” I gathered myself and made my way back to the desk. If there wasn’t the sound of people talking in the break room and hallway nearby, I probably would have locked my door and given myself a quick jerk to relieve the tension. I cursed my own open-door policy and tried to get back to the pile of to-dos on the desk. It took awhile, but I got back into my work groove and managed to be productive the rest of the afternoon.

I hadn’t looked at the clock for quite some time – apparently a few hours – and was surprised to hear myself saying my daily “goodbyes” to the night staff as they left. I leaned back in my chair, closed my eyes and stretched my arms over my head when I caught a familiar scent.

“Boss?” said a low voice, startling me from my stretch. I looked over to the doorway and she was standing there leaned against the jamb with her hands in front of her – twisting and fiddling with her fingers nervously. “Can I talk to you a sec?”
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The Masseur

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Jason worked as a masseur. Even after all this time, he still enjoyed the relaxed atmosphere of the spa, the soft music, the aroma of incense and oils. Most of all, he enjoyed the pleasure his touch could bring to another. He’d learned to play piano as a child and the act of touching another person’s body with his strong, nimble hands reminded him of playing a challenging piece. You played with a gentle touch here, a little pressure there, until your client became your instrument and her sighs and moans your symphony

Jason especially looked forward to Wednesday mornings. That was when Alexis Carter sought relief from muscles strained during her hard fought tennis matches. Tan and supple, he guessed her to be in her early thirties. She was a tall, dark haired beauty with high flaring cheek bones, wide-set brown eyes and long, muscular limbs. A self-assured and well-known real estate agent, she was divorced and had a reputation for running with a fast crowd.

Jason was standing at the counter when Alexis pulled up in her BMW convertible. He watched as she exited the car and strode across the parking lot. She wore a hot pink top and matching skirt that ended several inches above her knees. When she bent over to tie her shoe, Jason waited for the glint of pink panties underneath. Yes, there it was.

“He-ey,” Alexis sang out, stretching the word into two syllables. “It’s my favorite masseur.” Although she gave Jason her usual brilliant smile and peck on the cheek, her carefree demeanor seemed to mask some inner turmoil this morning. Perhaps the tone of her voice was a little flat, her kiss somewhat perfunctory. It was hard to say.

“Hi there,” Jason beamed in return. “Come on in.”

Jason had acquired Alexis as a referral from another client, Leslie, a compact blonde that reminded him of the high school cheerleaders he’d lusted after in high school. She and Alexis had met and become friends in an aerobics class while Alexis was going through her divorce.

“You’ve got to do this,” Leslie had gushed to Alexis at a neighborhood barbecue. “This man has the most amazing hands.”

Alexis had smiled wickedly. “Well, I look forward to finding out.”
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On The Road Again

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It’s a long straight stretch of road; not another car in either direction for quite some time. With my lady asleep in the back seat its hard to stay awake as we make our way into upper Canada. I was surprised she agreed to go fishing with me, but the load of books she brought along pretty much explained her plans.

I rounded a corner and almost hit the kid on the shoulder. I swerved away from him and hit the brakes. He ran up alongside the car and I rolled down the window. “Sorry, man,” I said,” I didn’t see you around the curve.”

“No problem,” he grinned, “You missed me. How about a lift?”

He seemed safe enough, maybe early twenties, a bit smaller than me. I could use the conversation I thought, and popped the lock on the door. He climbed in, buckled up and we were back on the road.

He had noticed my girl in the back, so we kept our voices low. He turned out to be from near the area I was headed to, hitching home from college for a few weeks. We talked about where the locals fished, places the motel owner probably wouldn’t send me to. As we drove my lady slept soundly, spred out on the seat.

I noticed he was having a hard time not looking in the back as we talked. I adjusted the mirror and saw what had caught his eye. Her blouse had come unbuttoned and her breast was completely exposed.
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The School Reunion

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Scott Ruden drummed his fingers on the leather covered steering wheel, keeping time with the beat coming from car radio. His thoughts, however, were not on the music, but his twentieth high school reunion being held that weekend in his home town. He had been pretty lucky over the years and had done quite well with his computer soft ware company, so at least he wasn’t going to have to make up a lot of stories about how his life has been going. It had been at least fifteen years since he had been to Maplewood, the last time being to bury his mother, so he really had had given no thought of coming back until he received his invitation in the mail. It was a five hundred mile drive, and it felt good to escape the big city tension for the pastoral calm of the green country side. About an hour later, Scott could make out the water tower that had maple leaves painted all over it. “Still looks just as hokey as ever,” he thought, as he turned down main street, marveling at how little change had taken place in all those years. Patterson’s Men’s Clothing was still on the corner, and Jenkins’ Drug Store still had the same old pink neon sign that had been there since he was a boy growing up. The memories flooded back with each old store, house, or park that came into view. He took a right on Elm Street, and two blocks later he slowed down and drove by the old homestead. Shutters had been added to the front windows, and the once white paint job was now an earth tone tan, but to Scott it still was home. He glanced at his watch and realized that the reception was already started, so he gunned the motor and headed off to the high school.
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My Husband is Away

