This story takes place right after high school. My best friend Brian enlisted in the Marines right after school. He lived with his widowed mother and his sister Heather. I spent a lot of time with there family. I was an only child, I lived with my single mom, and she was hardly ever around our apartment. A little more about me, I was always shy around girls, I was geeky and puberty hit me late. I was a month away being 19 years old and was still a virgin. Brian was the only friend I ever had. He was a ladies man, he always had girls around him. He got a lot of pussy. If he would have a girl over and be banging her, I would hang out with his sister Heather. Heather was the most beautiful girl I had ever been around, she was a couple years older than Brian or myself. I actually started hanging around her as much, as she would allow. She was 5’9” about 145lbs with huge 38 dd titis. She had a nickname of Miss Titty. I was always looking for the opportunity to see any bit of skin that could. Anyways after Brian left for the Marines, I started taking care of there yard, laundry, and anything else that Kathy, Brian’s moms needed. They lived in a 5 bedroom Cap cod house in a great addition. They let me stay in the den. It had a sofa bed that I could sleep on. I was there most of the time, during that summer I stained the fence, cleaned gutters, mowed the lawn, and help clean the house.
I wanted Heather so very bad, she knew it. I was helping her change rooms. There were 2 bedrooms downstairs and 3 up. One of the rooms downstairs was Heathers dad office. It still had furniture in it. We started on the hot June morning by moving the desk and file cabinets out to the garage. It was a sweaty day, Heather was wearing a tank top, her tits were stretching the material. I couldn’t stop looking at her. There was a small love seat that she wanted left in there. Then we started moving Heather’s dresser, night stands, hanging clothes. The last thing was her bed, she made a comment about maybe letting me sleep with her sometime. As we were lifting up the mattress, one of Heather’s secrets was hiding. She had a silver vibrator and a Playgirl magazine. She blushed and we moved the mattress down the stairs and got it placed off to the side. I gave her a minute head start, before I went upstairs. I walked into room and she was sitting on her box spring looking at the Playgirl. She told me to sit down next to her, she was flipping pages and started teasing me showing me these pictures. She stop on the centerfold and asked if my penis was that big? I was so embarrassed, I was very small compared to that guy. She reached over and tugged at my pants. I jumped up off the bed, she told me she was sorry. We continue moving her stuff, after all the furniture was moved there was some random clothing laying on the floor. I grabbed her clothes basket and picked up all of the dirty laundry. I snatch a pair of her panties and put them in my pocket for latter. I carried the basket down to the laundry room. I went straight to the bathroom, pulled the panties out of my pocket, pulled them up to my nose. I inhaled the aroma of my angel. I didn’t even have my pants down before Heather was knocking on the door. I put her panties back in my pocket and I opened the door. Heather was standing directly outside the door, she hugged me and thanked me for helping her. I went outside to smoke a cigarette, I actually thought I had got caught, I thought maybe she had seen me put the panties in my pocket while in her room. As I am standing outside Darla, Heather’s friend showed up. They spend almost every afternoon in the back yard sun tanning. I am already worked up enough, I am not sure I decided I would go find something to do. I went in to my room and got my wallet. I went out to the garage and grabbed my bicycle decided to go home for a while. It was about 3 miles from Brian’s house. My mother was actually home and all she did was bitch at me. I grabbed a few things from my room , through them in a backpack and headed back to Brian’s. I was about 5 minutes from there when it started to rain, it was torrential. I was soaked in a minute, as I continued to pedal all I could think about was the panties in my pocket. When I got back Darla and Heather were in the kitchen fixing brownies, in there wet bikinis. Darla was good looking, but not even close to how hot Heather is. I hung out in the kitchen for a minute. I went to the den(my room) . I pulled off my wet clothes and pulled the panties out of my pockets, I thought the rain would have washed all of the scent off. I put the panties up to my nose, and they had more aroma than before, I was so hard and being naked I grabbed my cock and jacked off. I blew my load all over her panties. I put on a pair of running shorts and a tee shirt. I grabbed my wet clothes and the soiled panties and head to the laundry room. I started the washer and was putting clothes in, when Heather walked in and she took off her bikini top and then pulled her bottoms down. I had instant wood again, my running shorts tented up. Darla then did the same thing, she handed her bikini to Heather and she put it in the washer. Darla made a comment about my shorts as the girls left the room. I finished loading the washer and went out to watch TV, the girls joined me on the couch. The teasing continued on for the next few weeks. My perverted panty grab, happen time after time. Kathy owned a interior design company and was home a few days a week. The