Date: Tue, 6 Apr 2010 01:06:28 -0700 (PDT) From: Chuck Hughes Subject: Learning to please - part 5 This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further. As we stood, Howard tied his bathrobe about himself and took my elbow, maneuvering me over to the couch. Without the slip on I felt the cool air along the opening to my crotch and backside. Howard deftly slipped a hand down between my cheeks and gave me a firm squeeze as he motioned me toward the couch. He asked if I wanted something to drink & I said yes to some more juice. As I sat there, I wiggled from left to right and flexed my ass to see if my hole still felt slick. It seemed to have tightened up and I figured that I needed to re-lube it. Howard came back with my drink and we sat for a while and talked about the wild sex we had just enjoyed. "So by the way," he ventured "I noticed that you haven't cum yet - did you want to go masturbate before we move on to more exciting things?" I immediately noticed two things. First - he distinctly wasn't offering to participate - If I did it, it would be by myself. Second, although I was extremely turned on and flushed with desire throughout the day, my cock was never at raging hard-on level. It fluctuated between slightly thickened to shrivelled and shrunken. I told him "Well, no, not really...I mean I'm really enjoying myself, but I just don't think I need to do that..." "Hey, it's cool baby..." he grinned, rubbing my neck. "But if you don't mind..." I continued, "I would like, um, a little privacy beforehand to, um you know, clean up and get myself ready..." "Oh, sure - of course...after you finish your drink, why don't you head back to your room? You'll find some lube in the nightstand you can use...I'll come back and join you in a few minutes." There it was: I was minutes away from getting a cock in my ass. I gulped my drink and tried to remain calm, smiling a little. He leaned over, gave me a kiss and told me "Better hurry up or I may bend you over and take you right here...". I stood and slowly walked down the hall, wobbling on my heels. Inside the room I found the lube - a new box - opened it and set it on the nightstand. I kicked off my keels, pulled off the panties and walked into the bathroom with the banana, a new condom and the lube I had brought with me. Not wasting any time I squatted and pushed 3 lubed fingers into my hole and started prepping my bottom. A minute later, I had the condom on the banana and it was deep inside of me. Comfortable with that amount of preparation, I wiped my bottom clean, applied extra lube to my ass lips and washed my hands. Seeing myself in the mirror, I realized that I needed to redo my lipstick - and then I gave myself a few more spritzes of the cologne. I went back to the bedroom, slipped on my panties and folded back the comforter and top sheet on the bed. As a last minute thought, I ran to the bathroom and came back with a clean bath towel which I laid in the center of the bed. A small hand towel I placed on one of the pillows...just in case. I got onto the bed and kneeled facing the open door, and sat back - waiting. I realized that I was glad to be out the heels as my feet were sore and I rubbed them briefly. My heart was racing fast as I sat there, but then it doubled in speed as I heard Howard moving down the hall. He stood in the doorway and looked me over. "I hope you're ready for this...'cause I need to feel my cock deep in your pussy baby" he said quietly. "Yes, I think I'm ready...I'm ready for you baby" I said. He slipped off his robe and let it drop to the floor. He reached down and took hold of his thick shaft and gave it a menacing shake "You're about to find out why women love to be pounded by a big cock - you sure you want this?" "Yes" I said, holding out a hand "Come on, don't make me beg for it" I gushed. He laughed and walked to the edge of the bed, taking my hand and pulling me up to him, giving me a kiss as he squeezed me tightly. As I kneeled at the edge of the bed hugging him, his strong body squeezed against me and I felt so small. We slipped into deep hot tongue kisses and his his hands held me tightly. His belly was pressed against me and I felt his thickening cock coming to life and bouncing against me. One hand held the back of my neck as our tongues played. His other hand found the opening in the body stocking at the small of my back and slowly eased down, under my pantie, taking my ass in his hand. His middle finger naturally slipped between my cheeks and landed right at my rosebud. I felt his grip grow tighter as his other fingers started to force themselves between my cheeks. His finger was gently probing and immediately pushing into me. Somehow, reflexively I squeeze shut and pulled back, every so slightly. His reaction was immediate - his strong arms crushed me back against him as his finger pushed deeper. He pulled his face back and looked down at me, grinning. As his finger entered the slightest bit I gasped, being up on my knees like this was an usual position and it all felt much tighter than I thought a finger would. My heart was pounding because he had such control over me, actual physical control - I knew I couldn't resist. And, I knew I didn't want to resist - I wanted this to happen. He laughed lightly, smiling, seeming to enjoy my awkwardness. He looked into my eyes and assured me "Just relax baby, it's gonna be fine - I've done this before, the first time is always a little weird, but you'll get used to it. You know you want to feel cock in you and this is the way it happens - just relax and give into me," he said. I pressed my face against his neck, wanting to surrender