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The Pleasant Surprise
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The Pleasant Surprise The Pleasant Surprise With the sun shining through the leaves of the tree’s, the shade patterns on my body kept changing as I jogged through the forest along the paved pathway that snakes through my neighbourhood near home. The leaves had just begun to change colors, but most had not fallen yet leaving only a littering of leaves scattered on the ground. Most days I would pass the occasional fellow jogger but today I had not seen anyone on the path. Maybe it was because it was a little cooler than normal, and most joggers had not yet acclimatized to the cooler temperatures of early October. About ten minutes into my jog, 250 calories according to my Apple watch, I started approaching what appeared to be a very attractive woman walking in the same direction as I was jogging. She was wearing a very tight black skirt that came down to just above her knees with a light red jacket that ended at her waist and high heels. She looked like she was dressed for the office and a little out of place along the pathway, as you normally only saw people dressed for a jog or to walk their dog. Approaching her from behind, I noticed she had a very cute butt with a sexy wiggle that drew my attention. I could not take my eyes off her butt cheeks as they swayed left then right in a hypnotic sensual repetition. Just before I was going to pass her on the pathway she stepped on a patch of fallen leaves, and her leg slipped out from underneath her causing a traumatic tumble to the ground. I immediately rushed to her aid and knelt beside her, “Are you ok” I said. “I am not sure,” she replied, “I think I might of sprained my ankle.” I looked at her ankle and saw right away that it was already starting to swell. On the ground near her foot lay her high heel shoe with the heel broken off. “This was likely the cause of your tumble.” I said showing her the broken heel. She looked disappointingly at the shoe and said, “I think your right.” “Can you walk?” I said “I don’t know, let me try” Holding my hand out I helped her to her feet. Letting her go she almost immediately tumbled back to the ground but thanks to my quick reflexes I caught her and prevented another fall. Realizing it could be serious I asked “Would you like me to call an ambulance.” “No, I live just a few blocks from here, I think I can make it home. Can you help me?” “Of course,” I assured her. I held her hand helping her stand. She put her arm around my neck and I put my arm around her thin waist, very much enjoying the feeling of my arm around her feminine body. “Hi, my name is Jenny by the way” “Hi, I’m Rick” “Thank you so much for helping me!” “How could I not help a beautiful damsel in distress,” I said smiling at her. She smiled sweetly back at me, and keeping the weight off her injured foot with her arm around my neck, we began to hobble slowly back to her house. On the way, she explained that her car was in the shop for repair so she was forced to take the bus to work and the forest path was the quickest route to the bus stop. As we chatted, she informed me she was an office manager for a small firm downtown and she was worried because she would likely need to take a few days off to let her ankle heal, and this was the busiest time of year. I replied it was probably a good idea to take a few days off and not to worry. As we hobbled together down the path, we came to a large puddle completely covering the path. It had been raining the last few days and the ground was thoroughly soaked so these puddles had not dried yet. As Jenny was carrying her broken shoe, I offered to carry her over the rather deep puddle so as to keep her feet dry. She laughed and said, “How I could I say no to a big strong man offering to carry me?” I smiled, and she put both her arms around my neck and I scooped up her sexy legs and carried her across the puddle laying her down on the other side, both feet dry. Our eyes had met as I was carrying her and I am pretty sure I could tell there was a moment of attraction. She had the most beautiful eyes and I must admit, feeling her sexy body in my arms was somewhat arousing. After about 30 minutes of hobbling we finally managed to make it back to her house. Unlocking the door she turned to me and said, “Thank you so much for helping me today, I have no idea what I would have done without you.” She reached up and kissed me on the cheek. Smiling I joked, “just another everyday event for your friendly neighbourhood super hero mam!” She laughed and said, “one moment.” She hobbled into the house and moments later returned with a business card, “If you would ever like to get together here’s my card, she said, my cell number is on the back.” “Thanks, I’ll call you.” She smiled and kissed me on the cheek one more time. For the next two days I couldn’t think of much else, Jenny’s sexy body was on my mind! Her cute ass and sexy wiggle kept dominating my thoughts, I