Warning.! Adult Material - Adult Themes - Adult Content - Warning.! This material is copyrighted. Oscar Hargraves 2011. This is a work of Fantasy and Fiction. It is NOT a true story and is not based on any known facts. Any resemblance between names, places and characters in this story to anyplace or anyone, living or deceased is purely coincidental. The author does NOT support or condone the behaviors portrayed here. This work is copyrighted and you do NOT have permission to copy, post or use this for any reason except your own personal reading pleasure. Copyright Oscar Hargraves, 2011. By continuing to read beyond this point you are guaranteeing: 1.) You understand the above statement and agree to the limitations below. 2.) You are NOT an agent of the government, 3.) You are not affiliated in any way with any law enforcement agency, 4.) You are not breaking any laws in your area by reading this material. The Incident with Pollyanna - MW oral anal reluc Let's call her Pollyanna. That's not her real name of course, but sometimes I like to look back and remember her that way. A woman of intelligence and power, Polly commands the respect of her community. She is a dynamo of activity and organization on any given day. She's also a manager, writer, organizer, supervisor, teacher and leader. Unlike some of the Subs I've read about, Pollyanna is bright, articulate and intelligent. I finally got to meet Pollyanna eight months ago when I was on a trip back East. Now let me make something perfectly clear here. Polly was not a fashion model or a beauty queen. She wasn't the `knock `em dead' raving beauty that so many of the writers today claim to have met. Instead she was what I term a `real' woman. Yes, she carried a few extra pounds, (don't we all?), but what Polly did have was the best attitude and the most beautiful smile that I have ever come across. She could look into your eyes and it felt like she was looking right into your soul. When she saw someone she liked her face would light up, and, it seemed, so would the room around her. The world was a better place when Pollyanna smiled, at least as far as I could tell. We had met online and chatted with one another many times. I had always sensed that there was something special in this lady and I wanted to know more about her but her career and her personal life was far divergent from mine so I never felt we would meet. Then two years ago I retired from the airline I was flying for and took a job as a corporate pilot flying a twin engine Beechcraft KingAir and hauling executives all over the country. One day after I'd been there about 14 months, I was assigned to fly the CEO and his party to a large city near the eastern seaboard. As I was flight planning for the trip I realized that this would put me less than 100 miles from the lady I chatted with so many times on the computer. I quickly logged on and sent Pollyanna a note saying I MIGHT be in the area and was she free to have dinner with me IF I could make it? The flight was uneventful (the very best kind!) and we landed ahead of schedule. The boss said he would be there at least three days and maybe four. Since this was early Friday evening, I was told to be back at the airport and ready to pick them up the next Tuesday morning by 9 AM. I quickly called back to our corporate offices and told the scheduler the situation. He said that it was cheaper for the company to have me stay there rather than fly all the way back and then return next Monday or Tuesday. I, in turn, suggested that I could fly up to a field where an old friend of mine from the military lived about 65 miles away and park the plane there at no charge. Since this would also save the company some money, both in aircraft parking and hotel bills, he was quick to agree. I called my friend and got permission to land and park in his hangar. He also volunteered his extra car for me to use if I wanted to do any sightseeing. This I quickly accepted but failed to mention the only sight I wanted to see was less than an hour away from his home and airport. When I called Pollyanna after I landed she was excited and pleased to hear from me. She assured me that she definitely was free for dinner and was starved so would I please hurry. She said she had to grab a shower and she'd be ready when I arrived. My trip was short and quick and in no time I was standing at her door. She answered my knock and for the very first time I actually laid eyes on this wonderful lady. The key word here is `eyes'. The first thing you notice about her is the sparkle in her beautiful eyes as they dance merrily. Then the large winter coat that was wrapped around her full figure. I will admit though that my eyes did stray and come to rest on her marvelous cleavage and those warm soft mounds of flesh that were partially visible inside the overcoat. As my eyes returned to hers I saw her blush and knew that she had seen my stare. She invited me in and informed me that she was running a little late. She had just gotten out of the shower when I knocked and had thrown on the coat to come to the door. She still had to dry her hair and get her make-up on. As I followed her thru her house and to the door of the bathroom, I quietly slipped the present I had brought her onto her kitchen countertop. I knew of her love for crème liquors and had stopped to pick one up as a special gift. I was pleasantly surprised when she entered the bathroom and removed the coat without closing the door. Her smile was a little nervous at doing this so soon as if she was afraid it would give me the wrong impression, but her eyes watched me and spoke of trust and love as only a true Submissive's can. I won't bore you with the details of dinner. Suffice it to say that we talked about everything. By the time the meal was done and the wine was flowing, we were discussing more personal things. As I drove back to Pollyanna's house I noticed her looking at me in a way that I hoped meant a great weekend was forthcoming! We walked up onto the old porch and I stopped to give her one more chance to bid me goodnight and send me on my way. Instead she unlocked the door