I was laying there in some very transparent red lace panties and Drews’ tee
shirt. Head was really confused with my body and my spontaneous reactions to my
conversations with this cute teenaged boy one bed over. Only hours before I was
in a conservative night gown that more that covered me down to my knees. I felt
both guilt and passion as I heard him sleeping on the next bed over from in our
very upscale hotel room. I balled up in a fetal position with my mind on my wet
crotch and very hard nipples. I am not sure when but I finally fell asleep.
So I am Anna. I am a 44 year old mother of an 19 year old girl and an avid
tennis player. Last summer I started playing tennis with my daughters boyfriend,
Drew, and we began to enter into tennis tournament and win at the club and state
level. Drew is a great player we just seem to work well together on the court. I
have kept playing regularly since playing in college but my skill has faded some
with age and I do practice law.
Over the past two years we have played a lot and trained a lot together and I
have become great friends with his mom, a single parent, and Drew. We have both
had minor injuries and become a little closer and we have had to massage each
other at different times and different parts of our bodies. Which have made for
some embarrassing moments and I have caught glances of things most moms of
teenage girls don’t see of their daughters boyfriends which is also why I became
so focused on him in both curiosity and maybe some lust. During a pulled growing
muscle injury I would help rub his thigh adn when you massage a teenaged boys
thigh things do pop-up and boy did they.
That is when I first noticed that eh was really gifted and I don’t mean for a
boy but foe a man. He has also helped me with a few sore muscles and his
massages stirred things and caused some excitement that was more than just
friendly desires. I also began to notice that he was checking me out as you
would expect a boy to do. He would steal glimpses at my ass, crotch and chest.
At first I would try to slowly change positions to remove the temptation but
over time I began to wear more revealing tops and tennis skirts and panties
rather than shorts which afforded more opportunities.
I was actually getting turned on by his checking me out and I would begin to
give little shows and play it off as accidents especially bending over and
showing him my ass or in front of him so he could see down the v of my top. I
would even wear just a sports bra to practice in the summer and watch him try to
sheepishly check out my rock hard nipples. I am a 5‘8’ tall and measure 32C
(sometimes a D), 22, 31 with dark brunette hair.
Three weeks my daughter broke up saying that she wanted to go away to school,
she is older than Drew, with out and attachments and about the same time Drew
and I entered into the state tennis open challenge and surprised everyone, even
ourselves, by winning through the first rounds. Since we had to travel across
the state for the last matches, we left for the tournament on Thursday to be
well rested. Drew’s parents are divorced and rather than have two rooms and the
expense we just got one room with tow beds. I took the traditional mother type
sleeping gown and just figured he would sleep in shorts.
That first night I was laying in bed extremely uncomfortable since I
typically slept in a thin gown and panties and hated the material around my
body. I noticed that Drew was stirring around so I asked him if he was ok and
found out that he typically just slept in boxers, not shorts and a tee so I made
a deal. He would give me his tee and then he could sleep in just his boxers.
After all, we were in different beds. He took off his tee and tossed it to me
and I heard his shorts hit the floor right after that so a removed my gown, the
room was dark so I just sat up in bed and pulled it off over my head and chucked
it on the floor, and started to put on his tee.
As I did, my body just froze there and I got so excited that my nipples got
rock hard and I shivered and came or maybe peed a little. I glanced over and saw
Drew was looking my direction but other than my partial naked silouette, it was
too dark to make the details out, he couldn’t see anything ..did i want him to?
We chatted for a while about life, dating and I did my normal teasing him
about girls, my daughter and that I knew he was a boob man and who he thought he
should ask out, know he was a boob man, but coming from his former girlfriends
mom that may have been strange even though I did know him well and he know I
would keep it a secret. Secretly, I was glad he didn’t have plans. I knew he was
a virgin but he and my daughter had gone to third base a few times and I also
know that he has a sizable manhood both from seeing it pop-up as I mentioned
before and overhearing my daughter tell her friend that Drew’s penis was larger
than her wrist and really long and much larger than her dads. So when had she
seen my husband Tim’s dick ..a question I wanted to ask but never could figure
out how so I just assumed she had walked in on him changing or showering and let
it go. I was actually getting horny laying there in bed.
