After graduation in June, I arranged to meet up with my parents and siblings at our summer home on Long Island for a family reunion. I headed out a few days early to have some private time and enjoy our pool. It was installed several years ago for practices since I was on my high school and college swim teams. No one was expected until the weekend, though there was the chance that my sister and her husband might arrive earlier.
I had just showered after my morning swim and with no one around I remained naked, as I enjoyed the freedom.
My 6' 1' lean muscular frame was sprawled across my bed. I had headphones on and was listening to a CD. I guess, as most guys might, I started caressing my body causing my morning wood to return. I must have been lost in the music and the moment, because I didn't hear the housekeeper enter my room. I almost jumped off the bed when I felt a hand wrap around my hard-on and begin stroking! I opened my eyes to see her sitting on the edge of the bed, eyeing my body and stroking my cock.
She was a beautiful Latin woman, in her 30s, with black hair, brown eyes and dark skin. She said, 'Relax, Papi; I'm here to help.' I'm not quite sure that's what my parents were paying her for, but who was I to complain about getting a hand job!
She gently pushed me back onto the bed and massaged my pecs while fondling my ever-stiffening dick. She cupped my balls and squeezed as she jacked me off. I, in turn, massaged her thighs as she sat next to me, working my way up between her legs until my fingers found her moist, hot pussy beneath her panties. I pushed the crotch aside and ran my fingers across her wet and hairy lips. She threw her head back and moaned when I brushed my thumb over her clit.
She speeded up her stroking and I was really getting in to it when I heard someone say, 'Oh, shit!' Standing in the doorway was my brother-in-law Mike; he and my sister must have arrived during the night. He entered my room and locked the door. He said he wanted to get some too.
My brother-in-law is 27 and new to the family, so I was just getting to know him. He stood in front of the housekeeper and pushed his sweatpants down around his ankles, revealing a rather long, uncut cock dangling between his legs. I was sort of uncomfortable, yet intrigued.
As she continued stroking me with one hand, she reached up with the other and began tugging on Mike's dick; it hardened and lengthened into quite a formidable erection. It was slightly longer than my own seven inches, though mine is much thicker, I noted.
Mike massaged her tits and I continued masturbating her while she stroked both of us. We were getting into it and she shuddered with orgasms a few times. My fingers were really wet from her juices and a squishing sound was audible. Mike surprised me by leaning down, massaging my pecs and pinching my nipples. I was in heaven. I went with it and reached up to massage his butt, as he pumped his cock in and out of her fist.
It wasn't long before he came, sending ropes of cum across the housekeeper's dress and onto my stomach. Feeling his hot cum, I shot my load too. The three of us fell on the bed until we were composed and went about our own business as if nothing had happened.
My brother-in-law and I talked about it once or twice since that day and we even helped each other get off, but that's another story.