and we entered her home without another word. As she closed and locked the door behind us my heart skipped a beat and I walked back over to face her. I stared into those eyes and slowly leaned down to kiss her warm passionate lips. My kiss was returned with interest and I soon had one hand sliding down the outside of the back of her blouse to the small of her back. As I kissed her lips my fingers played a symphony on her spine and danced along her back. Her arms both went around my neck and her kiss became an invitation. I slowly pulled away long enough to look her in the eyes and ask, "Are you sure this is what you want?" Her answer was to lean into my chest and kiss me again. At this point I knew that this was going to be a dream come true. I kissed this lovely woman back with a passion and that passion was fanning the fire that was quickly building in my loins. My hands found the strap of her bra through the fabric of her blouse and began working the clasps. As my fingers deftly unhooked the bra I felt her melt into my arms even more. This woman knew what she wanted and I knew that I was about to experience something wonderful and very special. With a shy smile Polly pulled away slightly and lifted her blouse over her head. Next the bra slipped from her shoulders freeing those wonderful large breasts with their firm nipples. The shy smile continued as she took my hand and led me off to her bedroom. There she quickly removed her skirt and stood before me with only her panties on to hide her womanhood. I knew from our conversations, both online and on the phone, that she was timid about her body. She felt she wasn't pretty enough, that she was too fat and that no man would want her. Boy I have to tell you; all I could think about was how lucky I was and how much I wanted to show her she was wrong. As I stepped in to kiss her again I felt her hands start to reach between us and unhook my belt. Soon she had my zipper down and a soft warm hand was sliding carefully into my pants. My excitement was obvious to say the least. That hand found my shaft and long soft fingers wrapped themselves around the length of it. As my pants slipped to the floor I released her and unbuttoned my shirt, which I let fall to the floor. My hands were now able to explore her beautiful body. The soft mounds of her breasts felt absolutely wonderful as my fingers ran over them and squeezed their warm flesh. A soft sigh escaped her lips as I pinched and twisted her dark brown nipples and helped them grow even larger. Polly's eyes were closed now and she was standing perfectly still as my hands continued to abuse that soft flesh. Without waiting I leaned down and took one nipple in my mouth while I rolled the other one back and forth in my fingertips. I could feel her heartbeat increase and knew that she was liking this attention. With my left hand on her right nipple and my mouth on the left one, I let my right hand trail down her tummy and across the front of her panties. The heat there was exciting but I knew there was more. My hand moved gently around the back and again starting dancing along her spine. Not hard now but softly and gently accentuating the sensations I was inflicting on her breasts. The hand would travel around her back, down her spine and around to the front again. On one of those trips the fingers encountered a very wet area in the front of the panties. Without stopping my gentle assault on her breasts, I carefully slipped one side and then the other of her silk panties down until they slid below her knees. Then I pushed them to the floor as I carefully backed her up to the foot of her own bed and turned her around. Pollyanna was and is a true Sub. Without releasing my hard cock she slowly lowered herself to a kneeling position in front of me. Her back was straight and her head slightly lowered as she stared at the hard piece of man-meat in her right hand. I noticed her tongue slip out and wet her lips as I took a half step forward. Her mouth opened and quickly engulfed the head of my throbbing member. Pollyanna was an experienced cock sucker who loved her work. Her warm soft lips closed over my manhood and began to move up and down the shaft while her tongue moved about underneath and explored all along the bottom of my shaft. Polly never looked up. With here eyes closed, she now had both hands on me. One hand was holding my balls gently as her wonderful mouth worked on my hardness. She used the other hand to reach around my waist and push or pull my back so that my hips were moving forward and back in time with her head as it bobbed up and down. In no time at all I could feel the heat rising in my loins and I was fighting to maintain my control so I didn't blow too soon in her marvelous mouth. Polly sensed my attempt at control and redoubled her efforts. She was determined to have my seed. On one trip down my shaft I felt the head of my cock slip past the entrance to her throat. The next pass was the same but the third time down, Pollyanna had her nose in my pubic hair. As if it was completely natural and easy, Pollyanna was deep throating me. Her warm lips would slip all the way down my shaft and grip my erection as her head raised back up again. A half a second later she was sliding back down with my hard meat going all the way into her throat. Then her lips would close and she'd repeat the process. I was in heaven. Just when I thought it didn't get any better, she pushed my hardness all the way into her throat and held it there. Then her soft tongue slipped out and she started caressing my balls with her tongue while my cock was planted deep in her throat! That was it. I couldn't stand any more. The heat that had been simmering and rising in my body turned into a volcano. My hot molten lava streamed up the tube racing from my balls up the shaft and leaping out into her mouth and throat. She sensed the flow as it started and bobbed her head up and down to help it while never letting my throbbing cock slip from her throat. I felt like I had exploded inside. I shot one hot load of man-juice deep into her pulsing throat followed quickly by two more. As my