Date: Thu, 5 Jun 2014 11:48:33 -0700 (PDT)
From: Mountain Bottom <mountainbottom@yahoo.com>
Subject: Losing My Cherry At His Lakehouse

Losing My Cherry At His Lakehouse
	
	The following is a true story of the first time I had sex with a
man. I was a sophmore in college in a small mountain town west of
Burlington, Vermont in Upstate New York when this story took place.
	
	My name is Matt. I had known I was interested in gay sex since I
was around 12 or 13 years old. Using the internet I found out about how men
could get each other off. I was specifically facinated with the idea of
anal sex and knew pretty much straight away that I was a bottom. Using what
I had learned on the internet I soon started to spread my skinny legs while
in bed and play with my hole while I was exploring the art of masturbation.
Again through the internet, I found out about using lube (I just used some
moisturizer) to make the whole experience more pleasurable. I started
finger banging myself while I was jerking off. I was developing a strong
passion for anal play!
	
	As time went on I began to fantasize more and more about actually
being fucked by another man. I was able to fit more fingers in me and had
moved on to other objects such as sharpies, small cucumbers, carrots. Cigar
tubes make real nice makeshift dildos! I was developing deep fanatasies
about sucking a guy until he was hard and then letting him absolutely pound
my little hole. I was always on the skinnier side. At the time that this
story took place I was 5'11" and just 140 pounds. I have blond hair and
blue eyes and not a lot of hair on my body, just a little on my legs and
arms. Basically, I have what is considered to be a cute all american face
and a tight body.
	
	Even though I was aching to be fucked by a man, I had never managed
to act on that desire. Mostly because I was nervous and not out of the
closet so I was never in a social environment where it would just happen. I
had been on online hook up websites but was always reticent about actually
meeting up with the guys I had met on there. Eventually I left my hometown
in the city and went to a small college in the mountains. There was
absolutely no way I was going to be finding much gay action there and I
spent my freshman year partying and making good friends without even really
thinking about how to finally lose my anal cherry.
	
	The summer after my freshman year I took a summer job in a kitchen.
I worked pretty hard during the week and took it easy during the weekend. I
managed to land a pretty cheap one bedroom apartment and spent the evenings
and weekends hanging out with friends or by myself resting. It was during
this time that I really started to think about getting fucked again. I had
made some money and had a space to myself so after a night of drunken
masturbation to twink bottoms getting fucked and cruising personal ads I
bought some anal toys online. I got some anal beads, a vibrating anal
probe, and a lifelike dildo with a suction cup base. The dildo was a pretty
good size for me at the time. It was about 7.5" long and not too thick,
about 2.5".
	
	I would lay out a towel on my bed and watch myself in my full
length mirror as I played with my shaved and cleaned hole. I would pop each
anal bead in slowly and pull it out at a measured pace while jerking off to
the sight of my hole slowly expanding and contracting around each bead. I
would probe as deep as I could get the probe while the vibrator would shake
my innards. The dildo was my favorite though. I would put the suction cup
on the ground and usually start off by riding it, looking at myself in my
full length mirror and trying to look as sexy as possible while fucking
myself on it. I would then attach it to the head board and fuck myself
doggy style before laying back on the bed and slamming myself while jerking
myself to orgasm and covering my stomach and sometimes my face with cum
from the intenity of the orgasm.
	
	Eventually I realized I wanted a little something more. I thought
about buying more or bigger toys but realized what I really wanted was to
be fucked by a man. I couldn't take it any longer, I really need to lose my
anal cherry! I started to get serious about cruising profiles online
looking for the right kind of guy to hook up with. I quickly exhausted the
local options and decided I might need to travel a little bit to find what
I was looking for. I am generally into older guys around 40 years old who
are a little bigger than me and in good shape. I have to admit I was also
looking for someone with a dick that was bigger than the dildo I had been
using. I wanted my ass to be stretched!
	
