The Meeting

Author’s Note: This is a true story, but I’ve not used names to protect ourselves. Please send reviews! If you'd like to post this elsewhere, obtain permission from me first. I'll probably say yes.

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We emailed and talked on the phone many times before meeting. It was decided that we would meet at an upscale hotel in a city halfway between our houses. We’re both single, you a 35-year-old doctor and me a 25-year-old student.

You gave me explicit instructions on how I was to groom and what to wear. I followed them to the letter. I had black thigh highs, a thong, and sexy lace bra on, with an outfit over them. My skirt was so short that if I sat down or bent over, the tops of my stockings showed. I shaved myself everywhere, leaving no hair on my legs, armpits, or crotch.

You arrived first and checked into the hotel, calling me and letting me know what room to come to. I arrived less than 5 minutes later. I was nervous when I knocked on the door, but was put at ease by you. There was something about you that made me trust you immediately.

We kissed passionately for several minutes. You put your hand on my ass, feeling for my thong, making sure I followed your instructions. You squeezed it, feeling my cheek. I excused myself to the bathroom, freshened up and returned to the bedroom. You had undressed down to your boxer-briefs.

You ordered me to get on the bed, and I did so. I slipped off my shoes and faced you, waiting for directions. You took out a bandana and put it over my eyes. I could not see anything. You told me to lie on my stomach, and I knew what was coming. In our emails, I told you I was an anal virgin and wanted to experiment with it. I knew you were going to give it to me.

You ran your fingers up and down my slit, causing me to moan. I felt something cold hit my back end, and realized it was lube. I heard a vibrator start and felt you put it into my pussy. You were getting right down to business. The lube was rubbed into me very well, with you occasionally putting one finger into my anus. I thought this would hurt a lot, but it didn’t. I really liked it and moaned more.

Once I was really wet, you put two fingers in me. This caused a little pain, but I still thought it was great. I felt you get off the bed. Then I heard what sounded like a rubber band, but realized you were putting a condom on. I heard you squeeze the lube bottle again, and knew you were going to do it. I wouldn’t be an anal virgin for long.

I felt you move back into place behind me. Your cock rubbed back and forth over by anal region, settling against my anus and placing gentle pressure. At first it did not seem like it would ever fit, but as you kept pressing, I relaxed myself and felt your dick move slowly into me.

The much clichéd “pop” of the sphincter muscle did not happen, one moment you were pushing against me, the next you were inside of me. You leaned down on my back more, to give yourself a better angle, and kept moving farther inside me. This was all a little uncomfortable, but bearable.

You moved slowly back and forth. The vibrator made me feel so good, but after a couple of minutes it fell out of my pussy. I moaned very loudly and constantly. Then you started talking dirty to me, and I loved it.

“Tell me you like this.” You demanded.

“I love this.” I replied in a small voice.

“Louder.” You commanded.

“I LOVE THIS!” I almost screamed. You started moving faster at this. I was starting to hurt at this point, but decided to keep it to myself. I thought the pain would end eventually. I moaned more, this time from the pain, not pleasure.

“You want this cock in your ass, don’t you?” You asked.

“Oh yeah, I want it.” I answered. My moaning was getting louder and louder as you moved slightly faster and faster. I couldn’t take it anymore, so I told you it hurt too much. You stopped moving and said, “Okay, we’ll go real slow.”

You did move slower, but the burning feeling I was having just kept stinging. I wasn’t enjoying it at all, so I asked you to please stop. You pulled out slowly. I could feel my anus still open from your invasion. I still could not see anything, as the blindfold stayed on through all of this. You told me to roll over onto my back, so I did. I felt you move up closer to my face, and I knew what was coming next. Your cock hit my chin and cheeks as I tried to get it into my mouth.

I had very little experience with blowjobs, but I sucked it as best I could. You moved your hips back and forth, fucking my mouth gently. You knew from my emails that I wanted to learn how to deep throat, so you tried my limits by pushing yourself farther and farther into my mouth. I tried to relax as much as I could and take you as far as I could. My gag reflex is really strong though.

I gagged, my eyes watered and my nose started running. I got more spit in my mouth and kept sucking and licking as best I could. You pulled out of my mouth, I felt you move away, then lie back down on the bed.

You took the blindfold off and I saw your erect cock for the first time. I was amazed that it got into my anus at all, as it was really thick. I looked up at your face and smiled, knowing I had pleased you a little and accomplished something I really wanted to do. You smiled back and said, “Suck it.”

I lowered my mouth down to it and took the head into my mouth. I took as much as I could into my mouth, but started gagging more easily. You stopped me and gave me a quick lesson. You showed me where the most sensitive spot on your cock is. It was about an inch square area below the head. When I touched it with my finger, it made your cock jump a little. I loved having that power over you.

You told me to massage that area with my tongue as applied suction with my mouth. I did this for a long time, over and over again. You moaned frequently and told me when it felt really good. My jaw didn’t ache like the other blowjobs I had given. I was really impressing myself with my sexual prowess.

Apparently the only part I wasn’t doing up to your standards was the “hand” part of the job. You pushed my hand away and down to your balls, so I could caress them. Your hand replaced mine on your cock. I kept my mouth as far down as I could, but your hand stopped me to some extent. You were pumping your hand up and down very hard and fast. I knew you were close to cumming.

A couple of minutes later you said, “Here it comes.” I’ve never had a man cum in my mouth, and really want to experience it, but I chickened out at the last minute. I pulled my mouth off, and you came onto your stomach. It was a great turn-on to see your orgasm.

This was the end of our sexual escapades that night, but I hope there are more to come. I would love to have you as a “fuck buddy.” For the next hour we lay on the bed and talked. You got up, I got straightened up as I hadn’t taken my clothes off, we kissed good-bye, and you went to take a shower. Until next time…