I couldn’t get Jennifer out of my mind. Cute, friendly, attractive, out-going, sexually deprived and aggressive, I knew I was in trouble once I laid eyes on her. Twenty years old and a true fox! Her dad worked across the hall from my office, in a small multi-tenant office building. Every now and then, Jennifer would stop by to chat with her dad, to let him know she would be with her friends, hanging out nearby. Our offices were close to a small entertainment district – mostly bars and restaurants. On nights when I would work late, it became a habit for me to stroll down the sidewalk, after work, past Jennifer and her friends as they sat and chatted. Sometimes, a silence fell on the group as I walked by, and sometimes I could hear their girlish giggles. I never really gave much attention to the group. Jennifer was my primary focus.
Taking Jennifer home became a habit. She knew I had a strong attraction for her and she seemed to enjoy teasing me, either by giving me a wink, or saying something so overtly provocative, that I couldn’t ignore it. I did my best to keep our time to together, very innocuous and non-sexual, but Jennifer just couldn’t resist being the tease.
One evening, as I was taking Jennifer home, she told me that one of her friends had a crush on me. I laughed.
“I’m serious,” Jennifer shot back. “She’d thinks you’re hot!”
I’m pretty sure I blushed a little, but I brushed off her comment.
“I’m serious,” Jennifer responded. “You’re a good looking guy, so you should just say, ‘thanks’.”
I ignored her response, which in hindsight, seemed to set off a chain reaction discussion.
“You think because I’m twenty, I don’t know a good thing when I see it?” Jennifer pressed.
I was old enough to be Jennifer’s dad. I reminded her of that fact, but it did not seem to matter to Jennifer.
“I like older guys,” Jennifer responded, flipping her hair back over her shoulder. “Guys my age are so immature.”
Then, all of the wild blue, Jennifer asked, “So what is your sexual fantasy?”
I reminded Jennifer that I was married.
“You can still have fantasies,” she replied. I stayed quiet for a second, not sure of how to respond and if should.
“It involves a lot of debauchery,” I replied. Jennifer stayed silent for a moment, staring out the window.
“I like debauchery,” she finally said, adding, “I have no clue what it means, but it sounds dirty and fun.”
I had to chuckle. Her innocence was so beguiling.
As we drove down one of the main streets not far from her house, she twirled a long finger in her long hair. I could tell she was kind of lost in her own thought and perhaps, a bit apprehensive. Then, out the the blue, once again, she announced,
“I was thinking about becoming a stripper. Do you think guys would find me attractive?”
I had to shift in my seat a little to relieve the pressure that had began to form in my pants.
“Yes,” I replied. I was floored. I knew that Jennifer probably had a wild side, but never expected her to be the type that would know anything about the world of stripping.
“Really?” I quizzically replied. “Why would you want to be a stripper?”
“I don’t know,” she innocently replied. “I hear the money is good, and I could use some money.”
I did my best to reassure her that while the money might sound alluring, that stripping was a hard life and one fraught with many perils, such as drugs and prostitution, which lead to a whole other discussion.
“I don’t see any problem in getting paid to have sex,” Jennifer disclosed.
I was stunned.
“Have you ever had sex with someone for money?” I asked.
“Not yet,” Jennifer replied.
“But you would?” I asked.
“Depends on how much a guy would be willing to pay,” Jennifer replied. “What do you think I am worth?”
“I don’t know,” I replied. “I’m not looking to pay for sex.”
“Would you pay to see me strip?” she asked.
“Maybe,” I replied.
“You would?” she shot back. “Really?”
“Yeah,” I replied. “Why not? I mean, you’re a good looking girl, and if you wanted to hump up and down on my lap, I wouldn’t say ‘no’.”
Dirty, lascivious thoughts raced through my mind, but this was much different. I had been in strip clubs before, but this was different. I knew Jennifer on a while different level.
“It would have to be our secret,” Jennifer replied.
“You know,” I said, “If your dad finds out, he will kill us both, bury us, dig us up and kill us again.”
Jennifer chuckled.
“Yeah, he would be like that.”
I drove past Jennifer’s house and stopped a couple of doors down from the usual drop off.
Jennifer opened the door to my SUV and smiled. I watched as she trotted up the sidewalk to her front porch, opened the front door and disappeared.
The next day, I couldn’t get what Jennifer had confided in me. I was working hard trying to meet some deadlines, when Jason, Jennifer’s clueless dad, stuck his head in my office.
“I’m off to south Texas for a few days,” Jason announced.
“Cool,” I replied.
“I told Jennifer that if she needed a ride, to hit you up, if that is okay,” Jason said. “I really appreciate you being there to help out when she needs a ride.”