	One night I was cruising the personals of Burlington, Vermont when
I found Ben. He was in his mid-40s, 6'2", with short salt and pepper hair
and in absolutely amazing shape with strong arms, nice pecs, and tight abs
with a little hair on him but not super thick. He had an extremely handsome
clean chaven face and a very confident air about him that was very
attractive. His profile stated that he was a total top looking to hook up
with a young eager bottom in his early to late 20's, possibly making it a
regular thing. He listed his cock size a being 8.5" and 3" thick. He said
he was into really making love to his bottoms and that he was more than
happy to accomodate those that are inexperienced. He also said that he
could host the encounter. I was sold! I sent him a message telling him how
interested I was and that I was interested in talking to see if we might be
a match. I even told him I was looking to lose my cherry to someone. I
unlocked my face pictures and the rest of my body pictures that showed me
on all fours among other positions.
	
	After a week with no response from Ben I had given up on him. I was
a little disappointed but knew that was the nature of these online hook up
sites. I had already continued my search. It was the beginning of the week,
a Monday or Teusday, and I was online looking at porn and cruising hook up
sites when I got a new message. It was from Ben! He said he was sorry to be
so late but he had been on a business trip to Japan. I was super
impressed. He was wondering if I was still interested. He said he love my
pictures. He also unlocked a picture of his dick and a couple pictures of
him fully naked. They did not disappoint. His dick made me drool just
looking at it. I was actually wondering if he had been a little modest in
his measurements on his profile. He was circumsized and it looked so cut
and muscular with a big fat shiny head on it. My asshole twitched just
looking at it. Of course I was interested! I sent him a message immediately
saying so.
	
	He got back to me shortly with a phone number, saying I should call
him if I wanted to set something up. This man was absolutely no nonsense. I
didn't know what to do. My heart was racing, I was pacing around. I was a
wreck. I didn't think it would be this quick. A half hour ago I was jerking
off wondering if I would have to travel 4 hours to Albany to get fucked and
here I was with a phone number to call. I made myself a strong drink to
calm down. I took a couple sips and decided this was it, I had to take the
plunge at some point. A little calmer now, I dialed the number for Ben and
pressed send. It started ringing and rang 3 or 4 times. I thought he wasn't
going to pick up!
	
	"Hello?", came the voice on the other end.
	
	"Oh hi!", my voice squeeked. "This is Matt, we were just talking
online?"
	
	"Oh hi Matt!", said Ben. His voice was warm and soft. From the five
words he had said he sounded kind but confident. So silly how we pick up on
these things!
	
	I was extremely nervous but the manner with which Ben spoke calmed
me soon enough. We talked about how we were doing before getting down to
business so to speak.
	
	"So you have never had sex with a guy before?", he said.
	
	"I actually haven't", I said, a little nervous again.
	
	"Well, don't worry, we could go as slow or as fast as you'd like. I
can be very accomodating. I think you will find it very comfortable here
and I think we can have a lot of fun."
	
	He asked if I was free that next weekend and told him I was. He
said I could get their on Friday in the late afternoon and I could stay the
night if I wanted to afterwards. I said that sounded nice. I asked him if I
need to bring anything. He laughed and said he had everything we would
need. Maybe bring a toothbrush. I laughed at that. I was wondering what
kind of place I was going to. I told him I would call him when I was
leaving. He said that sounded great. We both said how much we were looking
forward to it, said goodbye, and hung up.
	
	I was so turned on. I basically jerked off in 2 minutes while
looking at his picture fantasizing about how it was going to be. I honestly
couldn't wait. The next couple days went excrutiatingly slow. All I could
think about was my meeting with Ben. I basically had a 3 day hard on! I
wouldn't let myself jerk off. I wanted to have a truly explosive orgasm
when the time came.
	
	Eventually that Friday came. I was so excited. I managed to get
through work. I got out around 1:30 (I worked morning shift). I went home
and jumped in the shower. I cleaned my self super well. I carefully shaved
my balls, dick, and asshole. I douched myself thouroughly and I was ready
to go! Of course my bags had already been packed.
	
