I was 29 and moved to a new city for a new job a short while ago. Being a single woman in a new city, I had no one to help me move. Most of it was okay, but some of the furniture would be a hassle. I wanted to avoid hiring movers. That was when I met Mary, who was 45, and her son Tommy, who was 18. They turned out to be very nice people, Mary was outgoing and friendly. Tommy was also nice but seemed a little shy and quiet. He fit the shy introvert nerd stereotype. Mary offered him up to help me move, which I greatly appreciated.

He was a great help. He didn't talk much, but he made the move go smoother. He and Mary turned out to be my next door neighbours.  The apartment building had an unusual design. It was built in a kind of "V" shape. Our apartments were at the bottom of the "V" on the inside of each leg.

One Friday evening I did what a healthy single women does when she has no plans for the weekend. After a shower I picked up my favorite vibrator and started masturbating on the bed. I was on the fourth floor so I didn't bother with the curtains. I don't know how he noticed, if he heard me moan through the open window, or if he just happened to glance in my direction, or if he was just a peeping tom. I turned my head towards the window for a moment, and that was when I saw him. He was sitting in his room, the only room with a direct view into my bedroom. I didn't want to embarrass him, so I pretended not to notice.

At first I thought to stop. But I was just in the right spot feeling the climax starting to build. I am no exhibitionist, but it did add a little extra excitement knowing someone was watching. And it was essentially harmless. I finished myself off and got dressed again. He never knew I saw him. 

The next time I masturbated I thought about closing the curtains. But I decided against it. I have a healthy sex drive and masturbate regularly. Not every day, but a few times a week. Sometimes I would see him in his room watching, but not every time. And I started to enjoy having him watch; sometimes I could see he was masturbating too. I started to make a point of getting undressed when I went to my bedroom, either in just underwear or completely naked. It gave me a rush of adrenaline to show off to him. He never realized I did it on purpose. It became a sort of ritual. I would usually try to catch him in the corner of my eye, just to see if he was there. It added an element of excitement when he was. 

Then one day. I was immersed deep in the pleasures of my body when I looked over. And instead of catching a fleeting glance, I found myself looking right in his eyes. There was no hiding it. I saw him, and he knew it. And he knew I saw what he was doing. I just smiled at him and continued; what else was there to do? He practically threw himself to the floor and closed his curtains. 

That was the end of my shows, for now anyway. And meeting him outside was extremely awkward; he would turn beet red and turn away. I felt sorry for him. One day we met in the lobby, and this time he couldn't avoid me. So I asked to talk to him. I told him I knew he was watching, and that it was okay. I said that after seeing him the first time, I had shown myself to him deliberately. He was so awkward and shy that it was adorable. He told me he was very shy and was still a virgin. I could see him cringe while admitting this. Watching me was the closest he had been to actual sex. It was really cute to hear him say how beautiful he thought my body was. 

Despite saying it was okay, I never saw him at the window again. And as weird as it sounds. I missed my masturbation buddy. One weekend I knew Mary would be out of town, leaving Tommy home alone. I decided to invite him over for dinner and maybe a movie. He seemed a little anxious about it, but he accepted the invitation. The dinner was nothing special and the conversation was a little awkward. But I did get him to open up a little. When we talked about subjects that interested him he became passionate and excited. Eventually I turned the subject on to sex: what he liked, his fantasies and so on. He was still awkward about it, but less than he had been. 

I asked him if he ever thought about how his first time should be. He told me he didn’t really know. It didn’t matter that much, he just wanted the experience, and to know what it’s like and how to treat a woman. I then asked if he would like me to be his first. He blushed deeply and just nodded. I said I would love to be his first. He just looked at me; I think he half short-circuited and half tried to figure out if I was serious. For the record, I was serious. I told him if he felt ready, I would be waiting for him in the bedroom. And then I stood up and walked into my bedroom, leaving the door open. 

