The Weekend Sleepover Ch. 01

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All characters in this story series are at least 18 years old

Growing up, my best friend’s name was Mark. We had grown up on the same street and gone to the same school since we were in kindergarten. Mark was the baby in a beautiful family. His father had passed away when we were freshmen in high school, and it was hard on Mark and his family, but his father had left the family a lot of money. His mother, Lisa (who I always called “Mrs. M,” even after her husband’s death), like to stay fit and active. She had been a housewife until her husband’s death, but took over the family landscaping business when she became a widow. She was shorter, about 5’4″, with shoulder length brown hair, kind green eyes, and an amazingly firm looking set of C cup breasts for a woman of 46. She had definitely aged, but she kept in shape. Mark’s two older sisters seemed to have inherited all the best genes from Mark’s tall, blond father and shapely mother. Amanda, or “Mandy,” was six years older than Mark, and I didn’t know her as well. She had the body of a dancer, tall and thin but with a nice, big set of B cup breasts. Mandy was almost as tall as Mark, at 5’10.” She had her father’s blond hair and her mother’s green eyes. Mark’s other sister, Jennifer (or “Jenny”) was shorter than her brother and sister at 5’6,” but had a nice, shapely body. Jennifer shared her sister’s blond hair and green eyes, but had a large set of C cup breasts and a cute little apple bottom.

I had known Jenny growing up, especially since she was only two grades above us. She was a cheerleader in high school, hung out with the popular girls, and always liked to tease her “baby brother” and I whenever we were at her house. Jenny complained constantly that she was the fat sibling, since her sister was so tall and thin and Mark had developed into a muscular young man. I thought Jenny was beautiful. She wasn’t the stick figure of a skinny, high school girl growing up, but she had the body of a beautiful woman. I had told Mark that I thought his sister was hot, and like most high school kids, he didn’t want to hear about boys checking out his sister. So I never brought it up again. As an 18 year old with raging hormones, being around Jenny often turned me on. She and her cheerleader friends often wore skimpy clothes or practiced their stunts in tight little cheerleader outfits.

Then suddenly it was my turn to celebrate graduating from high school. Mark and I were trying to squeeze in as much fun as possible before we had to leave for college. It was a summer full of trips to our favorite places and spending time with our group of friends whenever we could. Jenny was back from college for part of the summer, but she was spending most of her time with her old high school crowd. One week, Mark’s mother had to leave for a business conference in the State Capitol. She said her kids were good, and they were all adults now, so she left it to Jenny to keep an eye on Mark and to Mark to keep an eye on Jenny. They were forbidden from throwing parties, but were allowed to invite a few friends over, and Jenny was given some money for food. Mark invited me over for that Friday night, telling me I should spend the weekend at his house. Jenny had also invited three of her college friends to town to spend the weekend at her place. Mark was thrilled to hear about his sister’s friends, claiming that at least two of them were very attractive and he was hoping to be able to hit on them over the course of the weekend. He said he would kill to be able to make out with a college girl. Little did we know what we were in for.

Mark and I were eating pizza around 9:00 when all the girls arrived. They had brought three boxes of wine and proceeded to get drunk as we all got to know each other over pizzas. Samantha, or Sam as they called her, was clearly the queen bee of the group. She was tomboy-ish, but attractive in a girl-next-door sort of way. She was tall and skinny with long, brown hair, smallish B cup breasts, but noticeably nice, shapely legs. When she spoke, you could tell that the other girls listened. Sam rolled her eyes when the others giggled at childish jokes. When I got to college, I got to know her type. She was the girl who was always taking care of her friends, making sure they didn’t get into trouble. Brenda was a big flirt, and the one Mark had told me he wanted. She was very pretty, with pale skin and blue eyes framed by fiery red hair. Brenda was about 5’6″ tall with a very full set of B cup breasts. Brenda was the kind of girl who looked at you seductively, casually sucked the cheese off her fingers as if she didn’t know what it looked like, and then giggled mischievously while flipping her hair. The third college friend, Carly, was short at about 5’2″ tall. She was the least skinny of the girls, but I never would have described her as fat. She was voluptuous. She had long, blond hair, sparkling grayish green eyes, and an amazing set of of huge D cup Avsallar Escort breasts. Her firm, perky rack matched her cute, round bottom.

