Her name was Tiffany Ann Morton. We both came from upscale WASP families. In Middle school, her mother dressed her in boutique clothes with TAM embroidered on the pockets, so she picked up the nickname "Tam". She preferred that because she felt "Tiffany" was too pretentious, even though that's exactly what our families were. Our parents wanted the boys and girls separated after the sixth grade to avoid the distractions of social relationships at school, so we went to separate private prep-schools and had very little social contacts except in public groups. I met Tam at a retro 1950's style chaperoned "sock hop" that students from both Winthrop and Prior schools attended at the end of our senior year.
We hit it off right away. After that, we texted and sometimes talked on the phone but there was little opportunity for dating other than meeting at rare events at Heritage Oaks Country Club, where our parents were members. And we were both much too self-restrained to sneak off to a dark corner for canoodling. The only outlet we had to be together without an audience was when she babysat for her younger brother while her parents went to Heritage on Saturday evenings, which was after I got my driver's license and the Land Rover Discovery my parents got for me as soon as I turned 18. That was prohibited, but I was resourceful and she was willing. I parked my car on the next block and had a quick escape route through the back yard if the family's Lincoln Continental rolled into the driveway earlier than expected.
Even preppy girls like Tam talked about sex and intimacy with their friends, but it was mostly rumor and speculation, along with heavily redacted advice from their mothers; given the nature of helicopter parenting. Those relatively few who were experienced tended to keep that to themselves. But even TV and movies whispered of that mysterious world to Tam. She had to be curious and perhaps even fantasized about it. I had an outlet for sexual discovery. My parents sent me to Raquette Lake Camp, which was actually 2 camps, one for the girls, one for the boys. The counselors exercised due diligence to keep us separated other than at chaperoned joint events. But love or hormones always found a way at Raquette and my training extended well beyond horses, tennis, sculling, etc., by way of late night excursions around the lake. Getting together was much easier when rendezvous could be worked out with our handy smart phones.
The girls who attended Raquette there were often more "sporting" than typical girls like Tam who busied themselves closer to home during the summer. Many of them were "horsey"; the stereotype and reality being that equestrian girls were more accessible and adventurous sexually. Tam might have wanted to go for tennis and lacrosse, but her parents wanted to keep her close and set her up attending day camps closer by. Our late night excursions at Raquette, fun as they were, were still limited by the terror of potential pregnancy. "Pregging out" would preclude girls from getting into the right schools and marrying well; the standard plan for girls at this level for countless years. Nobody wanted to ruin their chances so close to graduation. There was also the ever-present issue of bloodthirsty mosquitoes, which necessitated adventures being relatively brief and mostly covered up. Creative use of blankets did permit canoodling to extend at least wet hands and fingers and the rare and much coveted fellatio from the boldest of the girls.
My babysitting visits were consisting of watching TV, holding hands and sit-up making out. Lately, I had begun some cursory exploration down onto the two small domes of molded plastic foam that justified the breast-darts on her jacket and shirts. Perhaps she let me do that because she couldn't feel anything. It none the less was earning her some points for possible romantic storytelling with her to friends later on and gave me hope for some real intimacy in the future. At night I had fantasized about the tender bits that were under those molded mounds and helped me to siphon off the excess DNA I had accumulated while with Tam before I went to sleep. This Saturday evening seemed to be no different. Tam had come home after her violin lesson and did most of her homework before I got there at 7:30. She was still in her Pendleton skirt and untucked cotton Oxford uniform shirt. There was a Tennis match on the TV. Some spiky-haired woman with a Russian sounding name double faulted, threw her racquet down on the grass and yelled "FUCK!" Tam turned the channel during the commercial break to a movie called Miss Congeniality. She seemed interested in it. I tried to be.
I was thirsty and got up to get something to drink. I opened a cabinet for a glass and there were 4 large bottles of "Jack Daniel's" there, one half-empty. My father drank bourbon; "Jim Beam". They looked about the same. When I was at home alone, I mixed it with Coca Cola or Sprite; diligently refilling the bottle to the exact level as it had been with water and placing it precisely as he had left it in his liquor cabinet. The buzz I got from it was relaxing. You kind of look at things differently, which was refreshing. I poured one like those at home for myself and one for Tam. I hadn't asked Tam first but I thought she might want to try it. I refilled the bottle and re-positioned it like at home. I brought the glasses back to the TV table and set them down. Tam looked at the glasses and then at me. I told her what they were. Tam was not a wall flower, just heavily regulated. She played sports and did English style horse riding. Although she was cautious, she wasn't closed minded to trying things out. So up the glasses came, we clinked them and I said "Cheers!" like they did at the club. The flavor was sweet and tart, cold and hot at the same time. After her initial reaction, she liked it and it was not long before the glasses were empty. Nor was it long before we both felt a rush from them. An empty stomach will do that. It was a warm, relaxed feeling with some "oh, what the hell" mixed in.
Tam and I started making out like we often did, but it was different this time. I had a strong feeling of wanting her. The drink helped to release the feelings and desire i had for Tam. She seemed to be responding like she felt that way, too. I wanted to feel her presence, her sweet fragrance and her warmth. Our kisses became wetter and longer. Between them, I smelled her hair and nuzzled her neckline down to the first button down below her collar. A close, warm, sweet essence met me there. I felt a stirring down below. This was a lot like fantasies I used to bring me through masturbation, but it was real. I took the chance of placing my hand below her foam-encased breast to lift it up and kiss it through her shirt. Much as I liked doing it, there still wasn't much of a human feeling there. So I returned to kissing her. While I did, she deftly reached inside her open collar, gripped firmly on her bra and pulled it straight up toward her neckline. Now those molded foam mounds were just beneath both of our chins. It might have looked funny but this wasn't a time for humor. I had just gotten a green light.
I moved my hand onto her shirt just below her breast and was going to caress whatever I could find there through it. But before I did, she pulled her shirt tail out from under my hand so it lay on her tummy. Of course, I moved my hand up to find the real thing; warm, silky-soft, slightly damp from perspiration and body lotion. Sweet and petite. I lifted it from below and caressed it. There was her nipple. The areola was tightly puckered with the thick little nub, thick, in the middle of it, there against my fingers. This was better than the masturbation fantasy I could ever make up and I felt it down below. I was tight against my jeans. I felt like I wanted to push against something. What I was doing now was exciting but awkward and I felt it must be for Tam too. So I guided her off the couch and onto the carpeted floor so we could stretch out. Tam was with me on this. I began to kiss her again and could alternate caressing between one breast and the other. On her back on the floor, there wasn't much to them but they were the most beautiful breasts in the world at that moment.
I unbuttoned the two bottom buttons on her shirt, lifted it up and could now see her breasts as I caressed them. She had creamy white skin and pinkish brown nipples. I began to gently suck on one while I caressed the other. Her breath quivered and she placed her hand on the back of my head while I did it. I stayed with this foe a while, savoring the feel in my hand. But now I was heading into uncharted territory and might be turned away. I made my way down to her navel, kissing and tonguing it like a tiny mouth, and then down to the waistline. Tam's body stiffened and she crossed her ankles. What was I thinking? It was pretty clear Jack Daniel's was doing my thinking for me. I was about to go to a place I had never been before and barely knew what to do. I followed my instincts, remembering a few AV clips I'd seen online. While kissing at her waistline, I pulled up onto my knees, bending down to continue caressing her breasts and kissing at her waistline. I was about to make a big move and I didn't want to ruin everything and be turned away. I was worried that she would think I was going to try to have sex with her right there on the floor. But she knew I was fully dressed, going slow and gentle and not reaching to undo my clothes.