Damn, now I felt guilty.
I refocused on my work. About an hour later and I heard a light tapping on my door. I looked up and saw Jennifer standing in the doorway sporting cut-offs that were a little immodest and a tight fitting light blue college t-shirt with a backpack slung over her shoulder.
“Hey you,” she called out, “Can I get a ride home?”
I was more than willing. As we tooled along towards her house, I tried my best to keep my eyes focused on the road and my driving. I didn’t dare bring up the subject from the previous night.
“Do you have some spare time,” Jennifer non-chalantly inquired. I told her that I did.
When she didn’t say anything else, I asked, “Why?”
“I’d like to try out for you,” she said.
“Try out?” I asked, having momentarily forgotten our previous conversation. “”For what?”
“You know,” she replied, “Our little secret.”
Damn.
“Okay,” I replied, “But when and were?”
“Dad’s gone and mom won’t be home from work for several hours,” she replied.
My mind was racing. I asked of she was sure and she said she was one hundred per cent sure as I pulled up in front of her house.
“You don’t mind if I call a friend, do you?” she asked as I followed her into her house.
“Go for it,” I replied.
I settled on to an oversized leather couch in the middle of the modestly decorated family room. Jennifer turned on the house stereo, rap music blaring from the speakers.
She dialed a number on her cell phone, and then smiled at me as she flipped her long hair over her shoulders. I heard her say into the phone, “Come on over.”
She tossed the phone on to a nearby table. She shifted her shoulders and head back and forth to the beat of the music. She slowly worked her way over to where I was seated on the couch, biting down on her lower lip, her hips swaying back and forth to the ‘thump-thump-thump’ of the music.
She tapped the inside of my ankle and I instinctively spread my legs as she stepped between them, facing me. The inside portion of the pockets to her cut-offs hung past the frayed edges of her shorts. The lower half of her butt-check was clearly evident from the back. Her bare well-tanned and toned legs rubbed up against the inside of my thighs as she looked down at me.
“What do you think?,” she asked, shouting over the music.
“I think you look great!” I replied.
She turned, placing her buttocks in my face and very suggestively lowered herself on to my lap while steadying herself by placing her hands on my thighs.
“So far, so good?” she asked looking back over her shoulder at me.
“Oh yes!” I replied, lightly patting her hip. “Very good!”
I let my hand stay in place, just to see what if any reaction it might elicit. She placed her hand on top of mine and smiled. I slipped my hand down to her bare leg and tried to insert my finger tips under the edge of her skin-tight cut-offs.
There was a loud knock on the front door. Jennifer quickly moved to open it.
This was my introduction to Monica.
If Jennifer had a twin, Monica could easily have been that twin, with her flowing long hair that curled at the ends and her model-esque features.
Jennifer quickly introduced us. Jennifer had her arm around Monica’s waist as they both stood in front of me.
“Is she not the cutest?” Jennifer gushed. “She is the one I was telling you about.” I didn’t have a clue as to what she was talking about. I guess the blank expression on my face probably gave things away.
“She has a crush on you,” Jennifer declared.
“Just a small one,” Monica blushingly replied. Suddenly, I remembered her from the patio conversations we have briefly enjoyed several night before.
Monica was dressed the same as Jennifer in very provocatively cut-off blue jean shorts and a very tight form fitting t-shirt with a major league baseball team logo emblazoned across the front of it.
“So what are we doing?” Monica asked Jennifer as they both stood in front of me.
“Stripping,” Jennifer replied.
“Him or us?” Monica replied.
“Both,” Jennifer shouted.
‘Hell yeah,” Monica replied, quickly stripped out of her t-shirt and unfastening her brassiere. I watched as she let the garments fall to the floor and she bared her luscious 36-C cup boobs, with dark areolas and small pencil-eraser tip-like nipples perched on top of her globes.
Monica didn’t waist any time. She unsnapped her cut-offs and slowly and very suggestively began to peel them down her long tanned legs. I was awestruck. She had a on a tiny black thong that barely covered what needed to be covered. Her cut-off shorts fell to her ankles and she stepped out of them, flipping them up in the air and on to the couch beside me.
Jennifer reached over and grabbed her friend’s ass and gave it a squeeze.
“Oh girl!” she exclaimed as she grabbed Monica’s butt check and held on to it. “You have da booty!”
Monica reciprocated by grabbing Jennifer’s ass and squeezing it.
“Let’s see da’ ass!” Monica called out.
Jennifer slowly lowered her cut off shorts. I watched as her pussy came into view. Her shorts fell to her ankles and Monica exclaimed, “Girl, where are your panties?”
Jennifer pirouetted around and asked, arms extended and palms upwards, “What panties?”