As we cleaned up the mess on the dining room table and threw out the empty boxes, it became clear that the girls were drunk.

“So,” Brenda asked casually, “Are you two boys still virgins?”

“What?!” I exclaimed.

“You boys don’t want to start college as virgins,” Brenda continued, “None of the girls will sleep with you.”

“Well, Kevin’s still a virgin,” Mark replied, “But I’m not.” I punched him hard in the shoulder for that one.

“What?!” Jenny exclaimed in surprise. “My baby brother has had sex!”

“Oh shut up, Jenny,” Carly chirped, “You’ve become quite the slut yourself.”

Mark changed instantly from trying to look suave, to trying to control his anger. “What?!!” He roared, “What do you mean a slut?”

“Oh calm down,” Brenda responded, “You were the one just trying to brag about not being a virgin.”

A tense and awkward silence followed. We continued to clean up our dinner mess without much conversation between us. I spent most of my time glaring at Mark, who spent most of his time glaring at Jenny, who spent most of her time glaring at Carly. We decided to move to the living room to watch a movie.

Mark’s living room was large, with two big couches and a Lazy Boy recliner. Mark plopped himself down in the recliner, still clearly irritated. I tried to be polite and waited to see where the girls would sit. Surprisingly Brenda and Carly chose to spread out on the floor. Jenny and Sam sat in one of the couches, so I was left to stretch out on the other couch. We turned off the lights and settled in for the movie. The air conditioning was strong to combat the heat of the summer, and we were soon getting a little cool. There were blankets around the room, and it wasn’t long before Jenny and Sam were sharing one, Brenda and Carly were tucked under another on the floor, and even I was using one to cover me.

The girls were giggly during the movie, and clearly a little drunk. And they were still drinking some of the boxed wine. “It’s getting cold in here,” Brenda complained.

“We can turn down the AC, stupid, ” Sam responded.

“No, I don’t want to get sweaty,” Carly responded with yet another giggle.

“Fine,” Brenda replied, “Then I need some warmth.” In one quick move, Brenda threw off the blanket, jumped up on the couch next to me, and had wormed herself under my blanket. I was caught completely off guard.

“What are you doing, Brenda?” Sam said calmly but clearly disapprovingly.

“I need some body heat, and I’m totally safe up here with the virgin,” She replied. I could feel the heat of embarrassment causing my face to flush.

The movie got interesting again, and the talking stopped, but I wasn’t paying attention to the t.v. anymore. I had never been so intimately close to a virtual stranger before. Brenda had snuggled her backside right up to my front, and I was keenly aware of the slight and sweet smell of her perfume. I could see her womanly curves and feel her soft ass pressed against my crotch. It wasn’t long before I was trying to hide a throbbing erection. M hard cock had grown awkwardly against my leg, and was pressed down by my underwear. It kept my cock away from Brenda, but it was starting to get painful. I tried to shift my weight subtly to free my erection, and it sprang up into its natural position. Unfortunately, the move also caused it to slide against Brenda’s backside and left it snuggled between the crack of her ass. I was terrified she would complain or slap me, but instead, she giggled.

There was no obvious reason for her to have giggled, and I looked at the others in the room. Mark was looking at me with irritation and clear jealousy. I knew he was interested in Brenda, but this was not my fault. Sam was keeping one eye on us and one eye on the movie, but was clearly irritated. I didn’t know what to do, I was trapped. I was loving the feeling of Brenda pressed against my body, but I was afraid the others disapproved and Brenda might think I was a perv with my cock pressed against her.

After a couple of minutes, Brenda sighed. My cock was still throbbing against her when she lifted her arm and absently scratched her thigh. That hand quickly dipped behind her back and between us, and was pawing at my erection. I shifted backwards in surprise, and Brenda reacted by trying to wrap her hand around the head of my dick through my shorts. All that movement did not go unnoticed.

“What is going on over there?” Sam scolded.

“Yeah, Kevin,” Brenda replied, “Stop moving around!”