third load slid down her throat, Pollyanna pulled back and tightened her lips around my shaft. I knew she had to breathe and forced myself not to grab her beautiful hair and drive myself back down her throat to that place of awesome warmth and sensation. After grabbing a few breaths through her nose and without having her lips ever leave my cock, she was again in motion. This time her mouth was slowly sliding up and down as she licked and cleaned every inch of my slowly dwindling hardness. When her lips finally left my cock and it fell free in the warm air, I felt like I was now within this wonderful lady's spell. I had Pollyanna stand and kissed her firmly to show her how much I had loved what she had done. Then I used my hands to guide her body around until she found the bed behind her and melted down onto it. She slid up a short distance but was stopped by my hands on her knees. Her eyes fluttered open questioningly but closed as she saw my smile. Now it was my turn. My hands slid along the outside of her thighs to her knees and then to the inside of her calves as I lowered myself down and kneeled at the foot of the bed.. My fingers were again at work moving, caressing and playing along her skin. To this I added the soft touch of my breath as I gently leaned forward and inhaled the aroma of this woman. My warm breathing left a trail along her thigh and up to her nether regions where is moved the few tiny hairs above her neatly trimmed pussy lips. I sensed her breathing intensify as my lips found her thigh and my tongue started tracing a path along the inside of her leg. Back and forth, up and down first on one leg and then the other I was carefully worked to build her excitement. Her rapid heartbeat and motions told me that I was indeed getting to her as the tip of my tongue found the top of her love nest and flicked gently at the small hard nubbin that was protruding there. As my hands separated those wonderful thighs, my tongue probed deeper into the heaven that awaited there. Gentle flicks and sharp jabs, followed by swirling motions and long hard deep probing with my tongue soon had her wreathing on the bed. My thumb and forefinger held her open while my experienced tongue stretched and reached for, but not quite to, he `G' spot. The combination was enough to send her over the top twice in rapid succession. Before Polly could recover from her second massive orgasm I climbed on the bed and drove myself fully into her hot wet cum-box. She grunted as I drove myself home and then wrapped her arms around me. The velvet glove that is her pussy wrapped itself around my hard cock and immediately started squeezing it in a rhythmic manner as her after shocks coursed through her body. Again I looked into those glorious eyes and saw so many things there. Love, trust and longing were there, as well as her submission and desire. As I kissed her passionately I began to thrust in and out of this woman whom I had waited so long to meet, I knew I was going to have trouble controlling myself and my orgasm. Already I felt the need building and the desire to shoot a huge load of hot man-juice deep into her waiting loins. I was determined not to do this until I was sure she was cumming again too so I worked slowly, concentrating on moving side-to-side and up and down as well as in and out. I lifted one hand off the bed and started to squeeze one of her lovely tits while I suckled hard on the other one. The moans that were escaping her mouth told me that I was on the right track and soon I felt her hips join with my mine in that age-old rhythm that has driven men wild since the dawn of time. Now her feet were back on the bed and she was using them to raise her hips and meet each of my thrusts with a counter-thrust. Her tight pussy would open to allow me access and then squeeze shut as I tried to withdraw. The result was a milking motion on my hard cock that had me ready to cum in a very short time. As Polly's head rolled back on the pillow and her breath got shorter I knew she would soon be on her way to that place that only a woman can go. I carefully continued to work on her soft lovely breasts, first sucking one nipple and then the other while I drove myself in and out of her hot womanhood. It soon became clear that her orgasm was rapidly coming. With a renewed vigor I started to drive myself even harder and faster into her tight cunt. I raised myself up on both arms to allow her to breathe and to get better leverage as I drove my hard cock into her with wild abandon. Faster. Harder. By now the bed was rocking back and forth and bouncing the headboard off the wall with an awful thunking sound. That sound only partially covered the noise of my hips as they slapped into hers and I drove my hardness deep into her body. Just when I knew I couldn't hold out a second more, I felt Pollyanna start to shake and shudder. Her pussy gripped my raging cock like a soft vice and her eyes rolled back into her head as she shot up the ladder of her climax and burst through into Nirvana. As she was reaching her peak I felt the heat of my desire begin its trip from deep in my loins. It came racing up through my throbbing cock and shot out in huge spurts coating the inside of her womb with hot sticky man-cum. I held my cock there, deep in her body and enjoyed the sensations of filling her with my love-seed. As we both came sliding back down into reality I felt that warmth and glow that only comes with total satisfaction. Day two: Saturday Pollyanna woke to a pleasant surprise. I had made us both a breakfast of crisp bacon, eggs over easy, toast, juice and, of course, lots of coffee and had it ready when she woke up. Since we had never made it to our dinner date last night and had barely had to energy to shower before collapsing in bed, we were both famished by now and ate hungrily. After breakfast we dressed and went out for a ride so she could show me around the town. I have to admit that I don't remember much of what she showed me. I was too busy just staring at her and reminiscing about last night. When we stopped for a late lunch at a small restaurant where everyone knew her, she