OK, I've been very surprised and pleased at the reception my last work has
received.  I've gotten quite a lot of good feedback about my previous story
"Older Cousin."  So much so, that I'm pleased to present the next chapter:
"My Mother's Boyfriend's Roommate."

WARNING: The following story contains man/boy sex.  Do not read further
unless you are over 18 (21 in some areas), are not offended by such
writing, and it is not illegal in your area. Permission granted to store on
the Nifty Archive and to distribute electronically as long as nothing is
charged for it.


OK, my parents were divorced when I was about 9 years old.  I lived with my
mom and when I was about 13-14, she had a fairly serious relationship with
another man.  Well, he was serious anyway.  To be honest, I think my mother
was just in it for the sex.  She was 39 at the time, and her "boyfriend"
was only about 25.  He was in the Air Force, a mechanic I think.  Mom and I
started spending weekends and vacations over at his trailer.

To the best of my memory, he had a cock that was at least 12".  Now, mom's
boyfriend, his name was Tony, never did anything with me, but he didn't
like to wear underwear around the house.  He also had a preference for cut
off jeans which lead to his pecker sticking out of the leg a lot when he
was sitting down.  That's how I know how big is pecker was.

Tony's roommate's name was Len.  He was also in the Air Force.  Tony and my
mom liked to go out and party a lot on Friday and Saturday nights.  Len was
a stay at home type, and he and I got along great right from the start.
Len acted like an older brother.  Since I was the youngest of three, and
the only boy, I really enjoyed having an "older brother."  Mom had no
problems letting me stay with him while she and Tony went out.

After they went out, Len and I would normally sit on the couch and watch
TV, or rent a movie.  I've always been a "touchy/feely" person and even
though the couch was big enough for us to sit without touching each other,
I'd always snuggle up close to Len.  Either he'd put his arm around me, or
I'd put my head in his lap and we'd sit quietly and watch whatever was on
the TV.  To be honest, I didn't think there was anything sexual about it at
the time.  It was just comfortable.  During the commercials or boring
parts, we'd talk or wrestle on the couch.

Len quickly discovered I was very ticklish and soon, that was his favorite
form of attack.  As soon as a commercial came on, he'd pin me to his lap
with one hand and run his fingers up and down my sides while I rolled
helplessly on his lap, back and forth pretending to try and get away.  He'd
stop as soon as the commercial ended, and I'd return to my place next to
him, or put my head back on his lap.  I tried to give as good as I was
getting, but I rarely succeeded. He was older and stronger than me.
Whenever I tried to get even, he'd just hold me down and start tickling me.

I was only able to get him back with Tony's help.  We would gang up on Len
and while Tony held him down, I'd tickle him until he couldn't see
straight.  Once I even ticked him until he lost control and started peeing
on himself.  Of course, he got revenge that night.  While he didn't make me
lose control, he did tickle me on and off (more on) for the entire movie
"Dune," the long version, 2.5 hours.  He only stopped when I was gasping
for breath.  He'd allow me to rest for about 2-3 minutes then start again.
You can bet, I never tickled Len to that point again.

I did get even for the extended tickle attack thou.  The next day, Mom,
Tony, Len, two or three neighbors and myself were all playing Trivial
Pursuit.  The adults were in chairs and on the couch while I was laying on
the floor.  Len had to step over me on his way to this kitchen to get a
drink.  On his way back, I reached up, snagged his shorts and pulled them
down around his knees.  Len wasn't wearing any underwear and ended up
flashing everyone present.  It took him a few seconds to realize what I had
done and then he practically jumped into his seat and hid his crotch with
his hands.  I've never seen anyone turn as deep a red as he did that night.

Our relationship changed shortly after that.  One of Tony and Len's friends
was getting out of the Air Force and they decided to have a big party for
him.  On the night of the party, Mom "banished" me to Len's room along with
a TV and my Atari.  I was supposed to stay in the room, play video games,
and in general, keep quiet and not disturb the party.  One look at the
guests, and I didn't want to be around them anyway.  Mom was afraid that
once they got drunk, I would hear and see things I shouldn't be hearing and
seeing.  I was happy to stay in the room and play Space Invaders.

