My First TimebyBoakester©
The summer after my graduation from high school, my parents went to Europe for 6 weeks on a vacation trip. They arranged for me to stay with my mom's sister who was divorced and her daughter, Angie, my cousin and my same age.
Since I was very shy around girls, I was still an eighteen year old virgin and really hadn't even dated yet. I had learned to masturbate though, and did it a lot like most boys do. I spent all my energy playing sports and was pretty athletic. My highschool teammates had teased me a lot when we were in the showers and called me "pony" since my dick seemed to be a lot bigger than all of theirs. They said girls were going to really love it when I finally got around to having sex. It was not only pretty long, but was very thick as well. It was very embarrassing though when for no reason it would get hard and huge and stick out and up in the showers with other guys around, and I would always get lots of wise cracks from my team mates.
Well, as I was saying, that summer I "moved in" with Angie and her mom. I was given a room in the basement, while both of them had bedrooms in the 2nd floor. On the 3rd night I was there, we were all watching TV in the den and getting to know each other and having fun and laughing a lot. My aunt finally said she had to go to bed because she had to leave for work early the next day. Angie and I kept watching TV and talking about lots of things, including sex. She said she had had sex a couple of times, and finally got me to admit I was still a complete virgin. She couldn't believe it, saying I was good looking and an athlete. She offered to teach me a few things if I wanted her to, and naturally I said "Oh Yeah, great". The talk had "turned us both on" I guess.
She said she would go upstairs and go to bed and pretend to be asleep, and for me to sneak up to her room in about a half an hour. Since her room was next to her mother's, I must be very quiet and not turn on any lights. I was to take my clothes off and climb into bed with her and she would start "teaching" me about sex. Wow!..I could hardly wait.
I went to my room and stripped to my boxer shorts and lay on my bed. I got a tremendous hard on just thinking about what lay ahead. After a half hour I tip- toed up to the 2nd floor in my shorts with a tremendous hard-on sticking out the front fly hole. It was very dark in the house and I was knocking against furniture all the way.
When I got to Angie's room I opened the door slowly, so as not to make noise. When I closed the door it was pitch dark and I couldn't even see my hand in front of my face. Angie was making noises like she had fallen asleep, but since she had told me to come up, I dropped my shorts and went over to Angie's bed and slipped under the covers with her.
I cuddled up next to her and started to slowly play with her breasts to gently wake her up. Her tits felt much bigger than they had looked like they would be downstairs with all her clothes on, but they felt great - so soft and smooth. I wished I could see them, but it was too dark. I massaged them and started to play with her nipples, and surprisingly, her nipples got hard and much bigger and "stood way out" from her breasts. Wow they felt great. She was still pretty much asleep, but was responding to my hands by moaning in her sleep and slowly moving her body. She sleepily rolled over to face me and gave me a slow kiss and stuck her tongue in my mouth and rolled it all around - I responded by doing the same back to her. While we kissed, I kept playing with her breasts since I had never done it before. She slowly reached one of her hands down my stomach to my crotch area. She tickled my pubic hair and then touched my dick. She gasped - even while she kept kissing me.
She gripped it and it was rock hard and throbbing. Now she started sliding her hand up and down its length and squeezing it as she went. I whispered "Teach me" and she started kissing my body all over; my chest and stomach, and then started kissing my dick even. She was actually kissing it and licking it at the same time - it felt wonderful! She then started putting my dick in her mouth and sucking on it in addition to licking it. I felt like I was about to cum and I tried to hold it back, but I couldn't. I exploded in her mouth while she was sucking it, but instead of moving away she actually sucked it all out into her mouth and then swallowed it.
She kept her grip on my dick and moved back up to kiss me again - long and wet and hard. Amazingly my dick stayed rock hard - not like when I masturbated back home - wow!. After a few minutes of kissing she put my hand between her legs. Her pussy was very wet and soft. Her wetness was actually all over the inside of her legs. I wished I could see it, but I couldn't see any part of her it was so dark, and we weren't talking so we wouldn't wake her mother. She would grip my dick with both her hands and still suck the top half of it . She then rolled me onto my back and held my dick straight up and straddled my body. I couldn't see, but she was putting her pussy over the top of it and was letting herself down on it slowly. She let herself go all the way down on it and gasped and said "Oh God, Oh God" fairly loudly. It was then I realized that it was not Angie, but her mother, my aunt Sarah!! I had gone in the wrong room by mistake!