introduced me as a `friend who had stopped for a visit' and everyone seemed very pleasant. By 3 PM we were both tired and headed back to her house. We decided to watch some TV but there was nothing on we wanted to see. Soon we were snuggled up on her bed and she was dosing off to sleep. Polly came awake about 7 PM with a start. At first she couldn't figure out why she wasn't able to see anything. Then she tried to wipe her eyes and found that her hands wouldn't move! She quickly realized that her wrists and ankles were securely tied to the corners of her bed frame and she was lying flat on her back, blindfolded and helpless in the middle of her own bed. I watched her lick her lips and try to decide whether to scream, call out for help or wait to see what would happen. The latter seemed to win out as she visibly calmed herself and waited to see what would happen next. Like I've mentioned, Polly is an intelligent woman with smarts and savvy. We had talked online several times about some of the BDSM things that we liked and wanted to try. In `real life' she is always in control and smart enough to be both a great leader and a friend to her employees, but she had said that she liked being a bedroom Sub/slave. Now I wanted to see if she would be willing to take that further and try something new. I watched the emotions flick across her face as she assessed her situation. There was no panic, no screams and no crying. She quickly assumed a `wait-and-see' attitude. With a slight smile I watched this from the comfort of my chair. I was slowly spinning the handle of the small feathered toy I had in my hand. Careful not to make a sound, I watched and let Pollyanna stew for some time. She didn't know if I was in the room, in the house or completely gone and I think this was what started getting to her. When I had determined her stress level had risen enough, I very quietly got up and approached the bed. With just the very tip of the feather in my hand I started tracing lines along her body. Soft, slow gentle motions produced a feeling similar to a large housefly walking on the skin. This I moved about never working in the same place for long and being sure that she could not predict where it would come next. After about 10 minutes of this I very quietly picked up my whip that I had waiting on the bedside table. Now understand that my whip is not for pain, at least this one isn't. This is a leather whip which is made of soft red suede and has about 20 laces. These laces now replaced the feather tracing lines around on Polly's lovely soft skin. As they moved across her breasts I noted the hardening of her large areolas and the way her nipples seemed to jump out with excitement. Her face and neck were now included as my attention moved about her helpless form. As the tips of the whip slid slowly across the lips of her labia I noted that her excitement was already evident from the moisture there. Now I replaced the whip with my fingertips. Slightly more pressure but only just enough to touch the skin and heighten sensations. Fingers traced paths around her nose and eyes, down her smooth throat and across her lovely breasts. Now they worked their way down along her belly and towards her nether-region. Never moving fast but not quite stopping either. The inside of her thighs received special attention as I moved in closer and enjoyed the pleasure/pain that I saw on her face. Gently I leaned in and flicked my tongue across her hard nipples. This got an immediate reaction as a long gasp escaped her lips. Using the very tip of my tongue I traced a line down her tummy and around the outside edges of her labia. Careful not to touch the pussy itself my tongue continued down along her left thigh and then back up. This was followed by an identical treatment of her right thigh. By now Polly was wreathing and begging. Her skin was on fire and her nerves were at the edge. Desire was evident in her every move as I worked my magic on her poor body. She was begging for me to fuck her, begging for me to put my fingers or my cock into her, begging for release. On the next pass my tongue moved across her hot pussy and flicked the hard exposed nub of her clitoris that protruded there. Polly jumped and wreathed some more. When I did this again I lingered a few moments and flicked her clit back and forth with my tongue. Then, without warning, I stiffened my tongue and drove it deep into her hot wet box. In seconds poor Pollyanna was out of control. Her senses that had been on fire before were now running on overload. Her body bounced and seethed as my tongue worked inside her and she would have been begging still but she couldn't catch her breath enough to speak. In only moments her orgasm was upon her. I reached up and softly pinched her nipples as the flood of emotion and sensations washed over her and she reeled off in ecstasy leaving a shaking then limp body behind on the bed in front of me. I was carefully lapping up every delicious drop of the wonderful nectar that had been streaming out of her beautiful cunt. Slowly, softly I continued to do this until every drop was gone and she was completely clean. As her after shocks subsided I watched as this beautiful woman returned from her first climax of the day and gasped for breath. Giving her only a few minutes to recover, I started playing with the engorged lips of her pussy again. My fingers worked across the top and then one at a time started to spread her open and enter her hot wet box. With two fingers inside her I reached up and quickly slapped her on the tummy. The shock of this caused her to flinch and buck which drove both fingers into her as far as possible. These I now bent upward and folded in such a way as to find her `G' spot. Now I flexed both fingers back and forth; sometimes together and sometimes separately. The result was an immediate reaction. Polly's poor pussy started to lubricate even more with her hot juices and her body was again wreathing about in the restraints. Now my fingers were going in and out as well as moving around inside. Her body, which had never fully recovered from the last orgasm, was now well on