but also wanting to hide my face which was flushed with embarrassment. He was right, I wanted to feel cock in me, I was there specifically to get fucked and I wanted him to do it to me. "Shhhh, that's a girl, just relax" he soothed as his finger backed away from my hole. "Spread your legs a little, that's it, now lean back a bit" he said as he loosened his grip on my torso, allowing me arch my back, pushing my butt out slightly. His finger was quickly pressing against me as he whispered into my ear "Just push out a little with your pussy". The puckering of my hole made his entry easy and his finger slipped right in to full depth as held held me, rocking his hand slightly. He started moving it in and out and I felt myself relaxing and moving with the motion. He moved his face to look down at me, grinning once again. "There, that wasn't soo bad, was it?". I blushed back and smiled as he kissed me. His finger was now actively rolling, stretching me open. "Here, let's take these off" he said tugging at my panties. I sat to the side and he helped slip the panties off my legs and dropped them on the floor. "Stay right here" he said, as I reclined across the end of the bed. He left me and walked around to the side of the bed, wiping his hand off on the hand towel I had placed there. He picked up the lube and squeezed a good amount into his hand. As he walked back I took a moment to glance down and was relieved to see that my small cock was soft and just a slight bulge hidden in the material of my fishnet bodystocking. Self consciously I closed my knees to hide this. "Let's make sure you're good and ready, ok?" He asked. I nodded yes up to him as he positioned me across the end of the bed, on my knees. He gently pushed my head down, leaving my ass high in the air. "That's a girl...open for me" he said as he moved my legs to spread me open. His one dry hand was rubbing my ass cheek very gently as his other hand came up and started playing with the rim of my hole. He bent down and nibbled at my ear as this was going on. "You smell so good baby, that perfume you chose is really nice, thank you for looking so good for me" he whispered into my ear. His dry hand traced a trail down my back and landed on my hip as his he moved his face down to my behind. I knew he was intently watching my 'pussy' respond to his ticking and probing and it caused a tingly feeling in my stomach. I felt his lips make a slow, wet kiss on one butt cheek and then the other. I felt his grip on my hip tighten as he abruptly started to work two fingers into my bottom. I felt myself wiggle and squirm a little - wanting to slow the pace of things - but his grip tightened on my body and he continued with his entry. "Shhh, don't fight it" he whispered "You know this hot ass needs to be fucked, so let me get you ready". I tried to relax and just let it happen and he quickly was working two and three of his thick fingers into me. I was starting to enjoy the feeling, the motion, when he stopped and switched to having both hands kneed my cheeks, with his thumbs opening me further. He stopped and my bottom felt empty and I wanted more. I rocked back and pushed my 'pussy' hole out and let out a soft whimper, hoping that he'd know I wanted him to continue. He stroked the small of my back but his voice was deep, almost menacing when he said "Yeah, I know what you need, you need to get pounded like a whore, don't you baby?". He came around and rolled me over so I could look up at him. His cock was at full erection and he had a gleam of lust in his eyes which was a little frightening. I lifted myself up to lean on one elbow as I gently cupped his nuts in my small hand. Hoping to lighten the mood I said with a soft, demure voice "You know I want to please you Howard, I came here to learn, and, and I know you need to shoot your load, and, and...come on honey, don't make me beg for it". He grinned down at me as he picked up the hand towel and started to wipe his hands with it. He threw the towel over me onto the bed and took hold of his cock. He gripped it tightly as precum rose from the slit. With one finger he wiped a smear of the precum and lifted it to my face. "Lick it" he demanded. Obediently I opened my mouth, stuck out my tongue and reflexively close my eyes, taking his finger into my mouth, sucking. I opened my eyes as he groaned with anticipation, withdrew his finger and cupped my face. "You're so hot baby...why don't you get up in the middle of the bed and make room for me to join you?" I eagerly scooted up onto the bed and fluffed together some pillows to lay down on. I laid down on my back, keeping my knees together but bent and feet spread apart, like I had seen women do in Penthouse magazine. He smiled and picked up the lube again, squeezing a large amount into his palm and applied it to his cock. He wiped his hand off and threw the towel up to the pillow by my head. I watched him nervously as he climbed onto the bed at the foot and approached me on his knees, with his erect cock straining straight out. I took a moment to enjoy the sight of his massive hairy body, his wide belly, and his huge thick cock. I was trembling and panting in anticipation of being under the man, feeling him enter me and taking his seed - pleasing him - giving him relief. "Oh baby, you look so good to me, I need you soo bad" I heard myself whisper. As he approached I opened my knees, spread my legs and shifted my weight down to slightly lift my feet off the bed, allowing him an opening to embrace me. He stopped before me and ran his hands down my smooth legs to the ankles, lightly tickling my feet (I giggled) and back up my