I stayed up until about 11:00 reading comic books and playing with the
Atari.  I normally slept on the couch in the living room, but since there
was a party going on in there, I stripped down to my briefs and climbed in
to Len's bed (I'd been sleeping in my underwear ever since I was 9 or so).
Some time during the night, I felt the covers pulled back and heard Len
tell me to scoot over so he could get in the bed.  Len only had a full
sized mattress but I figured we could both be comfortable.  Once he was
settled, I moved close, snuggled up to him, back to front (his front, to my
back) and went back to sleep.

I woke up in the middle of the night and we were still in the same
position, but Len's arm was wrapped around me.  I moved his arm, got up,
used the bathroom and then started to climb back in bed.  It was then that
I noticed Len wasn't wearing anything.  Well, since I was at the age where
I wanted to seem "grown up" I quickly pulled off my underwear, crawled back
in bed and resumed my position.  Len woke up enough to drape his arm around
me again then fell back asleep.  I squirmed against him until I found a
comfortable position and joined him.

I woke up again, sometime before dawn when Len threw the covers off,
shifted his weight and got out of bed.  I heard him in use the toilet and
then come back in the room.  I was still laying there, pretending to be
asleep hoping he'd hurry up and get back in bed (I was getting cold with
the covers thrown off and my rear end exposed like it was).  I heard Len
standing there, breathing, and then finally he got back in bed.  He tossed
and turned, trying to find a comfortable way to lay down, without
disturbing me and finally, he had to return to the positions we were in
before he got up.  However, he didn't press himself tightly against me this
time and I was still cold.  I sleepily reached behind me blindly and
searched for his hand.  I brushed against his chest and then traveled down
until I hit his crotch.  At that point, he put his hand in mine (presumably
to stop my searching) and I pulled his arm back over me.  This forced him
to scoot over against me again.  We ended up i!  n the same position, but
this time I felt something poking me in my butt.  I didn't think much about
it and started to go to sleep again.

This time, however, Len was awake (and sober) enough to realize where his
cock was.  He also knew where his hand was.  Instead of going back to
sleep, Len started rubbing his hand across my nipples.  The contact
thrilled me, but I forced myself to pretend to be asleep.  Len slowly
caressed each nipple, then moved his hand down my body.  I was almost
shaking with pleasure when his fingers reached my crotch.

Despite my best efforts, I let out a gasp when his hand wrapped around my
cock and started slowly pumping.  When he heard my gasp, he quickly removed
his hand and started pulling away from me.  I caught his hand with mine and
guided him back to my penis.  He leaned into me and whispered in my
ear. "Are you sure you want this?".  I answered him by groaning and pumping
my hips so my cock thrust in and out of his fingers.

The pumping had an added effect of slipping his hard cock up and down my
crack.  He pushed forward at the same time I was pumping back and we
managed (I think totally by accident) with the tip of his cock pressing
against my butt hole.  He groaned and started fisting my cock faster and I
felt something wet and slippery seep from the end of his dick.  He met my
next push with one of his own and I felt is cock slip into my virgin ass.
I froze and started whimpering as I felt the strange sensation of his cock
inside me.

Len groaned and started pumping my cock.  At the same time he started
pushing against me steadily.  I was so intoxicated with the pleasure his
hand was providing me, I didn't notice his cock was sinking deeper and
deeper into me until I felt his wiry pubic hairs mash against my butt.
Once in, he paused for me to get used to his cock in my rear and asked me
if I was doing OK.  I told him it felt strange.  He asked me if it hurt,
and I replied that it did a little at first, but now I just felt full, like
I needed to use the bathroom.  Len replied that it would feel a lot better
in a few moments and started to slowly pull his cock out.  When only the
tip of is cock was left in me, he reversed direction and started pushing it
back in.  All the while he was working my cock like a pro.