it's way to another. I knew this was going to be a big one. Polly was taking a long time this time to build up this time. I was pretty sure that she was on her way to a massive climax that would completely take over and use all of her energy. I continued my assault on her tight little cunt with one hand while the other found her nipples again. This time I crawled up on the bed alongside her bound body and started to kiss her panting lips while I regaled her tight box with my fingers. As I leaned down and sucked one of her hard nipples into my mouth rolling it around with my tongue and chewing ever so softly on the areola under it, I gently and carefully slipped my smallest finger under her box and began poking gently into Polly's tight back door. We had talked before about the one time when a Dom had tried anal sex with her. He had pushed her over and jammed his meat into her virgin asshole with no lube and no preparation whatsoever, expecting that as a Sub she would simply take this treatment and do what he wanted. She had told me how much that had hurt and how she had cried for hours after that terrible assault. She had also thrown him out and never seen him again. I was determined to show her that it didn't have to be that way and she could enjoy being used there too. At first she tensed up just a little but then the other sensations that were flooding her senses took control and she relaxed allowing my finger to slip all the way into her ass. During this time I had not let up my attentions on her tight pussy. My fingers bent and curled as they drove in and out of her. As I felt her orgasm growing and building to its peak inside of her, I opened my mouth and gave her my first order. "Cum!" I told her. "Cum now and cum hard!" That was all it took. This was the final straw. The dam burst and Pollyanna started gushing out her reply. I believe she would have been screaming but her breath was ragged and short. Her hips bucked against the invading fingers within her hot wet cunt and sensation overwhelmed her body. Polly was shaking and bucking as her climax peaked out and she slipped over into a state of mental and emotional bliss. She had entered that Nirvana that only a woman can find when she is totally and completely satiated and satisfied in every way. Day Three: Sunday I was awakened Sunday morning around 9 AM by the smell of hot coffee and fresh biscuits. I could here Polly singing to herself in the kitchen as she shuffled about making our breakfast. It struck me as funny when I realized she was singing `Devil Woman', one of my all-time favorite Marty Robbins songs. I stayed on the bed listening quietly for several minutes thinking about this woman and the way she made me feel. My little friend was awake too, with my thoughts affecting him, so I slipped out of the bed and headed for the shower. After her huge climax the night before Polly had simply collapsed and fell into a deep sleep. I had covered her up as I snuggled up to her back. When I finally fell asleep we were cuddled up like two spoons with my arm over her and my hand holding her breast. I noted the damp towel in the bathroom as I turned on the shower and slipped into the stall. Obviously Polly had gotten up earlier than I thought. My shower didn't take long. I lathered up and washed my hair; then I rinsed off quickly and stepped out onto her shower mat. Just as I did, I heard the door open and Pollyanna was standing there with a fresh hot cup of coffee for me. I smiled and dropped my towel as I reached for the cup and her eyebrows went up in mock surprise. Well what did she expect? She's was standing there with a thin, almost sheer nightgown on with her gorgeous tits sticking straight out at me. One look and my little friend was raising his head for a look too! Polly smiled seductively and said that breakfast was ready. Then she turned and walked out letting me glimpse the nicest little wiggle of her cute ass just before the door slid closed. That glimpse and her smile started more ideas spinning around in my mind. In no time at all I was dry and heading for the kitchen, coffee cup in hand. When I arrived I found that my place was set and a breakfast with those wonderful biscuits was already on my plate. Needless to say, I dug in with enthusiasm. We ate and talked and laughed. I loved the twinkle in her eyes when she looked at me and the way her hair shadowed her face just enough to make her look beautiful. Gawd, I was thinking; I'm really beginning to fall for this lady. Everything she did was a turn-on to me. After breakfast Polly started to wash dishes while I worked on my third cup of coffee. She was about halfway done when she suddenly turned around as if she had made up her mind about something and sat back down across from me. She sat there and looked into my eyes for several seconds before saying anything. I sensed that this was one of those times when silence, at least on my part, was golden so I said nothing and stared back into her face. Finally she broke the stare and looked down at her hands in her lap. "I don't exactly know how to say this," she stammered. I sat there and said nothing, waiting for her to get up the nerve to continue. It seemed like an eternity passed but I'm sure it was only a minute or two. Then Polly looked up again, looked deep into my eyes and said, "I want you to fuck me in my ass." Now it was my turn to not know what to say. Lust was already running through my thoughts as I remembered that cute ass wiggling in front of me this morning. Yeah I know some guys would say it was too big, but I didn't think so. In fact I thought it was gorgeous! Then the other memories came flooding in like a torrent of flood waters rushing in to ruin everything. Polly and I had been writing and talking for several months. She had told me about the one and only time that she had had anal sex. It seems this creep that called himself a Dom had been having sex with Polly for awhile. One day, without warning and without preparation he had simply bent her over and rammed his hard cock up her virgin ass. When she had screamed and begged him to stop, he had only laughed and