legs, to my inner thighs, across my stomach and up to my chest where he massaged my breasts through the fishnet material. I closed my eyes and enjoyed his touching. His thumb and forefingers expertly plucked at my nipples and sent shivers through my body. As he played with me I felt him inching his body closer and soon my feet were resting on his thighs. He stopped playing and let his hands trail away. As I opened my eyes he was hovering right over me with a needy, lustful look. I glanced down and saw his thick cock and was terrified - shocked that somehow it seems much larger than any banana or cucumber I had used. I reached up and placed my hands on his chest, slowly moving them around to gently stroke his biceps, hoping to impart a last reminder to be gentle with me. His hands came down to cup my ass. "You need to roll over, doggie style" he grunted. I was a little confused, clouded and he smirked "You're not read to be fucked like a woman yet...I don't want you pushing me off, now get that hot ass up here bitch so I can make you mine". "Yes honey, ok..." I started to say but he was already using his hands to flip me over. I collapsed in front of him and he roughly laughed and patted my behind teasing "Get up there bitch, you know you want it". "That's a girl, show me you want to please your man" he continued as I crawled into position in front of him on my hands and knees. I was humiliated and horny and my head was spinning. He had one hand on the small of my back, pushing me down into a squat. the other hand was under my bottom, a finger probing my rosebud. "Squeeze it baby, work that pussy" he said as I tried to comply by flexing my bottom, pushing out and spreading myself open for him. He moved his body in closer and in between my legs - his thighs were pressed up against the backs of mine. He now had both hands on my hips, holding my firmly. I felt his cockhead pressing against my bottom and I tried to shift left and right to provide a little wiggle room for it. Howard held me firmly and slowly but steadily pushed forward a bit, then eased back. At one point the head started to move in, but there was pain and I started to pull away, lifting a hand up in a gesture asking for him to stop. He stopped, but held me firm, slightly impaled on his cock. "Baby, there's no time outs in this game" he laughed meanly at me. "I need to sink this cock into you, and you know that you need it in you. Look at you" he continued "makeup, women's clothes, high heel shoes...shit, you need this as much as I do so don't make me force you" he said with a slight thrust of his hips that made me wince. "Come on now, the first time is always tough on the girl...but I need this...you owe me baby. I think I've been very good to you, you can't hold out on me 'cause I got a big dick. Let me love you baby" he said bouncing slightly against me. He was right of course. I did want it and somehow I did owe him, or I wanted to think that I owed this to him. I had fantasized about taking cock - big cock - his big cock - into my bottom. I had come this far... "If you want to leave, I'll call you a cab and you can go back to college dressed like a girl if you want..." he chided "or you can help us both feel good and get what we need". I looked back and my long legs and thought how beautiful they looked in the bodysuit and how horny he must be. At this point his hands were playing with my nipples and I was feeling very sexy. I withered under his gentle touch, I neede a man to make love to me. "Now, how about you drop you hand like a good woman and let me take care of this...trust me baby, you're gonna like it...". "You're right baby, I'm sorry I just...you know...it is a little painful..." "How about I get some more lube, ok?" he asked. I dropped my hand and nodded yes, I was too embarrassed to look at him. He got up and came back from the bathroom with a thick layer of lube on his cock. He climbed on the bed and got in position behind me. As he wiggled in he lifted my body up so I was kneeling, leaning back against him. He produced a small bottle which he said was a popper for me to inhale. I had no experience with anything like that he simply held a hand on my should and told me it would be alright, it helps women comfortable with large cocks. He told me it would be ok and to trust him...he didn't want to hurt me and wanted this to be good for both of us. As a gently reminder he started working the head of his cock back under my bottom. Feeling a little desperate I consented and he instructed me to let out all my air and take a deep breath through one nostril while I held the other closed. He held the bottle to my nose as I breathed it in I and he gently held me and whispered to me "Yeah, that's it, more more more, good girl...breathe out...ok one more time, more more yeah baby that's good." The drug flooded my mind and I was instantly very drowsy, dopey but also very awake. His hands rubbed up and down on me as I leaned back against him. I was dizzy and felt him nibbling my ear and kissing me. It was delightful, electric. He was pushing up with his cock, trying to have me sit on it. I knew this position must be uncomfortable for a man of his size so I leaned forward again, on my hands and knees exposing my ass to him. He was on top of me immediately, one hand on a hip, the other on my shoulder. Through the fog of the drug I felt the pressure and some muted discomfort as he tried to force his cock into me. He said "You're ass is so hot you must be burning to feel my cock in you". "Yes" I moaned out loud, he was so right, I needed that cock in me, I was burning and needed to be filled. I leaned forward