Between my junior and senior year in 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 a 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
teammates 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
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
my 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 “stuck 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 even
started kissing my dick. 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 cum into 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 into the wrong room
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
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 way 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 cheerleading practice 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 teen 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 cheerleading and swim team. She didn’t have
a lot of pubic hair yet, so I could see her pussy lips as we got wet together 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.
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 can’t 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 think she had a small
orgasm - but I’m not sure. She said, “Let’s rinse off and get out and dry each
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 of things 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 very
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 I’m
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
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 try, 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 do worry about
falling in love with a girl who can’t handle my dick size.