I grew up in a small town in New England in the 1980's. The homes were small colonials on large wooded lots. Everyone knew their neighbors and kids grew up with a sense of innocence. Porn was the underwear section of the Sears catalogue, and anything other than heterosexual sex was not talked about. At eighteen, I still lived with my parents, while my sister had gone off to college a few years earlier. I liked girls and had kissed a few, I'd even gone to second base with Missy Campbell. But other than that, I had no sexual experience other than playing with my dick whenever I could.

It was a quiet Thursday night when the phone rang. I heard my mom answer and talk for a few minutes, but I wasn't listening as I was intently watching my favorite TV show. When she hung up, she came into our wood-panelled den to talk to me.

"That was Barbara Holt, she asked if you would babysit on Saturday night. I told her you would." I was immediately horrified. First, I'd never babysat before. Second, and more importantly, Mr. Holt was a scary guy. It was well known that he didn't treat his wife well, and he often made inappropriate comments to the neighbor wives. No one liked him, but everyone felt sorry for his wife. She was the kind of woman that did what she was told, else suffer her husband's anger. I imagine she called to see if I would babysit because none of the moms would let their daughters do it. I guess my mom figured since I was a guy, it would be okay. I tried to protest, but my mom said she committed and I needed to do it.

When Saturday night came, I walked over to the Holt's house at 7pm. They lived across the street, but with the large wooded yards the house sat back and you couldn't see it from the street. I rang the doorbell and Mr. Holt answered. He was about 5'10", in his early 30's with brown curly hair and a mustache. He never smiled, and wasn't smiling when he invited me in. His wife was in the kitchen and started to go over the instructions.

The kids had been fed and were up in their bedrooms. They were 6 and 8, and I thought it was strange for them to go to bed so early, but everything about this family was strange. She told me they were going to a party and would be home at eleven.

As they started out the door, Mr. Holt glared at me and said, "Don't go snooping around my house." Again, strange, but it put the fear of God in me.

For the first hour, I simply watched TV. But soon the thought of sex was consuming me, and I knew I needed to jerk off. My thoughts turned to Mrs. Holt. She was about 5'3, thin with brown hair. I think she might have been very pretty, but she always dressed in unflattering clothing and came across as meek and timid. Despite this, at this moment in time, I wanted to fuck her. I wondered what kind of underwear she wore. Without thinking, I went upstairs where the master bedroom was to find out.

The kids were quiet and asleep, but I tiptoed down the hall anyway. My heart was pounding as I entered their bedroom and turned the light on. I went over to the wood dressor and opened the top drawer. Inside were Mrs. Holt's panties, bras and some lingerie. Touching her underwear was a rush, and I was rock hard. I don't know why, but I stripped naked and slipped on a pair of black lace panties. My cock was throbbing, but I was having too much fun wearing her panties to jerk off. Soon I was trying on other panties, her bras, and even her lingerie.

I was so engrossed in what I was doing that I didn't hear the car pull up. It wasn't until they came in the front door that I realized they were home. I froze in panic, realizing the situation I was in. After seeing I wasn't downstairs, they came up the stairs. Mrs. Holt went to check on the kids, and Mr. Holt entered the bedroom. There I was, on his bed, wearing a red teddy lingerie, surrounded by panties and bras. I couldn't move and couldn't speak. After a few moments, he called down the hall to his wife telling her I was in the bedroom, and that she needed to stay with the kids. She started to ask what was going on, but he quickly told her to shut up and not come out until he said so.

He closed the door and turned to me. "So you like dressing up like a girl, huh? I bet you want to be treated like a girl, too." The way he said it, it wasn't a question. It was like he was stating a fact. I didn't know what to say, the best I could do was mumble, "I guess so."

"Then I'm going to treat you like a woman, since that's what you want."

With that, he undid his belt, opened up his pants and pulled his cock out. It was 5-6" long and average girth. At the time, I didn't have anything to compare it to other than mine, but it looked big. I was scared, but at the same time I was even more aroused.

He lay down on the bed and propped his head up on the pillows. He grabbed my arm and pulled me over closer to him. He then told me to start sucking his cock. I'd seen a few late-night movies on Cinemax and knew what he was talking about, but the idea of me sucking a dick never crossed my mind. Yet I found myself wanting to suck his dick.

Here was a strong, dominant older man, and I was a submissive younger man dressed in lingerie. Without thinking, I put my lips around his cock. At first, it was just his head, and I really didn't know what to do. Suddenly, I felt his hand on the back of my head, and he pushed me down on his now hard member. I didn't know it until then, but I was born with no gag reflex. My nose was now against his belly, and his dick was in the back of my throat.

He let out a moan and said, "Well, aren't you a good little cock sucker. Who knew what a little slut you are."

He was using his hand on my head to hold it still as his hips bucked up and down, and he fucked my mouth.

I was now a willing participant. I wanted him to use my mouth. The idea of this man using me for his pleasure was exhilarating. He finally pulled me off his cock and told me to lie face down on the bed. I didn't know what he was doing, but whatever it was I wanted it. He got up off the bed, and I heard him open a nightstand drawer. I couldn't see what he got out, but he then walked to the end of the bed and got on it. He reached down and spread my legs wide. He unsnapped the lingerie which had a clasp in the crotch. As he pulled up the lingerie, I heard the snap of a plastic bottle top. I felt his finger rubbing against my asshole. He had lubed up his finger and was now working it in and out of my hole. It felt weird, but it also felt unbelievably good.

He finally stopped playing with my asshole and I felt him reposition himself on the bed. I was still lying on my stomach when he pulled my hips up off the bed and told me to get on my hands and knees. His voice was so commanding I couldn't say no if I had wanted to, but the truth is I wanted to do whatever he wanted. I was up on all fours when I felt him put the head of his cock against my tight virgin ass.

He didn't go slow and nothing about him was tender, he simply pushed his cock into my ass, taking what was his. The pain was intense, but I didn't scream. He started to work his dick in and out of me, holding on to my hips to hold me in place. I felt tears running down my cheeks, but the pain was turning to pleasure. He picked up the pace and brutalizing my ass, and I loved every minute of it. I heard him moan, and I suddenly felt a warm sensation in my ass as he shot his load deep into me. He pulled out, and as he let go of my hips, I collapsed onto the bed. As he walked to the bathroom to clean up, he told me to get dressed and get the fuck out of his house

I dressed and left the bedroom. I walked down the hallway to the stairs and saw his wife peeking out the bedroom door at me. She knew exactly what he had done to me but didn't say a word. She lowered her eyes and closed the door.

All I could think about on my walk home was what a lucky woman she was.