Fucked for the First Time at 50!

For many years I considered myself bisexual but I repressed my homosexual side, masturbating to fantasies of guys, but doing nothing about it, never having any real sexual contact with other guys. I thought I could be happy just fucking women, but as I got older I longed to explore the other side of my sexuality. Eventually, through the internet, I started meeting up with guys when I was out of town. For the next few years I had many hot anonymous sexual adventures with guys, but it never involved anal sex. I was ok with kissing, I loved making out, naked body contact, frottage and mutual masturbation. If I really trusted the guy then maybe I would suck his cock.

As I got older I got more and more into sex with men. One day, while away on a business trip, I met up with a gay airline pilot, "Jack". I was 50 years old by this time, Jack was in his late 30's. We met in my hotel room, and that first evening we kept to the rules I set beforehand. We kissed, we made out passionately, we got naked on the bed together, touching and caressing and licking and kissing each other all over. We rubbed our hard cocks together, I lay on top of him and we frotted together, humping against each other, our bodies sliding and rubbing together as we kissed. Finally we lay in each others arms and jerked each other off, stroking each others throbbing cock till we shot our cum all over each other.  Afterwards we showered together and cuddled naked on the bed.

This session was hot, but Jack wanted more. As we cuddled he kept admiring my ass, looking at it, stroking it, kissing it. I am a runner and very slim and I have a cute little bubble butt. He said he loved my little bottom, it really turned him on and he really wanted to make love to me, to fuck me. Finally I agreed to think about it, and we agreed to meet again the next morning, when we both had the whole day free.

I thought about his desire to dick me up the ass all night long. Should I try it? If I ever wanted to, now was the time. I really liked and trusted this guy, he was handsome and hot, with a nice but no-too-big dick, and I loved the way he got so turned on by the sight of my ass. Also, I knew he would be very gentle and would respect my limits. Did I really want to try having a penis in my bottom? Was I ready to let another man butt-fuck me? Could I be a "bottom" for a horny top guy? Early that morning I emailed him and told him to bring lots of lube and condoms, I was willing to let him try to fuck me!

I was both excited and VERY nervous when Jack arrived at my hotel room. He calmed me down right away, hugging and kissing me tenderly and telling me that we were going to take things VERY slowly, we had all day and all night to do this. We sat and kissed and he ran his fingers through my hair. Our tongues met in our hungry, hot mouths and our hands explored each other through our clothes. Soon we were ripping each others clothes off and heading for the big, king size bed. We lay there together naked, and he held me in his arms, kissing me and telling me how much I turned him on. I knew it, I could feel his rock-hard cock pressed against my thigh! We spent an hour just making out together, naked on the bed, fondling and caressing each other, lightly stroking each others cock, each of us moaning softly. He whispered in my ear that he longed to fuck me, to feel his cock inside my tight little asshole, that he wanted to make love to me, to enter me, to fill me up with his cock, to fuck me lovingly and gently.

Finally it was time to try it. Jack told me to kneel on the floor facing the side of the bed, then rest my arms on the edge of the bed and lean forward, lifting my ass a little. He took a big mirror off the wall in the bathroom and positioned it on the floor next to the bed so that I could see myself in it, and would be able to see him too. I would be able to watch him fuck me! Jack knelt behind me. He gently caressed my quivering bottom, bent over and kissed it all over, murmering words of appreciation for my "beautiful little ass". He caressed my ass crack, slipping his fingers between ass cheeks as he leant forward and kissed my neck and nibbled on my ear at the same time. Next he took a tube of lube and very gently started to rub the lubricant between my cheeks, deeper and deeper into my crack till he reached my little hole. “Just relax Alex" he whispered softly as he oh-so-gently massaged lubricant into my tight little virgin boy hole with his finger. He rubbed and rubbed and then he slipped one finger inside my asshole! It felt good, warm and pleasant. He finger fucked me for 10 minutes or so, gradually working up to 2 fingers penetrating my bottom, kissing me the whole time and telling me how much I turned him on.

