0 comments/ 73561 views/ 3 favorites Begin With His End In Mind By: gedda98 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. Begin With His End In Mind Ch. 2 Here is the second Chapter many of you have asked for: Having just experienced my first butt fuck with the hooker, I liked it and wanted more. I couldn't help wondering what it must have feel like to have a long cock up your arse. Tony had already turned of the light and climbed into his bed as I just stood next to mine in my boxers. "Are you alright Gar?" he asked. "Umm...yeah" I replied. Then I did the most astonishing thing. As if by remote control, I walked over to Tony's bed, pulled back the doona and cotton sheet and laid down next to him. For a man I barely new and never having experimented with a guy before, this was not normal behaviour. "Lonely?" Tony quipped. I just looked at him, noticing his smiling eyes. "Have you ever made love to a guy before?" I spluttered out. "Well... I have played around before" he replied. With that I felt his hand brush against my thigh. I rolled over to face him. Looking at each other we new, without saying a word, where this was headed. "Teach me" I whispered as my face pulled closer to his. Briefly we kissed as I felt his hot wet tongue slide into my mouth. Tony's hands began to run over my back and torso. My hands caressed his hairy chest and I jumped a little when his strong hand slid under the elastic of the satin boxers I was wearing. I laid back and enjoyed the touch of his fingers searching through my blond pubic hair. I was surprised to see how quickly I had grown hard, a hardness I hadn't had for a long time. Dragging his knuckles over my now throbbing shaft, Tony slowly dropped his head, licking down my chest, over my abdomen, until his face was just above my boxers. Suddenly his fingers wrapped around my long slender shaft and he had me in his right hand while his left hand pulled my boxers down, unveiling my still damp light brown pubic hair and my cock wrapped in his large hand. Inches away from my swollen knob, Tony's mouth prepared to taste me. I had never had a blow job from a guy so I was looking forward to the new experience. His lips gently brushed the head as his eyes looked up at mine. Slowly he opened his mouth and covered the top of my dick with his wet lips, as his fist began to slowly pump my shaft. I arched my back and groaned. Tony took the full length of my hardness into his hungry mouth. Being a male meant he knew what felt good and this was one of the best blowjobs I had ever had. Wanting to explore more I whispered " Swing your body around and let me taste you." Tony quickly complied and as I rolled on top of him with my cock still being sucked, his Y Fronts were now within reach so I could return the favour. Gently I pulled the cotton material over his obvious erection and out sprang his rock hard rod, framed by dark pubic hair. I was about to taste my first man. Copying his technique I bean to slowly pump his rod with my fist as I lowered my head over his pelvis. Slowly my wet mouth opened as Tony pushed up his hips. The head of his cock was surprisingly hot as it brushed against my lips. I quickly dropped my head and took his whole length inside my mouth and throat. I ran my tongue along his shaft and softly around the tip of his meat. It must have been OK because Tony was moving in time and let out a satisfied groan. We were having a 69er on those clean cool white cotton sheets. Minutes passed as we slurped and sucked each other. Almost involuntarily I relaxed my body and spread my arse cheeks over his face so that my tight virgin sphincter was looking Tony in the eye. Electricity shot through me when Tony unexpectantly traced his middle finger along my crack until he reached my tightness. I braced myself as he inserted the long finger into my arse. All this while we still were blowing one another. As I had climaxed earlier with the hooker, my staying power was good. Tony however had not cum yet tonight and I could sense from his groans and movement that it wouldn't be too much longer until he did. This left me with a dilemma : I so wanted to taste his hot salty cum and lick him clean, however I also needed to feel him shoot his load deep inside my virgin arse. What was I to do? Well mentor tell me. If you have a suggestion or wish to play Tony's role, email me. Begin With His End In Mind Ch. 3 The question was to answer itself. As I felt my shaft being swallowed by Tony, I shivered as he placed his large hands on my arse cheeks and spread them further. Again I felt a surge as his tongue left my rod, slid along my balls and up along my crack. The tip of his tongue pushed against my virgin hole as I pushed down onto Tony's face. As I felt him enter my anus with his sharp tongue my balls contracted a little. Even though I had cum not long ago, this was rapidly building another one. The only thing I could do in this 69 position was to suck Tony's rigid penis, pumping him with my fist. And then the answer came – well Tony did anyway. Unexpectedly I felt him arch his back and mutter " I cumming" – which was a little too late as by now I was tasting my first ever serve of cum. The hot spurts first hit my tonsils as I had swallowed him just as the first spurt erupted forth. Tony had seen and experienced a lot of action that night so he had built up quite a load. The second spurt covered my tongue as Tony moaned uncontrollably. The third spurt hit my lips and my chin as he withdrew from my mouth. The taste was sensational. I had occasionally tasted my own cum from the lips of my wife or girlfriends but never before had I drank straight from the source. Tony's cum was salty and thick and I kept my mouth shut enjoying the feeling of his cum in my mouth before I swallowed as much as I could. Some had leaked out and my face had a shiny glisten on it. I licked his shaft for what seemed like minutes. He had lost his stroke on my dick as he had collapsed into exhausted pleasure. I climbed off him and he crawled along my body softly kissing my skin until again we were face to face. Tony laid next