Educating Tom

What a lovely feeling, our pubic areas were pulled together and we were separated by only a few layers of cloth.

"Maybe we'd better go in." I suggested.

"That sounds like a winning idea." He answered.

As we went upstairs Art and his friends were coming out of the dining room. I smiled and waved at them, which they returned. They knew where we were going and must have been shocked at the realization that we were going upstairs and would soon be in bed fucking. Actually, I could have handled Art. He seemed like one of the many men I'd had sex with, and it might have been fun. But not as much fun as I was going to have with Tom.

Once inside the room we kissed and Tom was ready to start fucking. I could feel his hard penis pushing into me, but I wanted to do something to further his education.

"I want to try something new Tom." I told him.

"What else is there?"

"Anal sex."

"Anal? You mean fucking your ass?"

I explained that I'd go into the bathroom and clean up so that there'd be no nastiness, which could happen sometimes. I took an enema and washed myself really well, that took a tube of lubricant and went back to the bedroom where Tom was lying on the bed with his big penis sticking straight up. I wondered if I'd be able to handle that beauty, but knew I had to, I'd committed myself.

I explained that I'd kneel on the edge of the bed. He should put a big glob of lube on my anus, and slowly work his fingers into it and stretch me. After that he'd start to stick his penis into me.

Tom was reluctant but agreed, so I knelt on the edge of the bed and felt him put a blob of lubricant on my anus. It was cold and made me shiver. The next thing I felt was his finger working there way into my hole until it seemed as if he had two fingers in me. My heart started to pound when I felt the pressure of his penis on my anus.

"Tel me if it hurts." He said. "You feel very tight." And I was even though I tried hard to relax.

"It's okay, I'll try to relax. Don't be afraid to push hard."

I felt him push and then it came. I felt a sharp pain as he penetrated me. More pain, but this was part of it, a masochistic pleasure knowing I could handle it because I'd had it before; that it wouldn't actually split me open.

"Oh God that hurts." I blurted out. I felt his penis pushing deep into me.

"Shall I stop?" He asked.

"No my love. Push harder. The pain is part of the pleasure. Fuck me, Tom. Fuck my ass. Fuck it hard."

I grunted and groaned as I felt his big cock stretching me, plunging deep into my body. The pain subsided somewhat as the excitement and pleasure grew. I started to have a feeling like an orgasm welling up inside me. He was deep, deep inside me and with each plunging stroke his balls slapped against my labia.

"Charlie, Charlie," He said. "This is so good. Your ass is so tight, so good. I want to fuck you hard but tell me if it hurts."

I felt a huge orgasm welling up inside me. "Fuck me hard Tom. Ream my asshole with your huge cock!" I begged.

Then it hit! A gripping orgasm. My back arched and snapped involuntarily and my anal sphincter grabbed the cock that was plunging inside me. It was no longer Tom, it was just a cock and I'd become an animal.

As my orgasm subsided I felt Tom's cock splatter inside me.. It seemed to be filling me with his slimy liquid. I collapsed on to the bed dragging Tom and his lovely cock down with me.

We lay in a heap with his penis still firmly stuck in my anus, and lay there several minutes in the warm orgasmic afterglow. My anal muscles still twitched and gripped him as his penis wilted.

I woke in the morning to find Tom's hand under my nightgown caressing me. "Greedy boy." I laughed "you want more, don't you?" I rolled over on my back and opened my legs for him.

We fucked, a nice calm, loving fuck. It was so nice holding his young body between my legs, both while he fucked me and afterward as we lay together. But it was time to go down for breakfast. The week-end was coming to a close, sadly, and all to soon, by ten o'clock, we were on our way.

I was prepared for whatever might happen on the drive back, and had put on a short denim skirt without underwear and a lightweight shirt without a bra. We hadn't gone far before Tom's hand was under my skirt all the way. The air felt good blowing up between my legs through the open window -- no air-conditioning in Tom's car, and soon we were whipping along with my skirt pulled all the way up and everything on view.

"Don't have an accident, Tom," I laughed. "This would be hard to explain."

As we drove I tried to calculate how many times we'd had sex since we left home but lost track. It was somewhere between ten and fifteen. I shut my eyes and leaned back, with one foot on the dashboard and my body swiveled toward Tom. He was fingering me. That felt so nice, and I knew we'd have to stop somewhere for just one last go.

We pulled into a rest stop where there were a couple of picnic tables. The hotel had made us sandwiches and we had a couple of cold drinks. We had lunch and were going to get back in the car when Tom stopped, turned around and said:

"The picnic table. Come on, Charlie, bend over the picnic table."

"Are you serious Tom? You want me to bend over the table?"

I turned around and went back to the table. I stood there at the end for a moment then leaned over and lay flat with my bottom sticking up.

"Like this?"

"Oh yes, lovely."

I felt him come up behind me, lift my short skirt and push it over my back so that my bottom and everything was exposed. I felt him caress my bottom and I spread my legs as I felt his fingers brush my labia. His penis pressed against them and started to push in. I was already wet and it felt so nice as he penetrated me.

Cars were going by on the road but we weren't in plain view. But then someone else stopped to use the toilet and I heard them talking. They must have been a young couple because they laughed when they saw us, but Tom just kept on fucking and I kept on enjoying it. Another car pulled in, paused and I heard doors open followed by some low voices, doors slamming and they left again.

I was getting a little anxious that someone might report us, but then I felt Tom start to slam into me harder and groan as I felt his hot liquid spatter inside me. He paused then pulled out slowly. I got up stiffly and felt his stuff dribble down my leg. As I was pushing my skirt another car pulled in. Tom was still zipping up his pants when a man got out of the car, smiled and waved and went over to the toilet.

Soon we were back in the car and on our way. We reached home in an hour. Tom and I exchanged a passionate kiss, I got out with my bag and in a moment he was gone.