Some background. I caught her dad Tim, a physician, in bed with a friend and
tennis partner of mine. I walked in my living room to see her totally riding his
cock as he sucked her tits. I actually saw him fill her bald pussy with his
sperm since I was in shock and couldn't move to leave. She was a screamer, a
squirter and he said he liked her shaved pussy and DD tits. I heard later she
liked it in the ass too. if that wasn’t enough, I later caught him fucking a
rather large, bbw, big tit latin intern in his office on his desk. Her pussy was
hairier than mine and I watched her tits sway back-n-forth as he hammered her.
She was a virgin when they met but was a pregnant slut when the summer was over
and she returned to school. Rather than divorce, we decided to wait until our
daughter had left home for school and he would just file for divorce and move
Back to my story ... Eventually I heard Drew sleeping on the next bed over
and I too soon fell asleep all cuddled up in the fetal position with a wet
crotch and very hard nipples.
I awoke the next morning and, believing he was still sleeping, walked over to
the window to see the city and stretch to wake-up. As I stretched my arms over
my head, which raised the tee shirt up to my waist, I gave a now wide awake Drew
a full view of my 44 year old ass in tight almost transparent lacy red panties.
My mind was somewhere out there thinking about my upcoming match and my growing
attraction to my daughters former boy friend when Drew, said this is was sure a
nice view! I almost jumped threw the roof! I turned around to see him up on his
elbows looking at me.
I told him that he almost scared the pee out of me and as I walked across the
room to go to the bath room his eyes totally covered my body and his complement
about looking as good in the morning as I always do threw me so I had to ask to
to verify that it was a complement. He did and asked if I had been up for a
while to which I said no and that is why I have to go to the bathroom. He said
don’t be long I have to go too and that is when I believe he caught me staring
at the large lump growing larger under the covers. He looked down following the
path of my eyes and was looking back at me when I turned the corner to the
bathroom. I just said boys and the morning stiffey as I closed the door ..I
couldn’t believe i said that!
I really had to go and just the though of him knowing I was peeing was
erotic. When I was done I walked out of the bathroom and told the beautifully
built and bare chested Drew who had an obvious morning erection that the
bathroom was all his he wasted no time and with out even closing the door I soon
heard the steady stream of his pee into the toilet. Without thinking, I walked
to the door to initially see the back of him but turning to look at him in the
mirror I saw the side view of him holding a very large penis and guiding a
steady stream of pee into the toilet.
My knees weakened and I saw him catch me in the door but rather than say
something like “can’t I pee in private” he apologized for leaving the door open.
I went to sit on the foot of the bed and turned the television on to try to
clear my mind as I heard the shower start and stop. As he came out of the shower
with a towel around his waist, a nice bulge in the front and water still on his
tan well-built body it was my turn to say nice view with a wicked grin and I
watched him smile as he once again checked me out as i walked past him to take a
shower and dress.
In the bathroom I took a long look at myself in the mirror and I was clear
why my teenaged Drew was sporting a rock solid hard-on. His tee shirt clearly
did not hide the shape of my rock hard nipples and it was not long enough to
cover the bottom half of my panties, front or back. My exposed red panty 1/2
covered ass cheeks in the back and a bunch of my bush was escaping around the
sides of my panties in the front and clearly visible through the lace. I was
actually wet ... still wet or again yet to be determined.
We won both matches that day although Drew was much more off his game that
normal. We were scheduled to play our semi final match that night under the
After some dinner we went to the locker room they assigned us to change and
prepare for our night match. It wasn’t too much more than a large single stall
bathroom with an open shower with no door. After giving the room a once over,
Drew said that he would wait outside but I told him it was fine and started to
get ready to shower and change. I said I would go first and told him not to look
as I began stripping down. My knees were actually shaking, my nipples once again
stiff (the cool locker room didn’t help) as I wrapped a towel around my nude
body and walked to the shower.
Since there was no shower door of curtain I have no Idea why I wrapped myself
in a towel. I caught him looking and scolded him but it came across as a joke as
we both laughed and he denied it .....but had no answer as to why I was looking
at his face if he wasn’t looking at me. As I took a shower he stripped and I had
a clear view for the first time of his very large penis. It was semi hard with a
very large head. Its girth and length were much larger than I imagined and
although it was long ..it was extremely thick. . Since there was no shower door
I am sure he got a clear view of my C cup breasts with large dark red nipples,
with tight stomach and firm ass from hours of aerobic and biking and my thick
dark busk that, well let’s just say it is thick but trimmed only enough to wear
I finished my shower and told him it was all his and wrapped the towel around
me to step out of the way so he could get in. He turned the water on and dropped
his towel to reveal a very stiff and fat penis that was now sticking straight up
at the sealing. It caught my full attention and when he saw i was looking he
reminded me of my promise but I told that if he had kept his part of the promise
he would not be in his present situation. In a motherly voice, the best I could
muster at the time, I told him he might want to make the water colder as that
might help. He didn’t laugh but did change the water.