continued to use her. By the time he was done and pulled out poor Polly was in severe pain and crying. Luckily she is a smart woman and saw the writing on the wall. She never allowed that fool to get near her again and made sure to pass the word out on that website that he was no Dom. She had told me that she would never let that happen again and would never do anal sex; at least not for a very long time! So you can imagine my surprise and shock when she said this to me. Polly was still staring into my eyes waiting for some sign from me. As my head reeled and my thoughts gathered back into my skull, I realized just how scared she looked right now. Without a word I pushed back my chair, got up and walked around the table to where she was sitting. I looked down into her beautiful brown eyes that were so full of emotions right now as her mind raced with the reality of what she had just offered to do. I put out my hand and waited as she took it and stood up. I pulled her close to me and held her wonderful body as she shook ever so slightly for several minutes. Then she seemed to relax as if she had made the decision to go through with this no matter what. She was definitely one of the bravest women I had ever met. A thousand thoughts all try to crowd into my head at once. Polly knew how much I liked anal sex. We had discussed this many times online and even once or twice on the phone as we talked late into the night about how she should do this, but what now? I knew about her bad experience and I knew she was hoping (praying? depending on? afraid of?) it happening again. I thought quickly about my overnight bag. Yes there were several condoms in there and I was pretty sure I still had a tube of anal cream that desensitizes the skin. That would be okay if she had some good lube to go with it. The problem was getting her to relax enough to even try this, because I was sure she was scared and nervous. If she didn't relax then we would have a repeat of her past experience with Dom X and I most definitely did NOT want that. All of this and more flashed through my mind as I looked into Polly's eyes. Now I saw the trust there. The fear was there too and no small amount of trepidation, but I knew she really wanted to try this. I wasn't sure if she was doing this for her own reasons or if she felt like she owed me something for the past 36 hours and wanted to pay a debt. I only knew that this would be a one-time, chance-in-a-lifetime shot at something that I had wanted since I stepped through her front door. I led Polly back to her bedroom where I started kissing her again. She was returning the heat of my kiss two-fold and soon my little friend was rising up to see what was going on. I guess he knew he would be needed and wanted to get ready. My hands slid down Polly's back and across her round ass. Then they traveled back up her sides with one stopping at the small of her back to massage the tight muscles there. The other one continued up and the fingers slid through her hair pulling her head even closer to mine as she opened her mouth and our tongues danced divinely together. Now my mouth was working its way down along her neck and then to those two wonderful boobs that I loved so much. Polly raised her arms and let her lacy nightgown slip to the floor. The her hands were behind my head pulling me closer to her breast as I suckled and licked on one then the other with abandon. My hands were still roaming all over her body, sometimes gently and sometimes firmly, working to heighten her sensations. Pollyanna released her kiss and slid slowly down my body kissing my chest and stomach as she went. When she arrived on her knees, her soft fingers wrapped around my manhood and started to caress it. She opened her mouth and, using the very tip of her tongue, began to tease the head of my cock with tiny flicking motions. Then her eyes looked up into mine and she slowly and carefully swallowed my entire length down her throat. She closed her eyes and began sliding up and down my shaft using her talented tongue to lick and move about the underside of my cock while she moved her head up and down the shaft. In a very short time she had me fighting for control so I wouldn't download a huge cum-shot into her hungry mouth. At this point, with some regret, I reached down and gently removed my throbbing member from her mouth. I helped her stand up and then laid her down on her back across her own bed in such a way that I could return the favor. I started out by licking and nibbling my way down her body paying extra special attention to those two wonderful tits that I had grown to love. I worked my way down her legs and finally across her hot pussy lips that were already dripping with desire. My tongue slid between her labia and traced circles around the inside before finding the growing bud of her clit. I slid that hard nubbin into my mouth and sucked it gently while my tongue continued to dance about inside of her. I was thoroughly enjoying the reactions I was receiving as Polly arched her back and tried to force even more of her hot dripping pussy into my mouth. By this time I knew Polly was really turned on so I carefully slid one hand around and began using my finger in her pussy. When that finger was wet and slippery I would take it down to the brown puckered hole just below and run the finger around and around there. Then back up for some more lube and repeat the process. The first time I did this I felt Polly tense up as my finger worked around her anus, but she soon relaxed and continued to enjoy the treatment my tongue was giving her hard clit and wet pussy. On one trip my finger slipped inside that backdoor and started to work around inside. Gently.... Very gently I moved about, stretching her ever so slightly and getting her to relax and enjoy the feelings. By the3 time Pollyanna had gotten over the initial shock and had relaxed enough to start enjoying the feelings, she was well on her way to a huge orgasm. I continued to work my tongue inside of her sweet tasting cunt while the fingers of one hand pried her lower lips open to give my tongue even better access. At the