and grabbed a pillow to hug, dropping my body down. This allowed my spinning head to rest, kept my ass up high for him. In my heart I knew this was the right way to let him have me. "Goood, baby...that's the way you need it right?" he laughed "Ummm yes baby" "Are you sure you're enjoying this, do you really want to get fucked, because I can stop it if you want" he laughed as he bucked his hips, poking his cockhead into my hole but not yet fully penetrating. "Please baby, don't laugh at me, you know I need you in me" I moaned. He stopped laughing and shifted his position a little, using both hands to plant me firmly in place. He started to push in earnest and was grunting with exertion. I felt a 'pop' as his cockhead penetrated my bottom. He froze and then I gasped as he continued to push in. He withdrew and started again and kept at it getting a little further with each thrust. Once again I was aware of some pain and discomfort, but it was not terrible and I really felt great. He stopped and I looked back over my shoulder. had I been a few years wiser I would have known not to say what I said - "Are you done honey?" He laughed, a big laugh that had his belly shaking as he lightly slapped my ass "No, I am far from done with your sexy ass. We need to change positions now so I can sink my cock all the way, now that we have you loosened up". He pulled out and let me sit up for a moment. I was pleased to notice that there wasn't any blood or obvious filth from my bottom on his cock or on the bed. As he lubed his cock I held my hand out for him to squeeze a little into mine, so he wouldn't have to touch my hole. This also gave me a chance to feel what was going on down there. I was happy to find out that that everything felt moist and a little puffy. Howard noticed what I was doing and came over and said gently "Hey, is everything alright?" placing a hand on my shoulder. "Yes, I'm fine...thanks..." "Because I don't want to hurt you" he said sounding genuinely concerned. I smiled, "No - everything is great, this is good" Howard tickled my ear "Because you really are beautiful and I am so glad you came over today" He started to stroke one of my breasts as he offered me the bottle again. "Take a little more" he smiled "Because you're going to be taking a lot more of this" he said tauntingly as he shook his cock. I took two more deep breaths of the vapor as Howard encouraged me. Howard piled a few pillows up in the middle of the bed for me. "Same as before" he ordered but this way there's no weight on your knees". My head was spinning again so I was glad to lay down and let Howard position me the way he wanted. This time he climbed on top of me and I felt his whole body weight pin me in place. At his instruction I reached my hands back and pulled my butt cheeks apart to help him guide his cock in. With a little shifting around in a moment his head was pressing at my ring and had popped in. He stopped and whispered in my ear to ask if I was ok? "Yes baby this is what I came here for - be my man" Without a moments hesitation he gripped my body and started to press slowly, firmly, continuously into me. I felt my body quiver and I held his hands against me, willing him to take me. The drug fogged my brain but I felt the burning sensation as his cock pressed deeply into me. He came to a rest and a was surprised to hear my voice whimpering in what could have been pain or ecstasy. He stroked my neck "That's it baby, that's my full length". He withdrew with a long slow motion, and repeated his entry. He started rocking back and forth, letting his hands come down to grip my ankles as he picked up the tempo and started thrusting away. As the pounding knocked the air out of my lungs I gasped "take me, take me" as I felt beautiful sensations wash through my body. Howard continued his thrusting with amazing strength and motion. His hot sweaty body pressed against me and he wheezed as he kissed my neck. After a few long minutes, Howard stopped and flipped me off the pile of pillows and onto my back with a twist of my ankles. Pausing as he knelt before me, he let go of my ankles. Without a word I spread my legs for him and leaned back, lifting my feet, knowing what he needed. Howard caught his breath as he scooted in closer, he huge cock glistening, veiny and red. "Hold the headboard and don't run away, I'm not finished with you yet" he commanded. Not comprehending what he meant I reached back and placed my hands on the padded headboard as he mounted me and started thrusting again. As he worked his massive hips against me he held me down by my arms, kissing me, taking delight in my enjoying the ride. His face changed and became serious. His pumping changed and he started going for longer deeper thrusts that just folded my body in half under his weight. He grinned wickedly down at me and said "Now it's time for you to earn those high heel shoes baby" He was grunting and wheezing and thrusting wildly and I knew he was cumming. Cumming in me. He came to a stop, breathing heavily, smiling down at me. I was also out of breath - his thrusting had once again knocked the wind out of me. "Thank you...thank you Howard" I gasped. It was uncomfortable for me with all of his weight on top of me and my legs flailing out to the sides of him - pinned. He got up and slowly withdrew his cock from me, rolled me onto my side, laid behind me, and slid his cock back into me, holding my back against his chest. It was very relaxing as we laid there and caught our breath. Offhandedly I was amazed at how easily he had re-entered me just now. Howard's cock was still thick and full inside me as we rested. End Part 5