His first time

A friend told me this story. It was hot enough to share:

I was sixteen and played trumpet in a high school jazz band. We had been hired by the sophomore class at a high school in Ohio to play for their prom and it was a long difficult gig (long bus ride from plus a 3 hour on-stage performance.) After the gig we returned to the motel still excited about getting paid for what we loved doing. Some of us went to a bowling alley to relax and wind down. Someone, I think it was either Don or Max learned of a “whore house” nearby. “Triple Dog Dares” followed “Double Dog Dares” and I wound up in a taxi with a bemused driver. My friends were financing the adventure to the tune of 20 bucks

He drove a couple of blocks, turned into a back alley and stopped behind a nondescript looking house. “Here you go son, that’ll be $3.50” I slipped him a five and walked tentatively up to the back door of the house. My teeth were chattering even though it was not cold. The door opened to my ring and I almost jumped out of my skin. An elderly woman dressed as a maid beckoned me in. I hesitated a moment but gathered my courage and was ushered into a waiting room.

To my surprise, there were two other members from the band sitting there: Jim and Bill both played in the sax line and if anything they looked more frightened than I was. I sat on a weathered couch and tried to read an old Playboy magazine – pausing deliberately at the centerfold and wondering what was in store for me.

The door opened and a gorgeous blonde sidled into the room. She wore a strapless form fitting sea green dress that hid nothing and revealed lots. She was about 5’4” and had a lovely figure with impressive cleavage and seductive hips. “Who’s next?” she said in a throaty voice. I looked at my buddies but they had raised their magazines defensively; hiding their faces. I stood. “I guess that’s me,” I said. She beckoned to me, turned and, showing a fabulous back, flowed out the door.

She ushered me into the room next to the waiting room. “Hi, my name is Lori. I’m 28” she said with her eyes twinkling, her voice a rich dark contralto. “What kind of party do you want,” she said smiling up at me. I stammered “Hi, I am Jack” and something to the effect of “What are my choices?” She cocked her head quizzically and replied, “Well there’s an ‘Around the World’ for Fifteen dollars or just a ‘Regular’ for twelve.” I had no clue as to what either of those meant so I mumbled, “The Regular I guess.”

She giggled “You don’t have much experience, do you?”

“No ma’am, this is my first time.”

That set her back, “You’ve never been with a working girl?”

“No, I have never been with a woman before,” I stuttered while handing her the money.

“You mean I get your cherry?”

I nodded dumbly. She grinned up at me, “Don’t be nervous, Hon, we are going to have fun.“ With that she turned for the door and said over her shoulder, “Take your clothes off and put them on that chair, I’ll be right back.”

It seemed like an eternity while I undressed and carefully folded my clothes over the chair. By now I had a painful erection: My cock strained and elongated like never before. I stood, shivering again and wondering how long it was going to take when the door opened suddenly and Lori slipped in. She saw me and giggled, then she unzipped the front of her dress and stood before me, gloriously naked: No bra, no panties no stockings. She wore only her pale green high heeled shoes and a bewitching smile. Her breasts were full and pointed: her nipples pink and erect. Her stomach was flat and her pubic hair matched the blondness of the hair on her head. She walked toward me, holding up her hands, hips swaying, full breasts all a-jiggle: a powerfully erotic sight.

“Let’s have a look at you,” she said and grabbed my cock with her left hand. I almost fainted with the sensation of it all. Her bare breasts jiggled while she stroked my cock two or three times. “

You have a very nice cock,” she said, “I doubt that you’ll ever have trouble with women with that tool of yours” I groaned. She squeezed hard and pulled on my now engorged cock and looked critically at the head of it, searching for signs of any discharge.

Seeing none, she dragged me over to the sink like a “pull toy” and began washing my cock and balls with soap and warm water. Afraid of finishing too soon, I groaned again and she said, “Be patient, we’ll get to the real thing in a minute. She dried me off, reached up and patted me on the cheek, “Let’s get busy.” She grinned, and turning, slipped out of her heels, lay down on the bed, and beckoned me over.
I knelt between her splayed legs while she reached down and guided the head of my cock to her waiting cunt.

“Go ahead and push.” she said. I pushed gently and easily slid in up to the hilt. The sensation was amazing. I was buried balls-deep in the slick warmth of her and it felt wonderful. I eased forward onto my elbows and stared down into her blue eyes as I registered the amazing feeling of her pussy: she clenched her pussy muscles twice, squeezing my cock. “Come on, Hon, let’s fuck” she whispered hoarsely. Her hands guided my hips into an easy rhythm. For the first time, I felt powerful in the embrace of a woman.

At first, I tried to keep a slow steady beat, but as my passion and my power rose, my thrusting became more insistent and faster. She was holding my face with both hands now, “You won’t have to jack off any more” she whispered. “I’ll be jacking off remembering this for a long time” I groaned in response. Soon our conjoined rhythm became more intense; I was slamming into her with all my strength. My balls were slapping her cunt with a wet squishy sound. The bed was squeaking and banging the wall with my efforts. She gripped me with her legs wrapped high around my waist — her knees pressed tightly to my ribcage, her heels hooked behind my thighs.

“Come on Hon, give it to me — give it to me — I want it.”

I drove myself harder — striving for my finish. My whole world shrunk into the sensation of our fucking: nothing else was perceivable. Her breasts moved in circles under my chest: her erect nipples traced lines of fire around mine. Her arms were locked around my shoulders. She was beginning to pant: her eyes closed and she stretched her head back: neck tendons taut and rigid. Her mouth was open and she was grunting to my thrusts. Her hands moved to my butt and she made me understand the urgency of her rhythm. Her hips worked in counterpoint to mine. She whimpered and moaned with the pleasure of our coupling. I felt her pussy contracting around me: she began to jerk and spasm.

She groaned into my ear: “Come for me Jack, come for me now!”

I felt a small ball of electric fire ignite at the base of my spine. It grew slowly and spread to the whole of my groin. Panting and gasping I rasped, “Oh Lori, I’m gonna come!” Lori dropped her legs from around my back, planted her feet on the bed and levered me up into a kneeling position. The electric fire in my groin consumed me, my face contorted into a grimace and I came hard: jerking and grunting as the bolts of come shot out through my cock into the depths of her. My whole body contracted with each discharge – It felt like I was ejaculating white hot pearls through my cock. At each pulse of my cock, she squeezed me with her pussy, milking every last drop.
We were still locked together, I was panting and sweating. I fell forward onto her and hugged her.

Lori gently wiped my forehead with her right hand. “There, that wasn’t so difficult was it?” she said, letting her legs slide down to the bed. “Thank you Lori, thank you,” I croaked. I was overwhelmed with gratitude to her for her gentle but erotic tutoring. We held still for a moment, then she gently pushed me away, “Get dressed, we’re done here.” There was a sadness in her voice: a recognition that we would never meet again. When I stood and started dressing, she quickly zippered into her green gown and left the room.

I don’t remember leaving the place, I suppose I found a cab and went back to the motel. The next day on the bus, my friends started to kid me in front of the rest of the band about my "adventure." I could only stare out the window, smiling, day-dreaming of how I lost my cherry. The vision of Lori's face, framed in blond curls, contorted in pleasure, swam in my imagination. I was so distracted that they realized I was not going to respond to their taunts, and so, losing interest, they left me alone: to dream and remember.