I really didn't know what to do. But my aunt was really going up and down and rocking back and forth on my hard dick now and moaning and saying "Oh God" a lot. AND, It felt soo goood! She leaned forward and swung her large tits against my mouth and said "suck and kiss them". I put them in my mouth and sucked while she kept rocking on my hard dick. It took a long time this time since it was my 2nd, but soon she said, "I'm cumming....I'm cumming!" Now I was afraid we were going to wake Angie up. She shuddered violently several times, but kept right on going riding my dick. A while later, she said "I'm cumming" again, and it was more violent than the first time. And this time I exploded right with her - inside her hot wet pussy. It was really awesome!!
She fell off and cuddled up beside me and kissed me on my cheek. She said I had the biggest dick she had ever seen - much less touched and fucked. She said it had been a long time since she had had sex, since she had been divorced for several years. She said since I was obviously very shy, she couldn't believe I had the nerve to just come into her bed and start making love to her. Obviously, I couldn't tell her about mine and Angie's plan. She said she would have sex with me the whole 6 weeks I would be there if I wanted. Of course I said great. I told her I was a virgin though and didn't know much about sex. She laughed and said with my "equipment "she would be happy to teach me all she knew.
My dick had finally gone soft after that 2nd time and I figured that was it for the night, However, my aunt said she bet she could get it up one more time to show me one other way. I said OK if she would turn on some lights so I could see her naked. She turned on the bed lamp - and she was really great looking. She was probably maybe 10 or 15 lbs overweight, but in very good proportion. She had very large breasts that still mostly stuck out and had large pinkish brown nipples. Her nipples were hard and still sticking way out from her excitement I guess. Her pubic hair was brown and thick and in an almost perfect triangle on her lower stomach.
She played with my dick and sucked on it and in no time at all it was rock hard again. This time she got on her hands and knees on the edge of the bed and had me stand behind her and between her legs. For the first time ever I got to see a real pussy in person (not magazines, movies, or internet). It was very sexy looking and I could see her lips and her pink area where they slightly parted. I licked it to get it even wetter and so I could see it up close. It was soft and silky to touch and actually tasted pretty good. I used my fingers to part her pussy lips and placed the head of my dick against her pink opening and slowly pushed it into her again. It was very wet and very hot and again she gasped as I drove it deep into her. I slowly stroked her all the way in with my full length. I could see her big breasts and they were hanging down and swinging with my rhythm and motion. I reached around her and squeezed both of her breasts with both my hands. And I gently pinched her hard nipples. Then I held her big beautiful butt in my hands so I could hold on and stroke her deeper. We did it this way (doggie style she said) for a long time. She then told me to try moving my dick up to put it in her other hole above her pussy. I pulled my dick out and lined it up with this little hole and shoved... but my dick was just too big. She turned and put her mouth on it to get it very wet for another try - but no way - my dick was just too big for that small hole. She rolled over then and put her legs up on my shoulders and guided my dick back into her pussy. She told me to pump as hard and deep and fast as I could until I came. I did and we both groaned with ecstasy as I stroked her hard and deep. We again came at the very same time. I was as exhausted as if I had just finished a football game. I staggered back downstairs to my room and slept like I was dead.
The next morning at breakfast Angie asked me what happened to me and why didn't I come to her room as we planned. I told her I "bumped into" her mom when I started to her room and was afraid she would catch us. She said she had to go to her part time job this morning, but would start "teaching" me when she got home around noon. I said great (I really needed some sleep to recover from last night anyway).
She came home at noon and suggested we take a shower together to break the ice and make sure we were clean and smelled good. We undressed and stepped into the shower together. Angie looked like the cover of a magazine. She was very trim and in great shape. She had very nice C cup breasts - firm and high. She was on her way to being as large as her mom some day. She had a very well proportioned figure from high school cheerleading and swim team and had won a partial scholarship to college in the Fall. She didn't have a lot of pubic hair, so I could see her pussy lips as we got wet in the shower. She reacted and was staring at my soft dick and commented that it was the largest she had seen, but that wasn't very many as it turns out. For a couple of eighteen year olds, we were pretty inexperienced, I guess.