same time I slipped one hand out from between her legs and reached across the bed to the night stand. My hand worked its way into my case there and extracted the tube of cream that was near the top. Without missing a lick I removed the cap and squeezed a generous portion of the cherry flavored cream onto my finger. Then that finger eased back into position and began applying the cream in and around her tight rosebud with that finger finding its way deep inside of her ass and working the cream all around the inside of her opening too. Now it was time to get her relaxed while the desensitizing cream worked its magic. I renewed my oral assault on her pussy and started licking her with a fervor. My tongue flicked her clit and I dove in and drove my tongue deep into her hot box trying unsuccessfully to reach her cervix inside. Polly was thrashing around on the bed now moaning and humping against my face. Her hands had come down and she had a hold of my hair pulling me deeper into her as she wreathed and climbed her way to a heart-stopping orgasm. Then it was upon her. Her legs went stiff and then flexed as she grabbed my head even tighter and came hard. I continued to use my tongue around the inside of her womanhood doing everything I knew she liked to make this a huge orgasm. When her climax finally stopped and she was having those little `after-shocks' that a woman can have after a really good orgasm, I slipped out from between her legs and looked up at her. Gawd she was beautiful. There is nothing prettier than a woman with that glow about her that comes from a experiencing a huge climax. I knew I couldn't wait too long. My little friend was not interested in waiting either as her danced and throbbed below. I carefully rolled Pollyanna over onto her stomach and let her legs slip off the end of the bed. Her wonderful ass was poised there in front of me just begging to be fucked. I knew that while Pollyanna was still off in Nirvana from the huge climax she had just had, I had a better chance of getting into her lovely ass without hurting her. Quickly I reached into my bag again and got one of my lubricated condoms. I was sure this would make me slipperier and less likely to cause pain as I went in. With that on, I lined up behind her and took myself in hand. Using my hand to guide my throbbing meat stick, I carefully lined the head up with the entrance to Polly's almost-virgin asshole. I pushed slightly and felt the resistance there as her asshole puckered and spread trying to accommodate my girth. That cream must have been working because I soon felt the head of my dick slip through and into her dark tunnel without causing her to cry out. I stopped long enough to calm myself. I wanted to drive into this woman and use her hard and it took all of my willpower not to do just that. She knew what was happening and by now the glow and wonderful feelings of her orgasm were being replaced by the feeling of fullness as I pushed slightly deeper into her behind. Slowly and ever so carefully I worked my love-rod deeper into poor Pollyanna as I felt her butt loosen its tight grip and relax ever so slightly. When I bottomed out and felt my pubic hairs against the cheeks of her ass, I stopped and stayed motionless for several moments while Polly adjusted to the feeling of my hard cock deep in her nether region. Then I pulled back slowly feeling the exquisite sensation of her asshole gripping my cock like it didn't want it to leave. With only the head still inside, I started back down pushing more and more of myself into her bottom. This I repeated at least ten times going as slowly as I could force myself to do and each time allowing poor Polly to adjust to the sensations. After ten (maybe twelve or fifteen?) times I received a wonderful surprise. As I was slowly pushing back down into Polly I felt her raise her hips slightly and push back into me. Then she turned her head to one side and asked to go a little faster please. I was more than willing to accommodate this desire and I started to friction in and out of her beautiful ass faster and then faster still. I was also feeling her humping up against my driving pecker as she tried to push her ass up and get my meat ever deeper into her tight butt. Now more than ever I wanted to let loose and just fuck her tight ass without mercy. And now more than ever I forced myself to control my speed and not hurt her. I was so wrapped up in what I was doing that I didn't hear her at first when she asked me to cum. Then she said it again. "I want you to cum in my ass. Please cum inside my ass and fill me with your hot spunk." That was it. I couldn't wait anymore. I started fucking her beautiful ass for all I was worth. Pollyanna grunted a couple of times and shifted her position slightly as I increased my speed and drove ever harder into her tender brown hole. I was so close but I wanted to hold out longer. I wanted to feel that wonderful tight sphincter as it opened and closed around my throbbing cock. I wanted this ass-fuck to last forever. My seed was rising up from deep in my balls. I felt it as it pushed upward and started its journey and I felt it as it rushed up my shaft. Then I felt it as it streamed out of the head and shot deep into her hot brown tunnel coating the sides with my cum. I kept fucking her ass and driving my cock into her as my need was fulfilled and a second short spurt of man-cum followed the first into Polly's sore abused ass. As my orgasm finished and I spun back down to reality, I realized that Polly was lying there smiling at me. She hadn't cum or had any kind of an orgasm; that would be too much to ask from her on the first time, but she did seem to have enjoyed the anal sex and that smile told me that she might be willing to do this again too! My muscles seemed to give out and I collapsed on the bed alongside of her with only enough strength to roll over and hold her in my arms. In moments I was dozing off. I vaguely remember the soft touch of Pollyanna's hand in a washcloth a few minutes later as she removed the condom and washed me off. I awoke again just before noon to the sounds of Pollyanna