needed to call her. We chatted for some time on the phone and finally she asked if I would like to come over for a drink, an offer I accepted immediately! Jenny’s place was not to far from mine, so I walked over that evening. Waiting on the doorstep after ringing the doorbell, I was picturing what outfit Jenny might have on. When the door opened wide my jaw almost dropped. Jenny was standing there in a skin tight black dress with a short hem line and fish net stockings that accentuated her long dancer like legs. Her long dark hair was flowing over her shoulders and she wore a black choker that added to her sexual mystique. Her breasts were small but very perky and If I had ever pictured the love goddess Aphrodite, Jenny was orders of magnitude sexier. I instantly felt my cock start to harden! Jenny led me to the living room where we sat on the couch together. The living room was spacious and the couch faced the fireplace which was snapping and crackling as it burned. Jenny had lowered the lights which made the warm embers from the fireplace the main source of light bathing the room in its romantic glow. She poured us both a glass of wine, and as we sipped wine she filled me in on how she had gone to the doctor later that day of her tumble, and that the doctor had said it was just a sprain. He had advised her to stay off it for a few days until it healed and wrapped her ankle in a tensor bandage. Still chatting and laughing Jenny suddenly stopped and smiled at me. With a sexy knowing smile on her face she took the wine glass from my hand and placed it on the antique coffee table in front of us. Looking into my eyes she said, “I never thanked you properly for so gallantly coming to my assistance.” She looked into my eyes with a penetrating sexual stare and leaned in, kissing my lips so softly and passionately I thought I was going to orgasm right there. She pushed me back on the couch still kissing me, and with her body on top of me, her tongue penetrated my lips to begin playing with my tongue. Kissing her as passionately as I could, I wrapped my arms around her slim body and I felt the nipples of her very small breasts pressing against my chest. I ran my fingers down her back and caressed her very shapely bum holding her as tightly as I could while pushing my cock against her. As she started to grind her groin against my cock I could feel a bulge in her groin. I was a little confused and became concerned. Noticing my sudden change, Jenny stopped and questioned, “Is everything alright?” “I am not sure, I said hesitantly, I felt a bulge in your panties.” Jenny smiled, “I am sorry, I suppose I should have told you, I’m a transsexual, that’s my cock. I just thought you knew. Are you ok?” Wow, a transsexual. I had had many fantasies about being with a transsexual but those were just fantasies. Suddenly finding myself with one caught me off guard. Her words, “I just thought you knew,” echoed back to me. Thought I knew? How could I know, you looked just like a beautiful woman! Was I ready for this, I had never been with anyone other than a woman? “Would you like me to stop,” Jenny asked in a very soft tone which brought me back from my thoughts. This girl was beautiful and I was very much attracted to her. No, I thought, no I don’t want her to stop and I told her so. “No! Please forgive me, it just kind of caught me off guard.” Jenny smiled at me and bent down and kissed me with a passion that penetrated my heart. “Have you ever been with a trans girl?” Jenny asked. “No, but I have thought about it many times.” “well were going to make tonight very special.” she whispered. With that she bent down and kissed my lips softly. The softness of her lips against mine will forever be ingrained in my memory, I don’t ever recall being kissed the way Jenny kissed me. It was incredible. Jenny started undoing the buttons of my shirt and kissed my chest after each button was undone. After releasing the last button, she pulled my shirt wide open and began to kiss my nipples. Her tongue licking, and her lips sucking on my nipples felt so sensual it was making my cock wet, and I knew when Jenny finally placed her fingers around my cock she was going to find a very wet sticky shaft, and a mushroom head bubbling precum. She kissed her way down my chest, each kiss tormenting my cock aching for her lips. She finally reached my belt which she quickly unbuckled, and after unzipping my Dockers, she pulled them off my body. Jenny stood there with my pants in her hands and starred with a smile at my skimpy white underwear tightly cupping a huge bugle with a large wet spot where the tip of my cock came to rest. She dropped my pants and knelt down between my legs. She erotically traced the outline of my cock through the material and sensually caressed the wet spot of my underwear with her fingers, licking them periodically to taste my precum. Pulling my underwear down with her teeth allowed my very hard cock to spring out like a Jack in the box, and Jenny wrapped her fingers around my hard shaft, stroking