	I called Ben to tell him I was on my way. His warm voice answered
the phone. He said he couldn't wait and gave me his address. The address he
gave me was on a pretty exclusive island just north of Burlington,
Vermont. I expressed my excitement and he said how much fun we would
have. We said our goodbyes and hung up.
	
	I was on my way. I don't remember much of the drive there. I
followed the directions I had printed out absentmindedly. It seemed like it
took forever, even though it took only a couple hours or so. Eventually I
got the ferry that brings you across Lake Champlain to the island that Ben
lives on. When I started driving toward the direction of his house, I
noticed that the houses were beuatiful and huge! Eventually I realized I
was just about there. I saw the number for his house which was actually on
a gate. The gate was open and I drove through and started down a long
driveway which sloped down toward the lake. I came to the house of the
property after emerging through a small stand of trees. I couldn't believe
this place! It was beautiful. I'm no architecture expert but it was a
modern house with plenty of windows and wide open spaces visible from the
parking area. Outside was a BMW and I could see Ben inside tidying up a
couple things. I parked the car, grabbed my small bag, and started towards
the door. Ben had noticed me driving up and opened the door before I got
there. We both had absolutely huge grins on our faces.
	
	"Hi Matt!", He said with that warm voice I recognized on the phone.
	
	'Hi Ben!", I said maybe a little more meekly. "It's nice to meet
you."
	
	"You too!", he said. "Welcome to my home."
	
	I stepped inside with him, his hand on my lower back, which sent a
shiver of anticipation through my body. He was exactly as I thought he
would be from his profile and picture. Apparently they were pretty up to
date. He moved through the house with a sexy confidence. He gave me a brief
tour, ending with the bedroom, where he flashed me a brief smile as he
introduced it. We both knew what would be happening there! His house was
amazing. He told me he was an antique dealer, which is why he had been in
Japan.
	
	We went back to the kitchen and Ben offered to make us drinks,
which I gladly accepted. We went out onto his porch and sat on a very
comfortable outdoor couch next to each other. We were both wearing pretty
thin shorts and t-shirts as it was in the mid 80s temperature wise. We
talked about ourselves a little, where we were from etc. As time went by
Ben had been stroking my shoulders a little and I put my hand on his leg
flirtingly. We were laughing a little and getting on great.
	
	At some point the conversation died down a little and the stroking
and touching got a little more serious. We had both had a couple drinks by
now and were feeling pretty good.
	
	Ben said, "So, you've really never had sex with a guy before?"
	
	"I haven't." I said, with a smile.
	
	"Have you kissed a guy before?", Ben asked.
	
	"I have done that.", I said, which was true, but it was in high
school during a drunken after party for a play I had been in.
	
	"Would you mind if I kissed you then?", Ben asked with his sexy
voice.
	
	"Of course not", I said with my hand rubbing up and down his leg by
now.
	
	Both of us had noticable bulges growing in our pants. Ben leaned in
a kissed me on the lips. He had soft lips and it felt amazing. A bolt of
electricity carried through my body and my cock moved in my shorts. We
proceeded to make out for while with our hands exploring each others
clothed bodies. I made the first move to disrobe him, taking off his shirt
and revealing his toned, slightly hair pecs. They glistened with a faint
sheen of sweat. He smelled wonderfully of just the right amount of cologne
and aftershave. My dick was rock hard by this point and I could tell from
the tent in his pants that he was too.
	
	I wanted to tease hime a little though. I rubbed my hands all over
his chest and abs and continued to make out with him. He took off my shirt
and did the same thing. Eventually I moved away from his face and started
to kiss down his neck to his pecs, where I kissed and sucked on his
nipples. He threw his head back in pleasure and allowed me to slowly move
my way down to his abs. I got up then and took off my shorts making myself
completely nude for him to see.
	
	"Wow", Ben said. "You are Sexy".
	