I froze. I didn’t want to get into trouble and if the blanket were taken away I would sure look guilty with a solid hard on tenting my pants. Brenda slid down so that she was lying on her back on the couch next to me. I could feel the Avsallar Escort Bayan soft weight of one of her breasts now pressing against my chest. That mischievous hand of hers now had easy access to my throbbing cock in the space created under the blanket between us. I didn’t move as her hand closed around it, feeling its weight and girth through my shorts. Brenda wasn’t just playing around. Within second she had deftly pushed down the top of my shorts and had the hard tip of my cock in her small, soft hands. I had gotten hand jobs before, but Brenda definitely knew what she was doing. She held the head of my rod in her hands and just used her thumb to rub gently around the head of my cock. There was no visible movement above the blanket, but the sensations going on underneath were thrilling. It wouldn’t have been enough, with just her thumb circling the head of my knob, for her to have gotten me off, but it sure felt good.

“Can we pause the movie for a pee break?” Carly asked from the floor.

“Sounds like a good idea,” Mark replied, hitting the pause button. Carly and Mark jumped up at the same time and headed to different bathrooms in the house.

“I need some water,” Sam said, standing and heading for the kitchen. Jenny looked at me with the smile that always melted my heart, winked, and followed Sam into the kitchen.

Brenda turned to face me, never letting go of my cock or stopping her gentle rubbing. Her soft, warm hand was starting to feel really good. “So lover,” she whispered, “are you really a virgin?”

“Yes,” I whispered back, feeling the weight of her full breasts pressed against my chest.

“You being a good boy, waiting for marriage?” She asked.

“No,” I replied, “I guess I just haven’t had a chance.”

“So you do want to have sex?” She asked.

“Yes,” I replied

She laughed a surprisingly light, sweet laugh. “Good for you,” she whispered. “Sex is fun. And you don’t want to disappoint all those college girls who are gong to love this hard body of yours, or this big cock.” Brenda’s hand began to slide up and down my shaft, feeling a little rough on my dry skin but feeling much better than just her soft thumb. “My goodness this is a big cock,” she continued, feeling my thick seven inches. I had seen other guys in the shower and thought they looked a little smaller, but I never realized until that moment how large my cock was. “Would you like it if I was your first time,” Brenda whispered, looking deeply into my eyes.

“Of course,” I whispered back. Brenda began pulling off her shorts, and I could tell what she was doing. “Hey wait, what if…” But that was all I got out. Jenny bounced her way back into the room.

“You two having fun?” Jenny teased.

“Oh, just talking about college,” Brenda replied.

“Yeah right,” Jenny shot back with a laugh. Jenny dropped into the recliner, one shapely leg draped over the arm of the chair. With her legs spread like that, I caught a glimpse of Jenny’s pink underwear beneath her shorts. I glanced back up at her face, and saw that she was looking at me. She had caught me staring at her crotch, and instead of looking upset she flashed me a silly smile.

Slowly, everyone else began to return to the room. With Jenny in the recliner, Mark took the other couch. Without a word to anyone, Carly also sat down on the couch and pulled the blanket over her. Sam, the last to return, didn’t seem to mind being left with the blanket on the floor, and spread herself out there. We restarted the movie.

Brenda never stopped rubbing me. Her hands were both soft and strong, never chafing my dry cock but applying just the right amount of pressure to feel good. She was especially adept at alternating between swirling her soft hand around just the head of my cock and taking long strokes up the length of my shaft. I was initially nervous that people would see her hand moving up and down, but the blanket fell in a way that created a little space between us, and it hid her movements completely. Once I relaxed about being caught, I felt more calm and revelled in the feeling of her hands sliding up and down my shaft. I had gotten a couple of hand jobs before Brenda, but nothing came close to how good her hand felt. And she knew exactly where to touch. The soft spot just under the crown of my cock, the sensitive top of the head, the ridge running length of the shaft. Switching up her movements also meant that I was constantly surprised and aroused. It felt like sparks of electricity were shooting through my body every time she did something new, and then I quickly had something else to worry about.

I tried to casually lower my head and put my mouth right next to her ear. “Stop,” I barely whispered. “I’m going to cum.”

“Are you kidding?” She whispered back, “already?”

“Yes, stop!” I insisted. “I’m going to shoot cum all over you if you don’t.”

She Escort Avsallar gave me a big smile and her blue eyes sparkled. “Fine, if you don’t want to make a mess, put it in me.”