After fingering my ass for a while, he took his hard cock in his hand and lay the shaft on my butt crack. He pushed a little and his boner slipped between the lubed up cheeks of my bottom. His dick was vertical in my butt crack, the head of his dick pointing up at my bare back. He leant against me and frotted his cock against my bottom, wrapping his arms around me and playing with my erect penis as he humped against me. It felt good to feel his big cock sliding up and down in my crack, and it looked hot in the mirror!

Next he pulled back and took his dick in one hand. He undid the condom wrapper and slipped the condom over his cock, then squeezed lube from the tube all over it. I watched in the mirror nervously.  This time he pointed the head of his cock right at the center of my butt. Slowly he moved forward, pushing the head of his knob between my ass cheeks, pushing it further into my ass crack till he reached my asshole. He stopped there, and just lightly rubbed his dick head against the entrance to my little hole. He rubbed and rubbed, massaging my tight little hole with the tip of his big penis. He whispered to me to relax again, and kissed me. "Are you ready Alex?" he asked. I mumbled "yes Jack, but I don't know if I can take it, I.."

 “Shhhhhh" he replied, kissing my neck again. Gently he pushed forward with his hips.  We rocked together like that for some time, with him holding me and gently pushing with his hips, his dick pushing at my back door, a little harder each time. I thought I would not be able to do this, but he was patient. He pushed a little harder as I got used to the feeling, then a little harder, then harder, harder, harder....suddenly my asshole opened up and the end of his cock penetrated right into me! I cried out and bucked as a wave of pain hit me, "Oww fuckk owwww!"

Jack immediately withdrew from my ass and turned me around, a look of great concern on his face.  "Did that really hurt bad?" he asked. I thought about it. "Well it hurt like hell when your cock actually slipped into me, but then a few seconds later I think it was OK."

"Man your ass is so tight, I don't want to hurt you," he replied. "Jack, it's OK, let's try again, I want to try again, but don't pull out right away even if I cry out again!"

Jack was so worried about me that his dick had gone completely soft. I pulled the condom off his limp penis and we climbed back onto the bed together. "Lets take a short break before we try again" he suggested. I agreed, then suddenly realized that I was hungry, It was lunchtime and I had not eaten anything yet that day. "You want something to eat?" I asked Let's order room service and eat in bed!"  And so we ordered sandwiches and drinks. When they were delivered I just wrapped a towel loosely around my naked body as I went to answer the door. Jack discreetly slipped into the bathroom.  The handsome young bellboy who delivered our sandwiches was clearly flustered. The "Do not disturb" sign on the door, the rumpled bed, sandwiches for 2, my nakedness beneath the towel in the middle of the day, the condom wrapper and tube of lubricant on the nightstand...it was obviousthat two people were having sex here. Of course he might have assumed there was a woman in the bathroom, except for the trail of men's clothes leading to the bed, two pairs of mens shoes, two pairs of briefs in the middle of the floor.... He actually blushed as he took in the scene, but I made him walk right I and put the tray on the bed side table!

Afterwards we cuddled together and laughed about it as we fed each other our lunch.

We started again. Kissing, making out, stroking each other. He moved me back to the floor, back to my position in front of the mirror. This time I knew what to expect. He fingered my asshole and I loved it. He rubbed his cock in my crack and I wiggled my hips, wriggling my bum against his cock. Then I opened up another condom. "I'm ready" I said "put this on". In the mirror I watched him slip the condom over his fully erect penis, then rub lube all over it. He took his penis in one hand and guided it into my butt crack, right up against my little hole. Then he gently started pushing again.