Len continued his slow fuck for the next 10 to 15 minutes.  Slowly easing
his cock in and out of my ass.  All the while he kept stroking my cock and
whispering in my ear how about how good it felt, and how hot/tight my ass
was.  After about the first 2 minutes of this, the "full" feeling
disappeared and my ass started feeling warm.  At the 5 minute mark, it
started feeling HOT, and by 10 minutes, I was gasping for breath and
silently begging him to fuck me harder.  All the while, Len kept pounding
my dick and running his hands all over my body.

After about 15 minutes of this, I could take no more.  My cock grew steel
hard in his hand and I launched into the biggest, most intense orgasm of my
life. It seemed like I came forever.  I even think I passed out as my
senses were overloaded.  When I returned to conscious Len was still
pounding away at my ass, and my cock was still rock hard.  He was pumping
faster, and harder.  He was taking short fast strokes.  It only took about
1 to 2 more minutes before he blasted his load up my ass.  The instant his
hot cum started burning my ass, I came again.  Not a powerful, or as mind
blowing as the last time, but still it was very pleasurable and completely
relaxing.  As Len finished his orgasm and his cock shrank, we both slipped
back to sleep.  My last memory of that night was his cock, now semi-soft
slipping from my stretched hole.

I awoke the next morning to find Len still snuggled up against me, in the
same "spoons" position we were in the night before.  I felt his cock
pressing against my ass, but it wasn't hard.  I ran my hand down, over my
ass and stuck a finger inside.  I felt the remains of last nights encounter
and sprung an immediate erection.  I reached over and started playing with
Len's cock.  I was trying to wake him up and get him hard at the same time.
His cock came up before he woke up and ever the eager beaver, I quickly
backed up to him and inserted his cock up my ass.

Unfortunately, I went to fast and instead of the pleasure I felt last
night, my ass felt like it was being torn open.  I was unable to keep
myself from crying out, and I jerked my ass off his cock.  I was quietly
sobbing and rubbing my ass when I felt Len's hand pull me to him.  He
reached around and started rubbing my cock and quietly whispered into my
ear "Next time, wait for me and it won't hurt.  I'd never do anything to
hurt you."

I turned over and looked at him.  He was grinning from ear to ear.  He
hugged me and then told me that we didn't have time to do anything that
morning and that I should probably let my ass rest for a bit anyway.  We
both got out of bed and I pulled on my briefs and he pulled on a pair of
sweat pants.  I went to the kitchen while he went to the bathroom to take a
shower.

When I got to the kitchen Mom made me big bowl of cereal.  When Len came
out of the shower, and walked into the kitchen, Mom asked him if I was a
"good boy" last night.  He winked at me, and told her that squirmed around
a lot, but other than that I was OK.



What happened after:

Mom and Tony never did figure out what Len and I were doing.  Every time
they would go out, Len and I would go back to his room and he would screw
me.  He was always kind and considerate.  However, he never did let me do
him, and to be honest, the thought didn't occur to me.  Len always gave me
a "reach around" and never came before I did.  We didn't kiss much, but we
did hug a lot.  I never slept in his bed unless there was a party but when
I did, Len often left the party early and spent the night with me, holding
me, loving me, and making love to me.

Len got out of the Air Force about 8 months later.  He moved back home to
Ohio and I never saw him again.  He did call four or five times, but since
Mom was always around, we couldn't really say much.

If you enjoyed this story, please e-mail me at cn1458@coastalnet.com.  As
always, comments, and suggestions are welcome and will get you a reply.
Flames will be deleted.

If you enjoyed this story and want to read more about my life, let me know.
I still haven't told you about my experiences with: the friend Len set me
up with when he got out, my grandfather, my uncle, my other uncle, the high
school principal, and others too numerous to think about right now...

Again, you can contact me via email at cn1458@coastalnet.com.  Suggestions
and critiques will be replied to, Flames will be deleted.