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.