	I just smiled and helped him unbutton and take down his shorts
while he stayed seated. I threw them into my pile of clothes next to the
couch. When I went back to him I admired his naked body. He really was in
great shape. Of course what really got my attention was his dick! It was
hefty! Well muscled and cut as I had seen earlier in his online picture,
but that did not do it justice. It was a powerful tool, I could tell. The
head was massive and enflamed with blood at the moment. I just couldn't
wait to get a taste.
	
	I went down on my knees and looked at him in the eyes from my
crouched position before him. He nodded his approval. I started back on his
abs and kissed down towards his crotch. I kissed around his legs and then
moved up to his balls. I hadn't really noticed them with all the attention
I'd paid to his shaft, but they were beautiful as well. Nice, plump, and
shaved. They were drawn tightly up to his erect shaft. I slowly licked each
one and then took them into my mouth. It was the first time I had tasted
part of another man's manhood and I was hooked, just like I knew I would
be. I was overwhemed by the smell his musk and how clean he was. He had
clearly washed himself well just like I had. I was intoxicated by it.
	
	I then turned my attention to his raging shaft. I grabbed it and
inspected it before slowly licking my way up his expansive underbelly
before stopping just short of his head. Ben moaned loudly at this point.
	
	"That feels so good! Are you sure you've never done this?", he
said.
	
	I smiled broadly. "I swear I haven't".
	
	I then returned to his shaft licking all around the base and up,
exploring every aspect of his huge cock but the head. Eventually once his
dick was completely soaked by my saliva I licked up the underbelly once
again and continued up the head to the tip of his cock. I flicked my tongue
across his slit, licked around the entire head, before taking the whole
thing into my mouth. I couldn't believe how much of my mouth it took up. I
was a pretty big head. Not one of those dick heads you see in pornos that
are just way too much to deal with but impressive none the less.
	
	I proceeded to give him a nice long blow job with him, moaning,
encouraging me, and giving me tips to please him even more. Being quite a
novice I was not able to deepthroat him at all but I could tell he was
happy with the job I was doing. I couldn't believe how satisfying it was to
have a fat cock in your mouth. I went back down to his balls and also used
my hands to please him. This must have lasted at least half an hour but to
be honest I lost complete track of time.
	
	Eventually I pulled off his soaking wet dick to get my breath and
he used that opportunity to ask if I wanted to go inside. Of course I was
more than happy to knowing that we would most likely be moving on to other
sex acts when we were there. I walked inside in front of Ben. He put his
hand on my ass and guided me toward to bedroom. Once inside he put on some
dim mood lighting in the corners and told me to wait a second before
getting on the bed. He then lay down and told me to straddle him on my
knees with my face at his cock and my ass and cock over his face. He didn't
touch my cock, which to be honest I was fine with. Instead, as I started to
go down on him again, he opened a drawer next to his bed and pulled out a
bottle of lube. I couldn't believe a man was finally going to play with my
ass!
	
	Ben lubed up one of his fingers and asked, "Are you ready for this,
Matt?".
	
	I moaned my consent, let his dick fall from my mouth and said, "Of
course I am!".
	
	Ben then rub a liberal amount lube on the outside of my hole. He
slowly started working his finger in. "Nice and tight. I love it", he
said. I allowed myself to relax back there. I remembered everything I had
learned from reading on the internet and playing with myself. I pushed out
a little like I had to go to the bathroom and this allowed hime to quickly
start finger fucking me. I definitely wanted more than one finger though
and Ben quickly started adding more fingers. Before we knew it he had three
of his musclular fingers sliding in and out of my ass as I continued to
play with his sizable dick and balls.
	
	Then he said what I had been waiting to hear for almost a decade.
	
	"Do you think you want to try taking my dick now, Matt?".
	
	Did I ever!? I coyly said, "I think so, Ben".
	
	He said, "We can go nice and slow. Let me know if anything hurts or
is uncomfortable. I think it would be best if we started with you sitting
on it. That way you can control the pace."
	
	I dismounted from my position and knelt next to him. Ben took a
condom from the drawer and gave it to me. "Would you like to do the
honors?".
	
