Begin With His End In Mind

It had been a long day at the conference and I was sharing a few drinks with a guy I had met there. It was after dinner and we hadn't eaten so the alcohol was taking effect as we were passing comment on the shapely arse of the bar maid.

Tony commented on how nice it would be to get her in the sack and then shocked me a little by saying "I bet she would take it up the arse." I laughed off the suggestion but he continued " Do you like doing it in the back door Gary." It may have been the drink that made me reply honestly "Well Tony, to be honest I have never had the pleasure."

Tony appeared surprised. "Are you saying you have never had anal sex with a woman?"

"Well….yes" I replied "I have often thought about it but the wife isn't interested. What is it like?" I enquired.

"So different from straight sex" said Tony " I don't know why more people don't do it."

"Well I assume it may hurt the woman" I said.

"Not if you do it right" he said "But then again I am just guessing" he smiled.

After a few more drinks, Tony, a 42 year old guy with a medium build, joked that we should share a cab and a girl.

I jumped at the idea and invited him back to my hotel room where we quickly rang a local escort agency. The receptionist asked us what we wanted and I said that we were after a skinny lady to share. The receptionist said she would see what she could find.

After a few more drinks and stories of past sexual encounters we were both fairly horny when there was a knock on the door. As I opened it I saw a young girl, not all that attractive, but a fairly good body and shapely arse. "Come in" I said.

After fixing Sue a drink Tony said "Gary here has never butt fucked anyone. Are you up for it?" Sue bluntly replied " I don't do that." "We will pay you extra, money is no option" I said.

Sue replied "For $1000 one of you can, but only one. OK?"

Tony and I agreed to pay half and then toss a coin. I didn't see the result which I think Tony may have rigged in my favour. "She'e all yours" he grinned.

Quickly I stripped off to my boxers as Sue undressed too. Laying on the bed next to her we embrassed as I pulled her closer. As Tony stood watching, my hands ran down her smooth, lean body until my fingertips touched the band of her knickers. The good thing about a hooker is you don't have to worry about foreplay. My index finger soon found her swollen clit and wet lips (she had come prepared). I slipped my finger into her and she parted her legs slightly. I almost jumped as I felt her hand rub my rapidly hardening cock and quickly she had pulled it out of my boxers and massaging it expertly. Realizing that she was trying to finish me by hand, I pulled away and asked her to kneel up onto all fours.

Tony had began to undress as I was now moving behind Sue, my 7 inch slender penis now as rigid as a rock. I felt butterflies in my stomach like I did before I lost my virginity; in a sense I was about to again. Sue had bought the KY gel which I now used to gently rub on along her crack, spending some time lubing up her tight sphincter.

As I knelt behind Sue as she pushed her skinny arse higher into the air. My cock was near bursting. I pushed the purple head of my circumsized prick between her arse cheeks. Sue pulled away slightly as the tip of my cock made contact with her sphincter. I placed my hands on her hips and pulled her back towards me. As my rod docked with her secret opening I was as hard as I have been for a long time. Slowly I applied pressure until her little bud opened to my touch and swallowed my head. I was actually inside a butt for the first time. I pushed in further, bit by bit, as Sue drew her knees up further under her stomach to push her arse higher into the air. I slid all the way in. I had my cock buried in an arse for the first time and I liked it. Sue began moaning and moving as I withdrew. Looking at the greasy shaft of my rod I was straining to maintain control as I plunged back into her, a little easier this time.

Tony crawled under the woman that we had bought and began licking her empty box, nibbling on her clit. This caused Sue to moan more and me to quicken my pace, pulling her onto my hot rod.

Then something happened which I wasn't expecting. I felt Tony's tongue licking my balls and sucking my balls. This was almost more than I could bare. Feeling the rising orgasm swelling in my loins I again slammed into the open anus offered to me. Losing some control, in a spasm on convulsions, my cock slipped out of the snug hole just as I blew my huge load. A stream of hot cum splashed onto Tony's chest and face. I shot 5 or 6 times and felt my knees go weak. I was embarrassed that I had cum on another man, yet strangely turned on by the sight of my white cum on a hairy chest.

I had fucked my first arse, came on a mature male who was to be my mentor , and I had loved every minute of it. What to do now? I looked to my mentor for instruction.

If you want to be Tony, email me at the address in my profile.