I'm Jon, a relatively average boy from upstate New York. I've got dirty blonde hair, broad shoulders and a squishy two-inch penis. However, when it's erect it grows quite a bit, reaching a length of just over 10 inches. Despite such endowment, I've always been really shy and unable to talk to most girls.
This story takes place after I turned 18, one weekend during my senior year of high school.
My friend, Bran, invited me to come over and stay the night one Friday, so after school I walked down the road to his house as it wasn't far. His family lived in a big house with an in-ground pool, so I brought my swimsuit as the weather was quite nice.
Bran had a couple younger brothers and an older sister who was attending community college. His mom was kind of a MILF and his dad was usually busy working and whatnot. I had heard rumors about their marriage, but didn't really believe any of it.
When I arrived, Bran and his brothers were already in the pool, the shouted greetings and told me I could change in the pool house, so that's where I went.
Upon entering, I was surprised to see Bran's mom turned the other way in a sexy black bikini with her wide curvy hips on display.
"Oh, hello Mrs..." I began, but stopped midsentence as she twirled around giving me a nice view of her busty cleavage. Damn did she still look hot with such lovely skin and her auburn pixie cut hair.
"Hi, Jon. Oh, just call me Laurie, I don't want to sound so old. I was just about to change out of this wet swimsuit. Are you going for a dip too?" she said, as I gawked like an idiot.
"Uh, yeah, um, alright, um, Laurie, I'll wait outside." I stuttered.
"Actually, could you give me a hand? I need help with undoing the back." Laurie said.
"Uh, um, sure." I innocently replied, although I was quickly becoming aroused and my dick was probably visibly pressing against my jeans.
Bran's mom turned around and I pulled the string on the back of her top. Her bikini top fell to the floor and she bent over, pushing her butt against my jeans as she picked it up. Only then did I notice that her bottom had fallen too; she must have undone them at the same time.
"Oh, let me help you change too." she offered, and without any other warning, she had my button undone and was unzipping my fly. Laurie pulled my pants down as I just stood there frozen in disbelief and dropped my swim trunks. My boxers were tented out with her face right there, my cheeks turned red.
"I guess I should be a good host and help you with that too." she said as she pushed against the head of my cock through the cotton, letting my dong bounce.
Still petrified stiff, I simply allowed her to further advance, pulling down my boxers, wrapping her manicured hands and then lips around my shaft as she sucked and pumped my member.
She was a pro, swiftly educing a pleasurable orgasm from me as my cum filled her mouth and she swallowed every last drip.
"A favor for a favor? Can you fill me up? Just a quickie is fine." my friend's mom asked as she laid down on top of some pool floats.
"Uh, sure, but, um..." I hesitatingly replied.
"Don't worry, my tubes are tied and I'm clean, we're safe consenting adults here, aren't we?" Laurie continued, assuaging my concerns before I could verbalize them.
"Yes, ma'am. I'd be happy to." I spoke more confidently as I pulled off my shirt and climbed on top of her.
I pressed my cock into her awaiting snatch, which was surprisingly tight. Inserting deeper into her, I heard her whimper ever so slightly. The majority of my dick was inside of her now, so I began to pump in and out of her, hitting just a bit deeper with every thrust. Laurie grabbed hold of the rafts, squeezing them as I plowed her vagina faster and faster. My friend's mom clenched her teeth as her pussy was hit harder and harder. This was the first time I fucked anyone without a condom and the feeling was so much better, I could barely last at all, even after unloading in Laurie's mouth only a few minutes prior and as I reached my peak, she appeared to be nearing hers as well. As I ejaculated, filling up her cunt, her vagina clenched around my dick squeezing it tight as her orgasm hit her.
Although she had great control and hadn't screamed, she was still panting by the end of our little quickie. "Thanks, honey. See you around, and have fun in the pool." she said sweetly, clearly needing time to regain composure.
I, on the other hand, not wanting to raise suspicion, yanked on my shorts and grabbed a couple inflatables as I dashed out into the sunlight.
"What took you so long? Were you jacking off?" Bran called to me as I came out.
"Shut up! Your brothers are here." Bran's sister Bridget yelled at him from the poolside chair she was laying on, wearing sunglasses and a small pink bikini. Seeing her there like that with her nice wavy sweet reddish brown locks, creamy tan skin and slim figure, I thought I would have gotten another boner if not for just cumming twice.
"I was just filling these up a bit." I said, gesturing to the floats under my arms as I threw them in the pool and jumped in.
Bran, his brothers and I played some basketball in the pool for a bit and practiced silly dives from the diving board, trying to splash his sister.
After a bit, I saw Bran's mom walking by, and she shouted: "Hi Jon, having fun boys?"
"Yep!" we all said in unison.
"Alright, be safe, spaghetti for dinner in an hour." she called, before saying something to Bridget who was still tanning by the pool despite being splashed by us.
...
During dinner I felt like Bridget was eyeing me a bit, but I was pretty focused on the pasta as I was famished following the afternoon's activities.
After dinner, we played video games upstairs in the boys' large shared bedroom, some split-screen shooting and racing games like Halo and Mario Kart.
Bridget came through the bathroom that connected that room and her bedroom with a toothbrush in her hand and told us to be quiet because she was going to bed, so I turned down the volume and she smiled at me as some foamy toothpaste started to dribble out of the corner of her mouth. I watched as stuck her toothbrush back in before turning around and leaving the way she came. Then I realized I had lost the race.
...
We went to bed, sleeping on the floor and sofa rather than in beds and woke up a bit before 8am. Bran's brothers put on Saturday morning cartoons and Bran yelled at them, telling them it was game time as he switched to the input channel and booted up the Nintendo. I told Bran I wanted to shower, so he said it sounded like his sister was done showering, so I could go ahead if the door was unlocked and that everything was in there.
I opened the door and closed it, locking it behind me and walked up next to the shower, the bathroom was still foggy. I had my shirt over my head when I heard the curtain slide open and a gasp. "Um, sorry, I thought it was empty." I said quietly, covering my eyes before I saw anything.
"Don't worry, I forgot to lock it and I'm covered up already." Bridget whispered as she pressed her wet hand against my chest, presumably for balance as she stepped out of the tub.
I opened my eyes to see her with sexy wet hair framing her gorgeous green eyes and brilliant smile, clad in only a small towel that barely covered from her chest to her butt.