She suggested we wash each other to get used to our bodies. She soaped me up first and really seemed to enjoy it and it felt good to me too. She covered every inch of my body which is very muscled from all my sports activities. She said she really loved my tight butt and spent a long time soaping it up. And then she turned me around and started soaping my dick and balls. She said they were a lot larger than what she had seen with the two neighborhood boys she had played around with so far. I cant believe I didn't get a hard on as she washed me, but I didn't - I guess due to the last night's activity with her mom.
She then said "its your turn" and handed me the soap. Wow... where to start! I started with her back, which was trim and muscled. And then her cute little tight butt - I washed and washed it till she eventually turned around for me to soap her front. I soaped her neck and quickly moved to her breasts. I really soaped them up and massaged them a lot - this was like heaven to me. After a while she pushed my hands down to her flat stomach and her pussy. It was very soft and felt so sexy. She moved around as I rubbed her pussy, since I guess it was pretty sensitive, but she said not to stop. I now think she had a small orgasm - but I'm not sure. She said, "Lets rinse off and get out and dry each other off."
We dried off and she had me sit on the side of the bed. I still didn't have confidence that I knew what to do since her mother had taken charge last night. She lifted my soft plump dick and played with it. She also played with my balls. Slowly, my dick finally started to grow and get hard for her. She started to masturbate me like I do at home in my bathroom and bedroom. It got to its full size and she gasped and said she couldn't believe it was so large. I asked her to let me play with her body now, so she lay back on the bed and relaxed. I massaged her breasts and rolled her nipples between my finger and thumb and watched them grow and get hard like her mother's had. I then spread her legs apart so I could see and play with her sweet little pussy. She had neat lips on her pussy which I stretched a little and rolled between my fingers and thumb. She moaned and started to roll her hips and arch upward as I continued to play with her pussy. She took my hand and showed me where her clit was, and told me to include it in my massaging of her pussy, which I did. She moaned and arched until she shouted she was about to come - and not to stop playing with her pussy. She was massaging her own breasts and pinching her nipples while I played with her pussy. She finally shouted "I'm coming...I'm coming" and arched her hips and bucked violently and actually squirted out something similar to my come. It was beautiful to watch.
I had stayed hard as nails throughout her performance and assumed we would now have intercourse. She was obviously still very turned on. However, she said even though she would love to have intercourse with me, she didn't think my huge dick would fit in her small tight pussy and wasn't very anxious to try. She said she would try, but made me promise not to force it and let it be entirely her decision how far to go with it. Of course I agreed and meant it - since she was very nice and was now my good friend. She was still very wet inside and out of her pussy. She told me to put spit on my dick to get it wet and slippery also. She sat on the edge of the bed and spread her legs wide and had me stand in between them. She looked at my huge hard dick and just shook her head and actually looked a little scared. She and I guided the head of my dick to the center of her pussy opening. I applied a little pressure and tried to enter her. No luck. The head of my dick was much larger than her opening and wouldn't even start in at all. She was massaging her clit all the time we were trying, but we didn't even come close and it was hurting her to keep trying so we stopped.
She said she was sorry but would help me come in the other way. So she masturbated me with both hands - it felt great. She said she had never given a "blow job" but would try that for me. She first licked my dick and then tried to put it in her mouth. She did get it in but it hurt her mouth to get even the head in. It looked like her mouth would explode. So she decided to just lick it and keep stroking it with her hands. I finally came a lot and it spurted a couple of feet in the air. We both laughed and admitted we enjoyed all we had done and we did it a lot more that summer while I stayed with her and her mom.
Well her mom, aunt Sarah, and I had all forms of sex almost every night of the 6 weeks I was there. Her pussy was a good fit for my dick and was actually tight and felt wonderful - an advantage of an older woman for me. She was almost 40. Angie and I also had several more "sessions" too, and enjoyed them a lot. But we were never able to have intercourse because of the size difference. I never told either of them about my sex with the other, and am sure they would have been mad if they knew of it, since they aren't trashy or anything. But they are still my best friends and favorite relatives. I hope to visit with them again in the future. And I'm hoping we will continue our sexual "lessons".
But let me tell you - size does matter, and it isn't all good. At least half of the girls I have tried to have sex with now that I am in college, either wouldn't or couldn't because of the large size of my dick. The ones who could take it have said it was awesome. But, in spite of all the jokes, I have missed out on having sex with some fantastic girls, like Angie. I worry about falling in love with a girl who can't handle my dick size. But I hope you have enjoyed hearing about my "First Time" experience.