	I opened the packet and slowly unrolled the condom down his sopping
wet cock, thinking about how I had just had that monster in my mouth. He
grabbed the lube and poured a liberal amount onto his condom covered dick
and said, "You ready?".
	
	My heart was beating so fast. I couldn't believe I was about to get
fucked and I couldn't wait for it. "I'm ready", I said.
	
	I stood up and positioned myself directly over his dick, which he
was holding steady sticking straight up. I knew this wouldn't be easy but I
was hoping my practice with my toys would pay off. As I crouched, I took
his dick from him and positioned it right at my hole. I pushed out with my
ass muscles and felt that the tip of his head was right at space between my
puffy ass lips. I allowed myself to lower myself slowly onto the head and
felt his cock head gradually spread my lips and gain access to my ass. It
got to the point where I really needed to apply some pressure to continue
and I let myself push down a little more and a little more until the entire
head popped into my asshole. A wave of fullness and just a slight bit of
pain coursed through my body. I gasped.
	
	Ben moaned and looked at me in the eyes. "Are you ok?", he said.
	
	I nodded and smiled a little. "I'm great! It feels so good". I was
breathing heavily and allowed myself to take a little break crouching with
Ben's dick head stuck in my ass. My toy practice was definitely helping me
take this.  After 30 seconds or so I slowly continued to lower myself onto
his massive dick. It slowly got wider until the middle of the shaft so my
hole was getting stretched further and further. At this point, his dick
reached the second sphincter allowing access to my colon. I went up and
down several times allowing myself to get used to the size his his dick in
the part of my ass it had reached so far. Ben had his head back and was
moaning and telling me how good it felt much like when I had been giving
him head outside. I was supporting myself by holding on to his muscled
pecs.
	
	After fucking myself with part of his cock and letting my asshole
get used to his size, it was time to try and break through the second
sphincter and take the rest of him. I really let gravity take over and let
his cock press deep inside of me me. I pushed out like I really had to go
to the bathroom. I then felt my inner sphincter release and Ben's dick slid
almost all the way in side me. Talk about feeling full! I couldn't believe
how good it felt. I moaned deeply and said, "Oh my fucking god that feels
good." A warm feeling traveled through my entire body and I sat there
appreciating the feeling of having a hot, fat dick filling my ass. Ben
pulled me to him and we kissed long and deep. As we were kissing, for the
first time he started to slowly move his hips up and down, fucking me
gently and slowly. I could feel every vein in his meaty dick as it slid
passed my o-ring.
	
	I was really feeling the pleasure now. I told Ben he could fuck me
faster and harder. He responded by picking up the pace and grabbing hold of
my ass cheecks, spreading them. At this point the last little bit of his
dick slid into me and reached a part of my ass that had never been reached
before. I moaned so loudly and Ben said, "Does that feel good, baby?". I
couldn't believe how turned on I was to be referred to so affectionately
and started meeting his thrusts even harder, our bodies smacking together
with each plunge into the depths of my body.
	
	I decided I wanted him to fuck me in another position. I raised off
him and his dick popped from what I was sure was my now red and open
hole. I asked him how he wanted to fuck me.
	
	He said, "Do you want to try doggy style?"
	
	I didn't even say yes. I just got on all fours and presented my ass
to him and smiled at him. He laughed and lined his dick up with my asshole.
	
	"From here it looks like you are ready to be fucked", He said. I
was pushing out my hole and he said, "It looks like you are gasping for
cock".
	
	I smiled even wider and said, "I am!"
 	
	With that he pushed his dick into my asshole with a slight pop
again as is massive head invaded my ass. He slowly pushed inward until his
ball were resting on my ass. He pulled out until the head, grabbed the lube
and slowly pushed in while dribbling lube along the length of his shaft.
	
	"Are ready to really be fucked by a man?", he said.
	
	"Yes. Please fuck me so hard!". I exclaimed, pushing my ass back to
meet him.
	
