First Time with a Man
I was mid thirties or so and still in a sexless marriage. By this time, I had had a couple of experiences with guys I met at an adult bookstore nearby. My sexual experiences with guys started out with me being a bit of an exhibitionist in a video booth with a couple of glory holes. I would show off and I had a couple of mutual blow job exchanges. But I wanted more.I loved being naked in the booth. When I was in the booth, I would watch straight threesomes, you know, with the girl getting it in both ends, and while I was giving head, I began to fantasise what it would be like to have a man inside me. When I masturbated at home, I began to finger my ass, then I started to lube my ass, trying to insert as many fingers as I could. But it never seemed to be enough.I don't remember exactly how, but I think a coworker mentioned to me that they had bought something off craigslist. I checked it out and it didn't take long for me to find the adult personals section. I found the m2m personals and I began to check them out. Then I began to respond, but it seemed that guys looking to bottom always outnumbered the tops. I chatted with a few guys, but without any success.I had to do a trip for work. I would have to travel to the next province and I could have gone by car or plane. Just for the heck of it, I checked out some of the craigslist posts for cities along the way. I found one with an older top looking for a bottom. Not many of those, so I replied. He got back to me right away and after a few emails back and forth, he asked if I wanted to hook up. I was nervous. I made a plan. If I drove, and left the jobsite late, then I wouldn't make it back home til 2 or 3 in the morning and the wife would be fast asleep. I wrote back and gave him the date and time that I would be passing though. I thought it might be too late, but he said yes and he gave me directions to his house.I have to tell you, I was already feeling tingly, nervous, but good nervous, and my ass area began to get tingly too.On the planned night, I stayed late to be sure that I wouldn't arrive at his place until late at night. The drive was torture. I was nervous with anticipation. My ass tingled (it really does when I get horny and am going to bottom), my cock was rock hard for most of the trip and I stroked it liberally whenever there was no traffic. I didn't cum, though. I was saving my cum for later.At last I arrived at the fork in the road. I could chicken out and go straight back home, or I could turn off and head to his house for my first real full contact man to man experience. I turned off.It was late, after midnight and the night was hot and misty. I followed his directions to a little town and an old farm house with a big wrap around veranda. He told me to pull around back - nosy neighbors he said. So I followed the overgrown gravel drive to the back of the house. When I stepped out of the car, I felt hot. The moist air made me instantly sweaty. My stomach was all butterflies, and my ass, well you know, it seemed to be tingling in anticipation. The hole area from the base of my balls back along my crack and the inner parts of my ass cheeks was hot. It was as if it was waiting for some kind of release.I went to the door and knocked.An older man came to the door. He was as he said, late fifties, maybe 60, maybe 5"11 or 6' - a couple of inches taller than me and quite a bit heavier. Not really heavy, it's just that I was only about 150 pounds, and he probably 180 or more. He had a kind face with a little scruff, salt and pepper hair. Just as he described. In our online chats he said he had 7" and I was hoping it was true.He showed me into his living room. He said it was the old family home. He lived in Ontario now, a teacher, but he came back here for the summers. His wife had left the week before to head back home and he stayed behind to close up. He disappeared into the kitchen, and came back with a bottle of wine and two glasses. I have to tell you, my hand was shaking when I took the glass. I took a long drink. Liquid courage. I was really nervous. He noticed and refilled. We sat for a bit chatting, he on one couch and me on the loveseat facing him. I finished my glass. He got up to refill it, and when he sat down, he sat next to me.I took another long drink and let the warm wine glow wash over me. I smiled. I was starting to feel comfortable. He got closer and began to run his hand along my thigh as we chatted. I began to get hard again and soon enough, his hand began to rub over my stiffening cock. He was very close. I looked deeply into his eyes and then he pressed forward and began to kiss me like a man kisses a woman. Even though in the back of my mind, I knew it would have to come to this, it was still a bit of a shock and I instinctively pulled away up against the arm of the love seat. He persisted and all I had done was lie back, making it easier for him to get over me. I relented. Afterall, I wanted to bottom. I was going to be the woman. I gave in and it was such a relief.He continued to kiss me and I kissed him back. He got my shirt unbuttoned and ran his hands over me, over my chest, my belly and down over the bulge in my jeans.Then he stopped and stood up. "Let's go to the bedroom," he said. I was a little tipsy, maybe I had more than I thought. and I was also unbelievably horny.He took my hand and we climbed the stairs. He showed me to the bathroom."You probably want to clean up and clean out." He pointed to the shower and to a douche bottle on the counter. Then he left me and went down the hall to the bedroom.I entered and closed the door behind me. Slowly, I stripped off. I took the little bottle. It was already full. I got in the shower and turned it to hot. I washed and used a face cloth to make sure all my privates were clean, front and back. Then, I soaped a bit and slid a finder into my ass. My cock jerked. I moved it in and out to try to loosen it up a bit. Then I had two fingers in. Finally, I used the bottle. I had never really thought about bottoming, you know, the mechanics of it. He showed me a douche bottle and I knew that I was supposed to clean out so a few times with the bottle and a few trips to the toilet and