me several times before lowering her soft red lips to my wanting cock. I found being completely naked on the couch with Jenny fully dressed very arousing which only increased the precum bubbling from my cock, and being licked clean by Jenny’s tongue. Her lips wrapped around my mushroom head, and she slid her lips slowly down my slippery penis to the base of my cock, massaging my balls as she started to bob on my cock. I was getting close to orgasm which I think Jenny realized because she stopped, stood up and smiled at me with that sexy smile that had originally melted my heart. I looked at her still in her skin tight black dress, she really was a beautiful girl, and I found myself quite anxious to see her beautiful cock that was now preeminent in my mind. She reached behind her back and slowly unzipped her dress as I watched her with great anticipation. She pushed the dress off each shoulder and let it fall to the floor. She remained standing as I marvelled at her beautiful body covered only by white lacy matching bra and panties and a white garter holding up her stockings. I could see the tip of her hard cock peaking out of the top of her panties. It was beautiful, I thought, and I knew I wanted to wrap my lips around it. Still smiling, she straddled my hips and started to grind her hard cock against mine. I could feel her shaft, warm and wet, sliding against mine mixing our precum together in the process. While grinding our cocks together she bent down and kissed me. I love kissing, and I knew I could never get enough of Jenny kissing me. She kissed with such passion and sensuality it was unequalled, at least by my experience. Jenny slipped off her panties and straddled my hips again, this time sliding my very wet slippery cock between her bum cheeks. The feeling was so sensual and Jenny, starting to moan softly, wrapped her fingers around my cock and guided it to her moist ass<b> pussy. </font></b>She placed it against her hole, and the mushroom head coated in precum, through a combination of my thrusting slowly and Jenny pushing back, quite gradually penetrated her tight warm hole causing her to moan, “yessssss.” I slowly pulled out and repeated the process penetrating a little deeper as Jenny was moaning, “mmmmmm, yes baby.” Again, I repeated pulling out and pushing even deeper into her, and again she moaned, “mmmmmm, yes baby.” With every repetition I penetrated a little further and stretched her tight<b> pussy </font></b>a little more until I was fully inside her with the base off my cock nestled up against her cheeks. Slowly I started thrusting back and forth with Jenny meeting my every thrust in perfect timing as she bounced up and down. Very gradually our pace quickened until we were pumping each other like a steam engine, and I had Jenny moaning loudly. I was so turned on by Jenny and I was approaching orgasm so I said, “Baby your going to make me cum” “Yes, yes, she said, cum in me, cum in me, cum in me.” With one final powerful thrust into her<b> pussy </font></b>I moaned loudly and shot wave after wave of hot semen into Jenny. She collapsed on my body, and with my cock still in her, the last few cock spasms made sure all my cum was inside Jenny’s<b> pussy. </font></b>Holding her tight I kissed her and said, “your beautiful and amazing” “So are you,” she said smiling at me. Holding her tightly in my arms I noticed her hard cock trapped between our bodies, so I smiled at her and turned her over on her back. She smiled back at me anticipating what was going to happen next. I spread her smooth silky legs for better access, and I lowered my lips to her still hard wet cock. I could taste her precum as my lips slide down to the base of her cock. The sensation of a cock on my tongue and lips was one I had not experienced before but it felt very sensual and enjoyable. I slowly raised my lips back up her shaft and swirled my tongue around her mushroom head. I knew I was giving good head when Jenny moaned softly, “that’s it baby. You feel wonderful,” Not being able to answer, for obvious reasons, I continued to slide my lips up and down her shaft picking up speed as Jenny’s sweet moans inspired me on. Bobbing up and down on her cock felt so good and I wanted her to cum. Moaning loudly jenny warned me, “I am going to cum Rick.” Not stopping to let her cock out of my mouth, I felt her cock start to throb as my lips were sliding up and down. Realizing I wanted to taste her, she thrust her cock deep down my throat moaning as I felt her hot sperm fill my mouth in an explosive ejaculation. Her cum was hot and sweet on my tongue and I surprised myself how much I enjoyed it. I cuddled with Jenny holding her tight while we kissed. Her tongue probing mine for the sweet cum she had gifted me. This was all a new experience for me and Jenny had indeed made it memorable and sweet. Here it is six months later and were still seeing each other, who would of thought this would all come about from a pleasant surprise. |
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