I briefly considered stripping down to my underwear, but I didn't really know for sure what he would do. So I just sat at the end of my bed. A minute passed, maybe two. But it felt like an eternity. And then he appeared at my bedroom door. In a shy quiet voice he told me he would like it very much if I was serious. I smiled, got off the bed and walked up to him. I took him by the hand and led him over to the bed. I told him we could stop at any time if he felt uncomfortable. It was okay to stop. Then I leaned in and kissed him. It was a surprisingly nice kiss considering it was his first. I was getting excited; the thought that I was about to be his first got to me. I loved the thought. I stood up and stripped down to my underwear for him. 

I encouraged him to touch me, and caress my body. He did, very hesitantly. His soft touch was almost ticklish. I gently took his hand and guided him over my body, letting him explore me. After a few minutes he grew more confident. After a while he asked if he could kiss my body. I told him to go ahead and do anything he wanted. If he did anything I didn't like, I would stop him. He kissed my belly, my cleavage, my neck and clavicle. It was a delightful mix of cute and sexy. To my frustration he steered clear of my crotch area. I let him explore me for maybe 15 minutes.

Then I asked him if he could undress too. He nodded and started taking off his clothes. He told me he felt shy about his body. But he had nothing to be shy about. He was no Brad Pitt, but neither was he pudgy. He was in good shape, I could almost see the beginnings of a six-pack. Somehow he looked older without his nerdy T-shirt. Not that I have anything against nerdy.

Once down to his boxers, we kissed again, and this time he had the courage to put his arms around me. I was starting to enjoy his touch. After a long kiss. I asked if he would remove his boxers too. And slowly, shyly, he did. I was surprised; he was a lot bigger than I imagined. From his shy nerdy demeanor I had sort of expected average, maybe a little smaller. I know, it was stupid, I don't know why. He wasn’t huge, not the biggest I had. But well above average. And quite thick. 

He was sitting on the edge of my bed and I knelt down in front of him. I asked if he was ready. When he nodded at me, I leaned forward and took him in my mouth. Slowly and gently I began to suck his dick. I wasn’t surprised when he came after only a few moments. It was his first time after all. I looked up at him, smiled and swallowed. He apologized for cumming so fast and said he just couldn’t hold it anymore. I told him it was okay and normal, and to just sit back and relax.

I stood before him again and took off my underwear. First the bra, freeing the boobs. And then I slid my panties off and let them fall to the floor. I got on the bed and lay down. Then I told him to lie down beside me. I invited him to explore me again. He was less hesitant now, more confident with his touches. And it felt really good. He played and sucked on my boobs. I took his hand and guided him down between my legs. I used his hand to rub myself. I guided him to insert two fingers inside me, teaching him how to rub and finger me. Then I pulled him out of me and took his hand again. I held it up to his face and told him to suck his fingers. He did. His eyes were like saucers. Then I kissed him again. He was fully hard again by now.

I gently pushed on his shoulder so he rolled over on his back. His dick was pointing almost straight up, curving slightly to the left. I sat up and positioned myself over him. Looking down on him, I met his eyes; they were fixed on me. Then I slowly, gently lowered myself onto him, feeling his big virgin dick slide inside me. Knowing I was the first woman he was in sent a course of excitement through my body. Once I was sitting all the way down on him I rested for a moment, not moving, just feeling him inside me. Looking down on him, I saw his eyes were roving over my body. I took his hands and placed them on my hips. Then I started to raise myself up again, high enough so he was just barely inside me, then slowly back down, gently fucking him. Luckily he lasted a lot longer now than he did with the blowjob. But it didn’t take too long before he came. He started breathing heavily and his eyes went wide. Then I felt his dick twitch inside me as he came. 

After the fucking we lay next to each other and talked. He actually said thank you. I had never been thanked for sex before, it was adorable. He was still a bit shy and awkward about it. And he really wanted to know if I had enjoyed it too. I could truthfully say I had. But when he asked, I had to admit I didn't cum, but that didn’t mean I didn't like it. 

After he left I took a shower. I got myself off in the shower, reliving the events in my mind. I loved the fact I had been his first. And the age gap was kind of a turn-on too. Nothing wrong or illegal about it. But it did feel a bit taboo. I doubted his mother would approve of it. But I was hoping for a repeat, and maybe he would last longer.