I was readyl.When I was all clean and dried off, I put my underwear and shirt back on, unbuttoned, and then I walked down the hall.He was laying on the big brass bed in a white robe. HIs robe was open at the top and I could see a nice hairy chest with a little bit of grey. He motioned me over.I stopped before him and he said "turn around and drop your shirt."I turned around and let my shirt drop slowly to the floor. Then I felt his strong hands on my ass. Gently at first, just sliding over the fabric of my briefs."God you have a nice round ass." He said. Then one of his hands was on my cock, rubbing it though the fabric. "And I can feel a nice package." Then I felt his other hand venture along my ass crack. I instinctively spread my legs a little and he rubbed over my hole and along my crack. I let out a huge sigh, it felt good. My ass was alive, on fire, waiting, anticipating. He pulled the fabric of my briefs tight, exposing my ass cheeks, then he gave each one a few good slaps."fuck." I blurted out, "that feels good."Then he peeled off my briefs and pulled me back onto the bed with him and spun me around so that my head was down near his waist. I knew what to do. I unfastened the belt of his robe and pulled it open. HIs cock was there for me in all its glory. He was neatly trimmed, with a little grey. His balls hung low and his cock, just semi erect, was already as long as mine. I took it in my hand and began to stoke it. Then I leaned in and began to lick him around his balls. He tasted musky and salty and I kept licking his balls and up along his shaft towards the head. He let out a soft moan and I could feel his hand stroking me too. Then I worked my way along his shaft with the flat of my tongue until I reached the tip, then I rose up and engulfed his cock head into my mouth.Now I started to go a bit crazy with the sexual heat and energy. I really began to give him head as his hands roamed around my cock and ass. I don't know how long I worked on him, but I began to feel his cock twitch a little and I tasted precum in my mouth. Then he pulled me up and put me on my back. Again, he was on top of me, kissing me, probing with his tongue. Both his hands were on my ass cheeks and I spread my legs high and wide. I felt his cock on mine and I lifted my legs hoping it would plunge into me. He pulled back and I could feel his hardness rubbing along my crack. I continued to grind. I could feel my own cock leaking precum down onto my belly. Sweat poured from our bodies."Fuck me." I pleaded. "put it in, come on, fuck me."He paused with the head of his cock pressing against my hole. "Have you ever been fucked?" he asked, very calmly and kindly.I shook my head no."It might hurt a little to start, but I can be gentle.""I nodded."He backed off and reached for a condom. I just lay there waiting, watching, precum still leaking from my cock and my ass aching to be filled.He deployed his condom. HIs cock was every bit 7", maybe longer, but very thin. He spread some lube on his cock.He climbed up to me and took me by the legs and began to turn me over."I think you will find it better, easier this way." He said.I didn't argue. Now I was on my belly propped on my elbows. He put a pillow under my hips and I spread my legs and waited.It seemed to take forever, and then he did something that almost made me cum.Instead of mounting me and driving his cock in, he attacked my ass with his mouth. I nearly flew off the bed and I did knock my head off a brass rung on the headboard. My body tensed. electric."Oh GOD!!" I shouted as his tongue lashed my asshole. "OH FUCk"What a feeling. My ass was on fire. My hole, my crack, ass cheeks, everything, and like unconsciously, I grabbed the bars on the bed and reverse arched my back to open my ass up to him. He assaulted me to the point where I was nearly cumming. Then it stopped. I was up on my knees panting hard and in a daze.I felt something, the lube I guess, and then he was up behind me again."Spread open," he said and I felt his hand pushing down on the small of my back. I reverse arched again and spread my legs a little wider. Then I felt him guide the head of his cock to my hole. I felt pressure building. Pressure ... Pressure... then his hands on my hips and pop! his head was in.It stung, no, it hurt and I tried to pull away but his strong grip held me. Then he slowly withdrew and the pressure subsided then bang!! he thrust back in hard. One, two, three each one deeper until he settled with his cock fully buried in me. He stopped.It was a shock. Gently, he stroked my hair. "Relax, relax" he said soothingly. "Just let yourself relax and open up."I was panting, tense. I began to calm a bit. I tried to relax my anus and to just let the tension ease away. As I did, the pressure subsided and the stinging sensation began to fade. I inched my ass forward withdrawing his shaft a bit, and then resettled pressing back until he was fully in again. I did this a few times and each time, I began to feel better. Then he began moving slowly and gently back and forth, a little in, a little out. It was not uncomfortable any more. Slowly, a little more each time, a little more out, then back in. He built up a steady pace. He adjusted his angle and I spread wider. Now his cock was riding in and out of me and it was starting to hit some sweet spot. it felt good. My cock was rock hard again and starting to precum again.He increased his pace. I urged him on."Faster, go faster. I heard myself saying. Sweat was pouring off me again. "Fuck me, Fuck me." I demanded. He was going fast now. He must have been sliding his full length in and out, his thighs slapping my ass cheeks faster faster, harder harder I implored him and then I could feel an orgasm building. HIs fucking was driving me to orgasm. I grabbed my cock and jerked wildly which just made my ass tighten "He grunted, OH FUCK. TIGHT, I'm coming!!" and he did just as my own orgasm hit. I collapsed forward with my cock spewing cum into his sheets as his cock filled my ass. A warm glow enveloped me.He lay on top of me. Both of us absolutely spent. It was the most intense orgasm I had ever had. I just lay there until his cock went soft. I think I napped a bit. I was done.