busy at her computer. She had a string of songs playing on the computer `jukebox' and was working humming along to the music. I noted that she was dressed this time so I quickly donned my clean clothes from my overnight bag and walked out into the dining room where her computer sits. When she saw me she smiled and asked if the `old lazy bones' had gotten a nice nap. I assured her that I definitely had and I was now famished. She stopped what she was doing and said she'd make something right away. As she got up to go to the kitchen, I stopped her, wrapped my arms around that body that had given me such pleasure and smiled at her. I said that since we were both dressed, why didn't we just go out? She thought that was a marvelous idea and skipped into her bathroom to brush her hair and add some morning make-up. While Polly was doing this, I thought about where we should go for lunch. I had wanted to take her someplace special but this didn't seem like the right time for that somehow. When she came back into the room a few minutes later she had this wonderful smile on her face that absolutely melted my heart. I decided right then that I would do almost anything for this woman if I could just keep seeing her somehow. We headed out in her car with the windows down and the warm breeze blowing in our faces. I told her to pick a place and she surprised me by driving into the local drive-in restaurant. We parked away from the other cars and ordered burgers, fries and cokes like a couple of teenagers. We talked about everything there in that burger joint parking lot. I asked for her feelings about me and was she glad I had come this weekend. She smiled in that special way she has and the twinkle in her eyes gave me my answer before she opened her mouth. I also asked her if I had done anything to upset her or make her afraid. I was concerned about this since I remembered becoming quite aggressive a couple of times when I was turned on and fucking her. She assured me that I was fine, she was fine and she had enjoyed being the object of my lust and desires. As we ate I decided to ask her about something else I needed to know. I hedged a little bit but finally came right out and asked her if she had enjoyed the anal sex. She confided that she was pretty nervous about that at first and that she was glad that we had gotten her so excited and made her cum before we tried it. Now she felt that she really didn't mind the anal sex so much and wasn't nearly as scared of it because we did it that way. In fact she thought that maybe we should try it again before I left for my plane tomorrow! The rest of the conversation centered around our thoughts and desires for the future. Needless to say, we went back to her house that afternoon and continued where we had left off. For the rest of that day and night and into the next morning I spent every waking minute with lovely Pollyanna in my arms. We made love in the kitchen by the stove and in the dining room with her lying on her table and me standing at the end. I had her on her knees in the living room while I watched the Weather Channel that night. She sucked and licked and loved my hard cock while I tried to see what flying would be like Tuesday morning. Of course we did it in every position, in every hole and in every way we could think of in her bed that night. Day Four: Monday morning: Monday morning came around all too soon for me. I rose and snuck into the bathroom without waking Polly. Then I made a quick trip to the kitchen and started some coffee for us. When I returned to the bedroom I stopped for moment and looked down on this lady that had changed my life so much over the past three days. She was asleep with her long hair around her face and the soft smile of an angel on her lips. I knew we didn't have a lot of time since she had to get to work sometime this morning. I leaned down and kissed her softly. Her eyes fluttered open and she smiled up at me with a look that felt like someone had just turned on the sunshine in my life. Then she said, "Good morning darling" with her soft voice that made me want to melt. I slipped my arms around her and kissed her as I held her tight. Our kiss turned passionate and soon I felt my desire rising like a volcano in my soul. I rolled onto the bed beside this lovely lady and took her in my arms while I continued to kiss her sweet soft lips. I wanted her again. I was fighting it because I knew she needed to get to work, but I wanted her so bad. My desire must have been quite apparent as my little friend rose up to greet her too. I kissed her and then started to pull away saying that I knew she needed to get going or she'd be late for work. With an impish smile she asked me what time I had to leave to get back to my plane and pick up the boss. I told her that I could leave anytime before four and I'd be just fine. Her smile grew even bigger as she reached over alongside the bed and picked up her phone. She told me that her assistant could handle things today and she was just going to take the day off to see how he would do with out her! Footnote: I returned to my friend's house and spent the night there having a couple of drinks and talking about old times together. He noted that I seemed distracted and I told him I was concerned about the weather for the trip home. In fact I had called the weather service and gotten a weather briefing that I could expect a few clouds and no turbulence at my chosen altitude going West. That poor weather briefer had to repeat parts of his briefing a couple of times because my mind was elsewhere. The next morning I did my pre-flight inspection twice to be sure I hadn't missed anything and chastised myself for not being 100% into my job. I used the short flight back to pick up my boss and his party to become a professional pilot again. When the boss climbed in and I swung the door closed he asked if I had a good weekend or was I bored to tears. I assured him that my weekend was just fine and I wasn't bored at all. In fact I had visited an old friend not too far away and made a new friend too. Little did he know just how special that new friend was to me!