Ok, it was now that I wanted to walk over and join him knowing fully that if
I did I would surely have ended up on my back in the floor at some point with a
teenaged penis thrusting in me .. which actually was appealing to me at this
point. With adult reason, finally, I dried off and dressed but this time I was
really not trying to cover myself and used little modesty. He completed his
shower and dressed still sporting an erection that would have made any woman
blush. He was quiet for a while and eventually the amazing erection he had went
away long enough for us to play a very long match that we eventually won. After
the match I gave him a big hug and a light kiss on his lips rather than the
cheek which I usually did.
We found out that the final wasn’t until the following afternoon since the
other semifinal wouldn’t be played until the next morning and left for the
hotel. The ride was quiet and I was not sure what he was thinking but I was sure
thinking of what I did and what I did to him in the locker room. l broke the
silence but telling him that I should not have stripped in front of my daughters
former boy friend but I just thought that he was old enough to be mature and
this needed to be our secret. He said it was alright with him and he apologized
for what had happened and but when I said nothing happened he referred to his
erection and I told him that it was my fault and at some point and I should have
expected that to happen and any way .. he had nothing to be ashamed of there
either. he looked at me strange but then smiled and said thanks.
We both showered dressed and grabbed a snack when we got back to the hotel
room. I tried to keep it light hearted as possible and reminded him of our
secret when I turned out the light and started getting ready for bed. I asked
for his tee shirt again and slipped it on after I had stripped completely nude.
I felt so horny and so naughty as i slipped into my bed. I couldn’t believe i
had just removed my panties and shorts both and now I could feel the clod sheets
on my bare ass. So what would he say tomorrow if it was my bare ass he saw in
the morning and not lacy panties?
We were talking when I asked him what color were his boxers and he asked me
why and then said that he would tell me if I would tell him what color my were.
I asked him if he liked my lacy red panties and he said they were nice but when
i asked him why, he became quiet for a while, then answered that they were sexy.
I cleared the lump out of my throat and finally got the courage to ask him if he
liked what he saw in the shower this evening or what he saw this morning better.
Once again got quiet before answering “this evening in the locker room but you
also looked nice this morning”. I told him good, liked what I was too.
I reached over and turned the bed side light on which surprised him but what
I did next surprised him more. I got out of bed to reveal that I had a bare ass
and walked towards his bed. From his angle laying in bed, I knew he was looking
right at my uncovered bush. I pulled his tee shirt over my head exposing my nude
body to him and pulled up his covers and slid into bed with him.
Our bodied embraced and I would feel his warm body against mine as we kissed
deep and I held him close. He took over and kissed his way down my neck, ears
and to my breasts which threw me over the edge. He gently rubbed and tweaked one
nipple as he sucked the other making sure he alternated frequently. I removed
his boxers and drove my tongue down his throat as i grabbed his penis for the
first time. He was over 7.5 inches long and so thick I was unable to get my
fingers completely around it. The base of his penis as the thickest part of the
shaft and his balls were large. Even more impressive was the large mushroom
shaped head that, now coated and dripping in precum, was even wider that the
base. My husbands penis was not near this large.
I rolled over on my back and puled him over on top of me and, as I hoped, he
offered no resistance. I had intended to just fuck him but he surprised me again
by starting to kiss my neck and work his way down my body again. After kissing
my ears, neck, shoulders, chest, breasts, nipples, stomach and inner thighs, he
found my dripping wet pussy and clit.
My husband had never gone down on me and, even though I was certain Drew was
not experienced. His lips and tongue traced the lip of my vagina and clit and he
would frequently push his tongue inside of me and run it around the inside of my
vagina before sucking my clit and then starting it all over again. With my hands
on his head, I held him tight and humped his tongue and mouth as my orgasm
neared and I rewarded his efforts with an earth shattering orgasm that rocked
the room and filled his mouth with cum.