day I was cleaning the gutters, I had a tall ladder to get to the second story. I happen to see Brian’s mom through the window. Kathy had just got out of the shower and was putting on lotion. She was rubbing the lotion into her tits, they were huge. I had never seen boobs that big in my life. I cleaned out the gutters very slow, I kept looking in the window every time I got a chance. I was climbing down and she was standing right next to window. I continued cleaning, for about the next 2 hours. I was putting the ladder in the garage, when Kathy walked out and said we need to talk. Her voice was very stern. I knew she must have seen me peeping in. I had thought that she was going to kick me out. I followed her in the house. She ask me if I like what I had seen, I was honest and told her yes. At that moment I realized how hot she actually is. She is a 40 something Heather, I was mesmerized while we talked. She asked what I had seen, I told her that I had watch her rubbing the lotion in. She once again ask me if I liked it. My dick was getting hard while I was talking to her. She told me that her and her daughter have the same size breast and they share bars, which she wasn’t wearing. She then asked if I liked staying in her house, I told her I did. She told me I need to follow her, so I did. We went into the bedroom, she told me to lock the door behind me. She pulled off her top, her beautiful tits were in clear view now. She told me to sit on the bed. I sat down and she stood in front of me. She told me I could touch her tits. I was so nervous, she reassured me it was okay. I was touching my first pair of the biggest most beautiful tits. I was so nervous, this was the first time I had ever been this close to someone other than my mom. She then took of the jeans she was wearing, she told me that she want me to take her panties off. I was almost shaking, I had a pit in my stomach. As I was taking off her panties i realized that these are a pairing panties that I jacked off into. Now this beautiful lady was standing in front of me. She told me to stand up, and I did. She removed my clothes, starting with my shirt. She rubbed her hands all over my chest. I was trying to explain that I hadn’t ever been with anybody. I am not sure she was paying attention, She pulled off my shorts exposing my little dick. She help me lift up each foot to get my shorts all the way off. She didn’t say anything, she got on her knees and put my little penis in her mouth. My body was shaking, she grabbed the back off my legs to steady me. She was devouring my penis. I was trying to tell her I was going to cum, I almost think she “shhh”:me. She sucked the cum out of me and right down her throat. When she was done , she pushed me back on to the bed. She climbed up next to me and asked me if I like it. I told it was amazing. I asked about Heather, she told me she was going to the movies. I made a comment about my size, she said I was perfect. She loved that fact that she took take all 5” in her mouth without chocking. She went on to tell me that her husband was smaller than me. That was a major confidence booster. She laid back an told me exactly what to do, how to suck on her ear lobes, how to bite her neck close to her collar bone. That had a lot of effect, I continued along her neck, she was moaning and wiggling around. She kept giving me directions, she guided my hand down to pussy as I sucked on her huge nipples. She had her hand on the back of mine, as I was rubbing my non experienced hand around on her pussy. Abruptly she push my hand out of the way and fingered herself. My hand was now on hers, learning. She stopped me for a second to tell me her next request, I had never seen a pussy in real life and now I am going to put my tongue in one. I got between her beautiful legs and was inches away from her happy spot. I did just as instructed, I licked, sucked, and fingered my first pussy. I fingered her faster as requested, she was jittering on my finger. I kept doing the same thing and her pussy was clamping down on my finger. She told me she wanted to feel me. She had me lay on my back, I am sure I was harder than I had ever been. I think I looked bigger in that moment. She started to climb onto me. I asked her about a condom, she said she couldn’t get pregnant. I honestly didn’t care at this moment, she was lowering herself onto my virgin dick. She was tight, I had no idea what to expect, but this is better than I could have ever imagined. She made love to me, I was in a state of ecstasy, she was picking up her pace. Until now this was only a dream. As she was getting closer, she was yelling something. I felt her squeezing my dick, she was having an orgasm. She speed up,even more and was screaming again, this time I understood, she wanted me to cum. I was already, I came right then. She rolled off me and she was holding me and told me she hadn’t had sex since her husband died. She also told me I am only the second guy she had been with. I stayed in her bed that night, she had me go and close my door. She told me that she was so glad that I was first. We made love another time that night. The next few days around Heather were a little awkward, until she told me that she knew. She didn’t go to the movies, she was outside watching through the window. She told me that she wants to try me out before she goes back to college. I spent many nights in Kathy’s room that summer. Kathy taught me so much, as treated me so well. Read more »