While I was on my way to play tennis with Ben the first time the day after I had been taken several times during wrestling practice, I learned just how much of a hold Coach Seeman had over me. I was strolling along, racket case under my arm, when a big black limousine, with smoked windows rolled up beside me, the driver's window rolled down, and a big black bullet-headed chauffeur stuck his face out of the window.
"Hey, are you Ron? Ron from the wrestling team?"
"Yeah," I said, breaking my stride in surprise at being hailed, although it probably would have been wise just to walk on without acknowledging who I was.
"Coach Seeman told me to tell you to do it."
"Excuse me? Do what," I said, still confused.
"He just said you'd do it if you knew what was good for you," the chauffeur said gruffly. "I'm pulling over to the far end of this parking lot. Walk over there."
He pulled away and I followed him. The car had pulled up by an unusually high curb, and when I got there and walked around to stand on the curb where the limo was between me and the busy street off a ways in the distance, the rear window of the car came down, and a voice issued from the dark depths of the rear seat.
"Lean in just here and put your hands on the roof of the car. Keep your eyes on the street over there." I did so. The curb was high enough that my pelvis was at the level of the window. I felt my tennis shorts and jock strap being pulled to below my butt cheeks. One thin hand went around to a butt cheek and the other one went up under my tennis shirt and rested on my belly.
My cock was being worked by a mouth, and rather expertly worked, I might add. There I was, trying to look nonchalantly over the roof of the car, while pedestrians passed by in the near distance, looking at me, full of curiosity about the nifty limo over here, while I was getting a very interesting and expert blow job and ball wash and nibble.
When I had come, which was efficiently swallowed, and had been licked clean, my shorts and jock were snapped back into place, I was told to back off from the limo, the back window rolled back up, and limo moved majestically across the parking lot and back into traffic.
There were other peculiar "assignments" Coach Seeman seemed to be volunteering me for among his friends. One day not long after my limo blow job I was accosted by a woman who knew both my name and to drop Coach Seeman's name and his "do it if you know what's good for you" admonishment to get me into her car; and a very nice car too, a big white Bentley.
The woman looked nice and rich too. She was on the edge of being a matron, but money had kept her on the well-maintained side. She was in great shape and would be very attractive in candlelight. And, knowing by now that this was probably leading to sex, I certainly was ready for a change of pace.
It took us more than five minutes just to drive from the road up to her big house on a hill. As we walked up to the door, it opened and it all came together for me. Standing in the door, welcoming us in was one of the school's prize wrestlers, Samir, who we called Sam. A tall, rangy son of the Levant, Sam was a cream and coffee-colored hottie, with strong legs and a long, lean torso topped with broad shoulders and tremendous biceps and pecs. It appeared that in this world, though, he was Mrs. Rich's butler.
He was wearing a tight tux shirt with big cuffs and cufflinks and a bow tie, topping a pair of silk, skin-hugging black pants that fit every contour of his body from his waist down to his calves and then flared out to hems topping a nice pair of patent-leather pumps. And it obviously was Sam who had gotten me hooked up with his mistress, although my mind was working double time to try to figure out just what form of mistress she was to him. Sam was giving us a big welcoming grin.
Mrs. Rich led me to a guest room, waved at the closet, and told me to strip and put on the items I found in the closet. She assured me that there were several of each item in there and I should be able to find everything in a size that would fit me. After I changed, she said, I should look over on the dressing table for further instructions. She told me where she wanted me to come after I'd changed and left me in the room alone. I stripped down to my briefs before checking the closet out, enjoying the uncertainty of what I'd find behind that door.
When I appeared in Mrs. Rich's bedroom nearly thirty minutes later, I was wearing a scarlet silky slip, a blonde wig, and a heavy layer of bright red lipstick. Under the slip, I was wearing a black lacy bra and what I'd call black lacy breakaway bikini panties, meaning that they tied at the sides with string and could be easily pulled off. I also was wearing a thin garter belt around my belly, which held up black, fishnet stockings. On my feet were strapped black stiletto heels, which had been a little difficult to walk down the hall in. I must say that this getup somewhat amused me, and I was game to see where this would lead.
I met my double when I entered Mrs. Rich's bedroom. Mrs. Rich herself was identically attired and was stretched out on a chaise lounge facing her gigantic bed. She looked fine in this light, but I wondered if I perhaps didn't look a little bit better. She looked me up and down and told me in no uncertain terms that she liked what she saw. Then she asked me to go over and perch at the foot of the bed, and, after I'd done that, she rang a buzzer and Samir appeared.