	Then he really let loose. We were both really moaning and being
very vocal at this point. I kept telling him to fuck me hard and take my
asshole. He kept telling me what a nice ass I had. He was running his hands
up and down my back and holding my waist and then my ass. But the feeling,
I my god the feeling of really being fucked by a man. With every thrust
electricity emanating from my well strech ass lips spread through my
body. The feeling of our sweaty bodies smacking together at the same point
that he reached the deepest part of the inside of his body that he could
reach. was just incredible. He kept fucking me doggy style for a while. The
talk kind of slowed down while we settled into the ecstacy of sex. My mouth
hung open while I enjoyed the feeling of having my ass plundered.
	
	He slowed down eventually and pulled himself all the way into to
me. Hugging me, he maneuvered us so that I was on my side as was he behind
me with one of my legs up and one flat on the bed. He continued his
thrusting then, hitting a different part of my insides. It felt amazing! I
fel like I was being penetrated in a completely different hole for a
minute. In this position I could also turn and make out with him while we
fucked. We continued to fuck like that as he pinched my nipples and rubbed
his hand on my flat belly as if to try and feel where his cock was fucking
me. I felt like could come at any second at this point if I had grabbed
hold of my dick, but I let it flail around during the fuck.
	
	He then slowly withdrew his dick from his ass. I looked at him with
slight disappointment in my eyes.
	
	He laughed and said, "Wow. You really do like being fucked, don't
you".
	
	I laughed back and just said, "MMMHHMMM!".
	He laughed again and with a smile pushed my legs to each side of me
and back. He grabbed a pillow and put it under my ass, raising it off the
bed. He then placed his big dick against my ass lips and sank his cock in
all the way with one firm but gentle thrust. I let out a huge moan.
	
	"I want you to jerk off while I fuck you missionary style and then
I am going to cum right after you do. Does that sound good?"
	
	"Yes! That sounds great", I said without hesitation.
	
	"Where do you want it?", he asked.
	
	"In my mouth?", I said cautiously with a smile.
	
	He laughed and said, "I'm gonna cum in your mouth then!", and
continued his thrusting.
	
	I was back into a world of ecstacy as he fucked me, getting really,
really deep in this position. My dick which had been only half hard as I
had been focusing on the feeling in my ass slowly came to full mast as I
played with it. Between the feeling of his huge dick spreading my inside
and ass lips and the fact that I had not jerked off in several days it took
almost no time before I exclaimed that I was gonna cum.
	
	And cum I did! I let loose the biggest orgasm of my entire life. I
shot cum all the way up my body, over my head, into my hair, on my face and
all over my belly and chest as my body shook with overwhelming
pleasure. Ben's huge dick was still in my ass being squeezed by the
contractions of my body.
	
	Ben laughed and quickly pulled out as the last dribbles of cum
dripped from my still hard dick. He quickly pulled the condom off, moved
right next to my head, and masturabted his dick which was slick with lube
and sweat from being in the condom. He placed the head right at my lips so
all I had to do was slightly close my lips around it as he gave it a couple
final strokes. He then moaned and threw his head backwards as I could see
his balls tighten up and his shaft pulse.
	
	I felt my first splash of another man's cum hit my tongue. The
overwhelming scent of his manhood filled my olfactory system. The funky,
salty, yet incredibly intoxicating and delicious taste filled my mouth. I
decided not to swallow right away but to let him fill up my mouth so I
could savor the feeling and flavor. He came so much though that I had no
choice but to start swallowing his cum or it would have started dribbling
out and I certainly didn't want to lose any! As each spurt hit with intense
velocity I swallowed a little bit until he ran dry.
	
	Ben flopped down beside me on the bed, spent. I swished his cum
around my mouth, savoring the flavor as if I would never taste it again.
Which at that moment I knew not to be true. I was officially a gay sex
junky after this experience. I swallowed Ben's cum and then moved over to
rest on his heaving chest. He put his arm around me and sighed with
satisfaction.
	
	"So, do you want to stay the weekend?", he asked, smiling.
	
	We both laughed and I gave him a big kiss.