“Are you crazy?” I whispered in her ear, but she didn’t respond. She just rolled slowly onto her side, as if she were adjusting herself, so that her bare firm ass was pressed against my throbbing cock. I had forgotten that she slipped off her pants earlier. This was getting completely out of control. I loved the feeling of her shapely, firm ass pressed against my engorged cock. You could have bounced quarters off that ass. Brenda had slipped her hand down her body, because I felt it groping between her legs for my cock. I thrust my hips upward slightly, and her hand found my hard shaft. Her delicate fingers again played teasing circles around the rim of my swollen member. Then, Brenda pulled my fat cock head down slightly and suddenly my cock was rubbing against something wet and slippery. I realized that Brenda had rubbed my cock head against her wet, swollen pussy lips before positioning me at the opening to her entrance. Her hand moved away, and we remained like that for a moment, my throbbing and eager penis positioned just at the entrance to her pussy.

I looked around the room, and no one seemed to notice a thing. Carly and Mark had laid across the couch in a mirror of what I was doing with Brenda. Jenny and Sam were both wrapped up in blankets and appeared genuinely interested in the movie. I didn’t know what to do, but my hard on was screaming for attention, so I pushed my hips forward slightly.

I will never forget the sensation that followed. At first I didn’t think anything was going to happen, as I felt warm and wet pressure on the head of my cock. Then suddenly my cock head pushed through Brenda’s opening, and I was inside of her. It was like my penis had been swallowed by a hot, wet, velvety glove, and I was no longer a virgin. The heat and the wetness and the tightness and the softness were all amazing. I was surprised by how hot and wet it felt, but I knew this is where my cock was meant to be. Even my best jerk off sessions had never come close to feeling as good as a real pussy. I could feel the heat of pleasure flowing through my cock and warming the center of my body.

Brenda sighed audibly as I pushed through, but again no one seemed to be paying attention to us. After I overcame the initial amazing feeling of the warmth and wetness, I pushed my cock fully into Brenda. She groaned very softly, and then I withdrew almost to my tip before sliding the length of my solid shaft back into her tightness. The feel of her wet, tight skin sliding against the length my aching cock was incredible. I would like to say that I was a stud my very first time, and gave Brenda a good fucking before I came, but that is not true at all. The sensation of a wet, velvety glove gripping my hard penis was too much for me. I pulled back, thrust, pulled back, thrust, and then the orgasm overtook me. It happened so quickly, I almost cried out in surprise. I had never gotten off so hard or so quickly in my short life, but each thrust felt as good as ten minutes of masturbating. Every inch of skin on my cock tingled as it rubbed against the soft tunnel of her pussy. After the third thrust, fireworks flashed before my eyes, I felt a heated explosion in my groin, and every molecule in my body was overcome with pure, bright, pleasure. I felt my cock expand and then spurt hot load after enormous hot load deep into Brenda’s tight pussy. It felt like my orgasm lasted for an hour, and I began to feel my body actually shaking as spurt after spurt erupted out of my cock and into Brenda’s pussy. In reality, it probably lasted 30 seconds. But it was far and away the best orgasm of my young life to that point.

As I calmed down and tried to keep from screaming in joy, I began to think of excuses to give Brenda for why I had come so fast. She had given me a really great hand job, for a while. And watching her and the other girls being flirty while eating their pizza had kept me turned on for most of the night. But in the end, it turned out that I didn’t need any excuses.

We continued to lay motionless on the couch as the movie on the television came to an end. My cock softened a little from its fully engorged state, but remained firmly planted in Brenda’s pussy. As soon as the movie ended, Jenny sprang out of her chair and said she had to pee. Sam said she also had to go, and they headed off towards Jenny’s bathroom. Mark and Carly lay on the other couch for a moment before Mark said something, Carly giggled, and then they got up and headed towards the kitchen without a word to me or Brenda.

Brenda turned to face me and my thick cock finally slipped out from inside of her. She had a bright smile on her face as she looked at me with her beautiful blue eyes.

“I can tell you really enjoyed that,” she said, “I can’t believe I could actually feel you shaking as you came. And your cock is still pretty hard. Amazing. Did you enjoy your first time, virgin?”

“Oh yeah,” I whispered back, “I hope that was okay.”

“Oh yeah, baby,” Brenda replied, her blue eyes still intently looking at mine, “I love getting to be your first.”

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