to me and we kissed. I felt his tongue licking mine, tasting his own cum. After some time he drifted off to sleep as we laid in the spoon position. I couldn't sleep as my head was spinning with the intoxicating smell of man sex and I was still hard having recovered from my earlier time with the hooker. However as I lay there I new what I wanted next required Tony to be given some recovery time. After some hours, he stirred and began to caress my body again, kissing my nipples until they were erect. Moving down my body his kissed my stomach however I was surprised when he skipped over my stiffening rod and began to lick my balls. Mmmmm I thought. Then, as if reading my mind, his tongue continued down and I was compliant as he parted my legs. This allowed him greater access to my arse and in particular, my tight, virgin bud. Again electricity shot through me as I felt his wet tongue flick against my anal opening. I lifted my left leg, spreading myself open to this lover I barely knew. Tony appeared to enjoy the experience too as he began licking my opening with some vigor. "Are you alright Gar?" he asked. I could barely respond. Then I was again pleasantly surprised by his next move. Slowly his tongue left my bud and he replaced it with his finger. My back arched as his middle finger pushed into me. I could feel the knuckle pushing into my puckered sphincter. The tip of his finger caressing the inner walls of my arse. Tony moved up my torso and again we kissed. This time it was me that tasted myself on my partner's tongue. With my legged still raised up, Tony's hand could still reach my arse and his finger was working its magic. "Well Gar" he whispered in my ear "what do you want now?" It was a tease. He knew what I wanted – what I needed. It is important to state here that to allow another person to enter you is an incredibly intimate gesture and I can empathize with how a girl would feel immediately prior to losing her virginity or having sex. The fact that right then I wanted my arse to be filled with a rock hard cock that would shoot a full load of hot cum deep inside me was pure passion. "Tony, I want you to fuck my cherry arse. I want you to cum deep inside me. I want to return the favour to you. Deal?". Tony knew when a deal was too good to refuse and I could see his cock grow another inch. "How do we do this Tony?" I questioned. "Get on your hands and knees and I will ride you like a dog." He laughed. I rolled over and tucked my knees under my damp stomach. The palms of my hands lay flat on the crisp white cotton sheets. I lowered my head and raised my virgin arse. Tony knelt behind me and I could see he was rock hard again. I felt rather nervous, rather exposed, rather inexperienced and I loved every sense of it. My mind shot back to the hooker I had earlier had in the same position. Now I would know what she felt. I jumped a little as Tony placed his right hand on my raised bun. "Don't worry, I will be gentle" he mocked me. Tony leant over me so I could feel his breath in my ear. Then I felt the tip of his cock brush against my crack. Involuntarily I pulled away. "Relax" he said. "Tony I want you to fuck my hole now" I replied. And he did. I felt the head of his cock push between my cheeks and nestle at my virgin opening. The tongue bath he had given me earlier had provided some lubricant and he applied a little pressure. I pushed myself back on him. I needed a dick in me so bad. Finally the head of his shaft split my anal lips and pushed into me. Inch by inch I accepted Tony's rigidness into my arse. When I felt the length of him inside me and his pubic hair tickling my arse cheeks, I pushed back further onto him. I wanted more. It hurt initially, but the pleasure and the thought of having a cock up me countered any discomfort. When Tony slowly withdrew for the first time, Ifelt empty and quickly pushed back onto him. As the sweat from our skin covered his rod, Tony pushed into me a little faster. "Fuck me" I groaned. Tony again quickened the pace and I could feel his balls slapping against mine. My cock was as hard as it had ever been and just swaying in the wind. Tony put his hands on my hips and rode me hard. I pushing back on his thrusts and he was grounding out, only to then withdraw the whole length until I felt only the tip against my now gapping hole. Slam in again. By Tony's reactions I could tell he would soon cum. But this was my first (maybe last) arse fuck and I wanted it to last. "Lie down" I told Tony. He had some trouble stopping pounding my tight arse, but I pulled away and rolled him onto his back. He soon realized what I had in mind. I wanted to go on top. Grabbing his shaft I knelt over him and lowered myself over his erection. Spreading my legs wide I sat on his cock. He slipped into me as we looked into each others eyes. I now controlled the pace. Lifting up I pulled his cock out of me and then slowly sat on it again until he was deep inside me. I massaged his chest. I thought of fisting my own cock and spraying my cum over his chest, but decided not to as I wanted to fuck him as well. Up and down. "I cant last much longer" Tony grunted through clenched teeth. I wanted to feel him blow deep inside me so again I climbed off him and resumed the Doggy position again, this time raising one leg to allow greater access. Tony climbed behind me again and pushed his tortured shaft up my compliant anus. "Give it to me" I teased. After one or two violent thrusts Tony was about to fulfill both my dream and me. The heat of his cum surprised me. As he thrusted into me he exploded deep inside me, and I could feel the heat of his cum in my bowels. Tony shot spurt after spurt deep inside me and I drew him in further. After his convulsions had ended, we just stayed in the same position for minutes, needed of us could talk. I had been fucked for the first time and loved it. When he finally pulled out of my quivering hole, I felt his cum trickle out of my ravaged hole and down my thigh. Tony collapsed on the bed. "Well, your turn now" I asked. "What should we do now? Any ideas?" Email with further ideas.