Imagine someone being 58 and a virgin! It happens I guess, for whatever reason. In Danial’s case it was a combination of low self esteem and some childhood trauma I suspect. We didn’t get into it too deep. I’m just guessing.
I met him on altkink.com. It seemed a strange site for a guy who had never been with a woman. I guess he liked all the bondage stuff on there. it is a dark site. I suspected he had some pretty kinky fantasies being on there.
He was a really nice guy though. We exchanged numbers and talked late into the night a few times. Unlike most men he wasn’t really pushing for a meeting. He was shy and reserved and just kinda taking things slow. He wouldn’t admit it but I’m pretty sure I was the first woman he even talked to on the site or on the phone about sex.
He was a well to do bachelor but had never married obviously. Just worked and worked. He lived close to Toronto in a big house by himself. He’d actually first discovered me through my Blog and then followed the trail to my profile on the site and contacted me to see if I was really real, and the kind of woman I claimed to be.
We got to know each other like that for a couple weeks. Just talking on the phone, not only about sex, but his work, my work and other things we liked to do.
Finally it was time to meet. We met for dinner at a restaurant we both knew on a Friday night. He looked like his pictures and said I looked better than my pictures. I told him flattery would get him everywhere with me and we laughed.
He was a big man. 6’4, glasses, balding, big belly, but really soft spoken and nice. A total nerd, and he was for sure a virgin. He just had that vibe big time. he wasn’t your usual “gawk and grope” kind of guy.
I felt so tiny compared to him. He didn’t have any cock picks on his profile so I didn’t have any idea how big he was. I was pretty sure he’d be fucking me in the near future though.
We had a nice dinner and there was no real talk of sex. Just light flirting which he was terrible at. He did try though.
At the end of the evening we went out separate ways and he said he’d give me a call, which he did the next day. He said he really wanted to do this. He thought he’d worked up the courage. Would I come out that evening. “Sure” I said.
The dinner date we’d had really didn’t have any sexual tension on his side. Yeah I was excited but not as excited as I usually get, when my body goes into over drive. I hadn’t even worn anything sexy. Just a dress. It just felt like meeting a platonic friend.
Now things were different though. There was sexual tension in his voice and between us. I was horny all day. I did my gym routine, laundry, errands, and it was time to get ready. I had a nice long bubble bath that my nether regions and nipples, tingled throughout.
I had those butterflies in my tummy I so often get before one of these experiences.I picked out a tiny black dress, panties, and heels. No reason to wear a bra I figured, or much at all if it was all coming off right away, or so I hoped.
It was a 45 minute drive to his house. I’d naturally set things up with a friend telling them where I’d be for the evening just to be safe.
His place was big and beautiful. A very large treed in yard that hid a big beautiful house. He was successful at whatever he did. I had asked him why he’d never got an escort to help him over the hump but he just waved that suggestion away and said he could never do it with someone he had no connection with.
He was out on the step waiting for me as I pulled up the long drive and parked. I got out of the car carry my heels as I walked barefoot across the gravel driveway. That would have been fun walking on with heels.
He invited me in through the big doors and followed after me. He gave me a tour and , wow, what a place. I knew he was in the tech industry so he was doing pretty well for himself. Again I was reminded how tiny I was compared to him.
We ended up in the sitting room drinking whine eventually and chatting away like we’d know each other for years, not weeks. he was so smart and articulate, yet inhibited in some ways. We smoked a joint and loosened up a bit, well me, a lot. I came to the realization I was going to have to take the lead here. I’ve never had to take the lead.
At that moment he said “So how do we proceed here?”
I told him the bedroom would be a good place to start, and up the stairs we went. There was a cool breeze blowing in windows he had open. My nipples were erect and they hadn’t gone unnoticed by him I could see.
I was tipsy and incredibly stoned. I have zero inhibitions when I’m stoned like that. He seemed to have less as he just started getting undressed as he looked at me to do the same. Not much foreplay tonight I thought. But it’s not like he would know how to engage in that with zero experience I guess.
I dropped my tiny dress and stepped out of it with just heals and panties on. He said I was more beautiful than he’d imagined I could be. Out came the “Flattery will get you everywhere” with me comment ,and we laughed.
He was butt naked now and turned around to face me. OMFG, his dong and balls were fucking huge. His cock wan’t like 12 inches, maybe 8, but thick, curved, and hard and pointed at me.
“Ok”, I thought to myself in that split second. I’ve had big dicks before, but not as big around as a pop can. I was going to be getting stretched tonight for sure. The condoms I’d brought would fit, but snug. His cock looked like a dangerous mushroom with a thick shaft. His dick had a big head too. I’d never seen balls that big though.
I’m really not that big, I’m small and slight, but we’d be giving it a go. As long as he was gentle I’d be Ok I figured.
I told him all this. I’d have to be on top for sure. He was fine and seemed a lot less inhibited since we’d smoked that joint and then went on to tell me he’d never smoked a joint before or seen a live naked woman. Sure he jerked off to porn on the net, but that was it.
Anyway, to make a long story shorter, we ended up, him on his back on the big bed, me beside him with just my heels on….he insisted, he liked the heels…and me jerking him off. I had to sit up and use two hands and some lotion.
He lay there eyes closed and breathing heavy as I worked his big cock. He hadn’t even touched me yet but my body was on fire stroking for that reward his big balls had to give me. His big belly heaved up and down as he got closer.
Finally he grunted and gasped as he shot an enormous load for me. His big belly and my hands and wrists were covered in his cum. Eight big squirts, then several contractions as he shuddered, and he was done.
I was soaked down there. I was ready to climb on and go for a ride but we had to clean up first. We cleaned up and ended up back on the bed toking and drinking some more.
“I want to be inside you sooooo bad lonny!” he said.
I wanted him inside me too I told him. I got a condom out of my purse and slowly and carefully rolled it onto his big cock while he lay there watching me. I had some big ones. He stretched it but it was on and I was on next.
I was soaked. I climbed on and straddled him and told him to play with my nipples. I felt like I was in heaven as he gently pinched them while I got his cock head in position and started inserting it. Slowly the head went in as we both groaned. I sat down a little more and he went deeper as I shivered. It felt so good. More of him went in me as I leaned forward and then backed onto him.
I was stretched by him but not in a painful way. I gently rocked forwards and backwards and my body opened to him. I was afraid I was going to cum before I got all of him in me, or that he was going to cum to soon.
I had about 7 inches of him in me when it was enough. I began riding slowly as we both groaned and enjoyed each others bodies. It was heaven to have my tummy filled up like that but with no pain.
I rode slowly until we both came at the same time, me screaming and him grunting like an animal. He’d read enough of my Blog to know to give my nipples a hard twist when I came. I passed out and gushed all over him as I always do when a man gets it right.
I came to on top of him. Both of us were breathing heavy. He said it was the greatest experience of his life. I had no energy to respond. i just lay there catching my breath feeling his big dick slide out of me.
I rolled off and onto my back covered in sweat. We chatted for awhile and drank a little more. His inhibitions seemed to be gone now as he got more comfortable. So comfortable he asked if he could cum on my face and breasts.
I thought it was funny. Sure, why not. After resting a while, he got up the energy, straddled me, and jerked off on my face and breasts. I kept my eyes and mouth closed and let the warmth spread as he grunted and came for me yet again. It took awhile and he didn’t have as much left in him but he gave it up.
It was late now and we got cleaned up. I had a shower and left. I talked to him last night. I’ll be seeing him on the weekend 🙂
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