I was speechless, completely and utterly speechless.
Jennifer stepped back between my legs, pressing her leg against my inner thigh, smiling. She slipped her fingers down to her vagina and parted the lips, to give me a perfect view of her bright pink world.
“What do you think?” she asked.
I bit down on my lower lip. Oh my God! I was quickly losing control. There was nothing I could do or say.
Not to be outdone, Monica quickly stripped out of her black thong, stepping out of it. One college hottie coming on to you is nice, but two at a time is almost freaking unbelievable.
“So who do you want to be first?” Jennifer asked as she she Monica swayed back and forth in front of me, each straddling on of my legs. Monica kind of forced the decision, planting a foot on each side of my hips as she launched herself on to the couch, her knees straddling me. I grabbed her butt checks and squeezed them as she pressed her pussy straight into my face. Jennifer pushed at her friend’s butt, laughing as she pinned me against the seat back of the couch.
Jennifer fumbled with the snap to my jeans. In an instant, she had me stripped naked, except for my t-shirt, and was going down on my manhood. She was not the least bit shy about it.
Monica stripped out of her t-shirt and tossed it to the side. She was now completely naked. She self-pinched her nipples and peered down at me, my face still buried in her pubes. I sucked on her hood and then I slipped a finger deep into her pussy. She shuddered and let out a deep moan. I worked my finger back and forth as she gyrated her hips to the beat of the music.
I was about to cum. Jennifer’s oral stimulation was more than I could stand, and I think she knew it. She pulled off my cock and sat back, stripping out of her t-shirt. Monica slipped down on my lap, her wet pussy coming to rest against my cock, her luscious soft pink lips begging to be kissed. I pressed my lips to hers and thrust my probative tongue into her mouth. She was on fire! Oh my gawd!
I felt Monica’s fingers on my cock. She lifted up slightly and then pushed the tip end of my manhood into her very moist pussy. I could feel the walls of her vagina clamping down on my shaft, as I slipped deeper inside of her. She gasped for a breath.
“God I hope you’re on the pill,” I remarked.
“I am,” she breathlessly replied, as our pubic bones met each other. Monica dug her nails into my bare shoulders and grimaced as she rocked back and forth on my lap, my tool buried inside of her, her long hair hanging down on her soft shoulders. Suddenly, she tightened up and her entire body shook, as a massive orgasm shot through her. She tossed her head back and let out a deep moan that only pure ecstasy could create. Her entire body shook and then her head fell softly onto my shoulder as she continued to hold on to me, shaking and trembling.
I looked over Monica’s shoulder for Jennifer. She was propped against a loveseat a few feet away, her fingers buried deep inside her pussy. I let Monica slip off of me and on to the space beside me on the couch. I looked at Jennifer and smiled.
Jennifer stood up and approached me, my arching cock still glistening with the love juices of her friend. Neither one of us said a word. She reached out and extended her hand in my direction. I took hold of her hand and stood up. She lead me into her bedroom.
As she extended herself on to her bed, she told me she was still a virgin. I stood naked before her. I couldn’t take away her virginity. She flipped on to her stomach and gazed up up my stiff cock. She took it in her hand and slipped it back into her mouth.
After a few minutes, she looked up at me again and pleaded, “Please fuck me.”
I slipped on to the bed, and against my better judgment, I pushed my steel rod into her very tight pussy. She dug her nails into my shoulders and grimaced. I pushed through her hymen, and her entire body shook as my pubic bone crashed into hers. I pressed my lips to hers, swallowing her tongue as she ushered it inside of me. I couldn’t hold back. I exploded inside of her. As I did, she shook and trembled, holding on to my shoulders and wrapping her long legs around my hips.
“Oh God!” she cried out. “Oh my Gawd!”
I asked her if she was okay and she assured me, breathlessly, that she was fine. We laid there for the longest time, until nature took its course and I slipped out of her. She let out a pretend whimper.
“Oh no,” she whispered. What was done, however, was done.
I quickly got dressed, realizing that it was getting closer and closer to the time when Jennifer’s mother would probably be pulling up in the drive. The last thing I needed was to be caught with my pants down and both Jennifer and Monica in various states of undress or totally naked.
Jennifer asked if I liked the show. I assured her that I did.
“Well,’ she replied, “This one is on me.”
I staggered, literally, out to the car and headed to the house. Once home, I took two aspirins and collapsed on the bed. Several hours later, my wife woke me and asked what had transpired that had made me pass out.
“Work,” I said, “Tough day.”
I love my wife. The back rub that followed was strong and delightful. I felt guilty as hell, but also felt very lucky. I was confused and awestruck – all at the same time. Until…