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I am sorry babe, but I have really tried to be good while you have been away, but I want to be honest with you, so feel that I should tell you about what happened today.You know I told you that they came to do the gas inspection today, well what I did not tell you was that when the door went I opened it to two men. Well when I say two men, there was a bloke who looked to be in his thirties and a young lad, who I was told had just left school and was on an apprentership. The older one said that if it was o.k with me that he would leave the lad to do the inspection and when he had fininshed that he was to call him, and he would then come back to check on his work.

I said that was fine and then he left, leaving me with this gorgeous young lad!I am sorry babe, but I could not help myself from watching him and thinking what I would like to do to him. I got chatting to him and he said he was eighteen and lived locally. He was so cute and it looked like he had a really nice body and I found myself feeling so horny and decided that this was going to be my first taste of young cock. So, while he had his back to me busy taking the fire apart I started to play with my tits, rubbing my nipples until they were rock hard and I could feel my pussy getting wet. I was enjoying it so much that I had not noticed him turn around and that he was watching me open mouthed. At first he looked embarrassed, after all I was not far off old enought to be his mum but it was getting me so wet seeing the bulge in his jeans that I asked him if he would like to come and sit on the sofa.
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Smooth Teen Pussy

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Samantha sat on the edge of the tub with her legs spread wide apart while she very carefully maneuvered the safety razor along her bulging vaginal lips, using tiny short strokes to remove the final remnants of hair from her eighteen year old pussy. A knock on the bathroom door made her pause as she asked who it was. “Just me,” shouted her best friend Priscilla through the closed door, “can I come in?!?” “Sure, Pris, come on in, I’m almost finished here anyway,” intoned Samantha as she went back to her barbering!

Priscilla nearly burst through the door and took a seat on the closed toilet lid and asked, “What in the hell are you doing, Sam, it looks like your taking it all off!?!” Continuing with her shaving, Samantha replied, “That’s right, babe, I’m getting rid of all of it, with summer coming up, I want a nice clean look for my new bikini.” Priscilla didn’t answer for awhile, but watched intently as her friend scraped away her remaining pubes. “Doesn’t it sting,” she finally asked, “it looks like it burns like the dickens.” “Not too badly,” Sam replied, “and I’m going to rub it with baby oil when I’m finished, that should take away the sting!” Pris looked doubtful, but held her tongue as Samantha wiped away the excess lather and dabbed away the remaining moisture with a fluffy towel.

“Well,” asked Samantha, “how does it look!?!” “Like a five year old,” Pris retorted quickly, “but I have to admit that it does look sexy in an odd sort of way, how does it feel?” “Mmmmm, very erotic, the air is really cool on it,” Sam replied softly, “look at my clit, it’s all puffed up.” Priscilla leaned forward for a better look, and was astounded at what she saw. There at the top of Sam’s crack, poked out the head of her very erect clitoris. “My god, Sam,” she moaned quietly, “you must be on fire.” Sam’s breathing was now becoming labored, and along the length of crack moisture appeared in small droplets, looking for all the world like a string of small pearls! Without asking, Priscilla picked up the baby oil, turned on the hot water and held the bottle under the faucet for a minute or so to warm up its contents, and then squeezed a generous squirt into her hand, where upon she rubbed the warm oil gently into Samantha’s freshly shaven mound.
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Meeting An Old Friend

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I always did like a good fucking – just the way I am, I guess. Nothing like good dick in my pussy to make me happy. I was thinking that that day while I walked.

I was in the supermarket of the town I grew up in when I heard a voice behind me. It said “Jenny! Jenny Shores is that you?” I looked behind me and it was Mr. Jones the neighbor that lived across the road from us when I was growing up!

I hadn’t seen him in years but he still looked good, he was beginning to go grey around the temples but mixed with his afro carribbean features it suited him. His family was nice. I had many happy memories of hanging out in their house and playing with there kids. He was the first black man I had ever met and I remember having sexual thoughts about him in my early teens but I don’t think he ever regarded me as anything more than a kid. It was different now though. His eyes were all over me staring at me hungrily, and he said “Look at you! you’re all grown up, it seems like only yesterday you where running around in your underwear and sucking on a licorice stick!” I said “well I still like to suck on licorice sticks especially the big fat ones and if you want to see me running around in my underwear I’m sure it can be arranged…”
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