It was no easier the second time. It took a long time, pushing, pushing, his penis probing and prodding in my bottom, pushing a little harder, harder, harder...suddenly it happened again! "Oh fuckkk oooww fuck, ohh oww..don't pull out!" I cried in one stream of expletives and cries of pain and the instructions for him to stay inside me!Jack kept perfectly still, the head of his dick buried in my ass.  After a couple of minutes the pain subsided, and I just had this warm, full feeling. "OK Jack, push it in further, but slowly!" I said. Jack very slowly pushed forward, easing the shaft of his hard penis deeper and deeper into my bottom. It felt good! A bit uncomfortable, but good and exciting and not painful now! Slowly he pushed his dick all the way up my butt, till every inch was inside me, right up to the base. I felt his pubic hairs against my ass cheeks.

Jack paused again, and let me get used to the feeling of his manhood penetrating deep inside me. I felt filled up by him, possessed by him, taken by him, I was his and I had him deep within me. Jack put his hands on my hips. Very slowly he started to move, withdrawing his cock an inch or so, then sliding it back in.  He was fucking me I was getting fucked up the ass by a handsome young pilot and I was loving it! I watched in the mirror as he pulled out a little further, part of his hard, slippery, glistening cock shaft visible between our bodies for a moment, sprouting from his dense mat of pubic hair and disappearing into my ass., He pushed back in, ohhhhhhhhh now it felt soooo good! He increased the length of his strokes till he was pulling almost all the way out of me, just his mushroom head still inside me, then he would pause, then slowly slide his hard shaft all the way into me, balls deep. He whispered "Oh Alex, your ass feels sooo good, I love the feel of my cock in your ass, I love fucking you!" I replied "ohhhhhhh Jack, fuck me, fuck my ass with your big cock Jack, oohhhh I love the feel of your cock deep inside my bottom”

Very gradually Jack picked up the pace, thrusting his hips a little harder, thrusting in and out of me a little faster, then faster again. Soon I was completely relaxed and he was fucking me good, his cock sliding in and out of my ass, in and out, in and out, faster, harder. I watched in the mirror as his hips rocked and bucked and he pounded my butt, fucking me even harder, ramming his cock deep in my ass.  "Oh fuckkk yess Jack, fuck me, fuck me hard!" I yelled now, really getting into it. Jack was moaning loudly, and breathing very hard "Ohh fuckkk Alex your tight little ass feels sooo good, oooh oooohhh, oh fuck I love fucking you!" I reached between my thighs and stroked my own cock a little as he fucked me, masturbating myself as I was getting a fucking. I noticed a pool of my pre-cum on the rug underneath me.

Suddenly Jack slowed down, then stopped. "Alex I don't want to cum yet, let's make it last" he gasped, panting for breath. And I agreed, we had all day and all night! Jack carefully pulled his cock out of my ass, then pulled off the condom. My ass felt a bit sore, but basically OK. Both of us were hot and sweaty, so we decided to take an erotic shower together. We climbed under the warm water together and let it run all over us, then we soaped each other up all over, caressing and fondling each other with the suds. Afterwards we dried each other off, then we cuddled together on the bed for a while, and discussed what we had just done together. Soon we were both ready to do it again!

This time he led me over to the sofa. He sat me on the sofa and knelt in front of me, facing me. He lifted up my legs and put them on his shoulders, and I lay back, my ass rotating into view for him.  Gently he lubed his fingers and finger fucked me again, then he slid on another condom. I thought it would be easier this time, but it was not, but we tried again and he pushed and pushed and "OH FUCKK" he was in me again!

We fucked like bunnies on the sofa and he leant forward and kissed me as he dicked me. I was his!  He was deep inside me and staring into my eyes. He moved faster, faster, he pumped and pumped and pumped. We were both moaning loudly again. When he was almost at climax he pulled right out of my ass and ripped off the condom, let out a strangled cry and shot a huge load of cum all over me!

Afterwards we went back over to the bed. He held me in his arms and stroked my cock while whispering in my ear what a great fuck I was, how much he loved having his cock up my ass, how much he loved to fuck me. It did not take long for me to finally reach my own huge orgasm. I shot a fountain of cum high in the air, and it splashed down all over both of us. Wow!  That had been an incredible experience.

Afterwards my asshole was a little sore for a few days, but it soon felt fine. I often masturbate while thinking about that cock in my ass.......