He worked his way back to my lips and I told him that it was awesome but we
both soon laughed as he began pulling pussy hair off his tongue and from his
mouth. I apologized but he kissed me deep before responding that I was
beautiful, I tasted great and he liked my sexy hair “down there”. So there I was
... my daughters teenaged boyfriend had just eaten my pussy and given me the
first orgasm I had ever had other than through self masturbation and I was being
told I was beautiful, sexy. He even liked my hairy bush and the taste of my cum.
I continued to taste my cum as we kissed, but I soon needed more and I raised
my knees and reached down to guide his penis to the opening of my very wet
pussy. I had never had such a large dick in my hand as my husbands dick is the
only one I have ever held or fucked and it is shorter and much thinner. He took
over and guided the large head of his penis back and forth across the wet lips
of my vagina mixing my cum and his precum together for the first time, I was on
fire. He slowly pushed and I began to feel the thick head of his penis stretch
me open as he entered me.
His long thick penis was disappearing into my hairy wet pussy and God it felt
good. Our tongues danced together as he began working deeper inside of me and I
soon broke the kiss to tilt my head back and moan as his thick penis began
stretching the lips of my pussy wider and the head of his dick was going so
deep. His breath became shallow and he whispered he was sorry but he wouldn’t
last and began picking up the pace and pushing deeper.
My head was spinning but I told him that I wanted him to cum inside of me,
something that I had never verbally sever said to my husband, and with my hands
on his ass, I pulled him deeper in me. He had his arms around me pulling himself
deeper into me and my heels now firmly dug into his ass .. he let out a low moan
and his penis began to pulse deep inside of me.
The pulses of his large penis were amazing and I too began to orgasm as I
felt a warm douche like feeling as his hot cum began to fill my belly. I had
never felt that feeling and it seriously rocked my world. The amount of cum he
deposited into my totally unprotected pussy was incredible and it wasn’t until
then that I remembered that I wasn’t on birth control but I told myself that I
I had just taken my daughters boyfriends virginity, I had orgasmed on his
face, cum on his incredible dick, had two earth shattering orgasms, had my
unprotected pussy totally filled with his cum and with all probobility just
gotten pregnant. . We lay there for a while motionless until he began to push
his still large 3/4 stiff penis into me again. He raised up on his elbows and
pushed deep and soon the lips of my pussy were surrounding the base of that
giant penis and his large hairy halls were bouncing against my ass. He lasted
longer and began pushing hard and deep causing me to moan.
His cock became fully hard again as it pushed in my extremely wet vagina and
with a few hard thrusts he orgasmed for a second time but this time he was in me
balls deep and the head of his penis was shooting his load directly into my
womb. Pulse after pulse of warm seaman flooded my womb as he moaned in my ear.
We lay in each others arms with the only movement being a sudden spasm of his
penis or the muscles of my vagina as it still gripped his softening manhood. He
eventually pulled out, rolled on his back and we fell asleep with his arms
around me and my head on his shoulder.
The next morning i awoke still in his arms and felt a strange calm and peace
about me. The light of day filled the room and I looked at his in a different
light. I got out of bed and felt his cum begin to run out of me and down my
inner thigh as i went to the bathroom to answer natures morning call. I jumped
in the shower and eventually opened the door to see his naked tight cute ass as
he peed into the toilet. He had a morning woody and looked so sexy for some
reason. I stepped out of the shower and saw him look at me like I had always
wanted to be looked at an our flesh against flesh daylight hug and morning kiss
was amazing. I told him that if we won we might have to stay another night so he
better be thinking about fuzzy yellow tennis balls and not my breasts ..
..well we won and I stuck my tongue down his throat right there in front of
the world and that next night I got a second and third helping of his hot cum
deposited deep in my pussy after coating his dick with my cum from a few earth
shattering orgasms. I loved straddling him and feeling his large penis in me and
his hands on my firm ass pulling me down on him. He said that he always wanted
to feel my ass since he looked at it so much playing tennis and now it was all
He told me how he had masturbated many times thinking about it but when I
asked him about my daughter and third base he said she liked oral (so that is
how he was soo good) and she liked to lick and suck the head of his penis until
he would cum. He said one time she had him cum on the crotch of a pair of my
panties and I wore than the next day. Well, I wear Drew’s cum on my panties a
lot now but that is because if leaks out of me. If my friends knew then I was
fucking Drew they would never speak to me so we just kept it a secret.
My daughter figured it out when she came home and saw her four month pregnant
mom riding her former boyfriends penis on the living room couch. At first he
hated me but now i share Drew and she too is pregnant.
He is a great lover and gives the best kisses and massages I have ever had.
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