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Long Lost Friend By Teri It had been a long week at work and I was looking forward to just spending a lazy weekend at home. The bachelor life was pretty nice, I had the freedom to spend my time the way that I wanted and this weekend was going to be movies, football, beer and my couch! My name is Jack Mehoffer and I am 26 years old. I work as a financial consultant in Chicago and live in a town house by myself just outside of the city. I find my job often times pretty mundane, but since I am the youngest guy in the office, all the shit rolls down hill. I basically get the accounts and jobs that the other more seasoned veterans don't want. By the end of the week I am usually pretty run down and look forward to spending some time at home, only worrying about if I have enough food and beer to make it through the weekend. So, on Friday night, I got home about 6, changed from my power suit into blue jeans and t-shirt and popped a frozen pizza into the oven. I sat down to watch the evening news and opened my first beer when the phone rang. "Hello." I answered, not recognizing the phone number from the caller ID. "Jack, it's Terry Lynch, How have you been?" A perplexed look came over my face as I remembered this guy from back in high school. Why would he be calling me? "Hi Terry, this is an unexpected surprise, what has it been almost 9 years since we have seen or talked to each other? What's going on?" "Well Jack, I am in town and had heard that you were living here from some old high school friends. I am actually at the airport and my flight has been cancelled. I took a chance, looked in the white pages and found your number. I thought maybe we could have a drink or something? Unless, you had other plans?" I had not seen Terry in quite awhile and felt badly that his flight was cancelled; it would be nice to see someone from my younger days. We were never really close, but we did hang with the same group of friends. He had always been a quiet type, did not date much, but was at all of the same parties. It might be fun to get together and reminisce. "I have an even better idea, since your flight is cancelled, how about you come on over to my place, I have a pizza in the oven and some beer in the fridge. We could sit, relax and make up stories about back in the day?" I said. "I live about 5 miles from the airport, why don't you grab a cab and come over?" After some half hearted arguing about putting me out, he agreed to catch a cab and said he would see me in about a half an hour. Well, my plans had changed, but I was looking forward to seeing Terry again. I jumped up and tried to straighten up my place before he arrived. I must admit that I do keep my place neat, but I wanted it to look extra nice so Terry would tell the people back home that I was living and doing well. The doorbell rang at just after 7pm. I opened it to see a smiling face that I had not seen in quite some time. Terry still looked like he had back in school. He stood about 5'8 about the same as my height, slightly built, also like me, dark black hair as compared to my light brown, and it was slightly longer than I remembered, but he still had a big smile on his face. We shook hands and I helped him carry a couple of bags into my house. He was also wearing a backpack, which I assumed was used as a carry on item for the airplane. I grabbed Terry a beer and another for myself and pulled the pizza from the oven. We sat and talked and laughed at old stories over dinner. He asked about my current situation and I told him about my job and that I was still single but "on the prowl", just having a hard time getting out after working so many hours in my job. He listened intently and smiled at me with a gleam in his eye. "What is so funny?" I asked. He just thought that the situation I was in sounded very familiar, that he was basically doing the same, but only in a smaller town outside of Boston. I found out that his flight was not until 10 am the next morning and offered up my spare bedroom for the night. He reluctantly agreed, although I think he was happy to be able to spend some more time with me. I showed him the room and let him get some of his stuff unpacked while I went back down to clean up the dinner table. "I am going to take a quick shower and get out of these clothes and into something more comfortable, if that is okay with you?" he yelled down the stairs. " "Go ahead and make yourself right at home, I will dig around and see if I can find a movie for us to watch after you are done." I heard him enter the upstairs bathroom and heard the shower start up. I thought to myself that it was nice to have someone over as I looked through my movie collection. I sat down and daydreamed back to high school and tried to remember if I had ever seen Terry with a girl, besides the times we all went out as a group. He was in some of my classes, but he was always very quiet and seemed to keep to himself. But hey, everyone is a little strange while going through puberty right? I myself was not exactly a chick magnet in high school and even nowadays my door is not getting beat down by women either. It sure would be nice to have a woman around, who understood my wants and desires and was devoted to me, and I to her. I heard the shower go off and then heard the familiar sound of a blow dryer and thought that Terry would probably be back down soon. I would have to let him choose the movie because I had seen all of the ones I had, and besides that, he was my guest. I heard the bathroom door open and Terry yelled down, "Jack, could you please grab my backpack from the kitchen and bring it up to me? I seem to have left it down stairs." "Sure, be right up." I found the backpack and headed up the stairs, knocked on the door and handed it through the slightly ajar door. "Thanks, I will be down in about 15 minutes, you have any wine in this bachelor pad?" he asked through the door. I thought I did and told him I would go open the bottle and would be down in the living room waiting for him. I went to the kitchen and saw that I had a bottle of Merlot; I guess that would have to do because it was all that I had. I opened the bottle to let it breathe, and in the mean time popped open another beer for myself. I have always liked beer better anyway. I found a couple of wine glasses, poured a couple of glasses and set them on the kitchen table. I grabbed my beer and went back to watch the TV while I waited for Terry to come downstairs. I looked at my watch and realized it had been over a half an hour since I had brought Terry his backpack. I was wondering what was taking him so long and hoped that he had found whatever he needed to make himself comfortable. I turned to yell up the stairs to him, and when I did, I noticed a shadow from the corner of my eye. Looking closer, it became apparent that Terry had come down stairs and was standing in the shadows of the dining room. I could barely make him out. "Man, you scared me for second, I never heard you come down the stairs. What are you doing over there? I can barely see you. Come on, I have the wine poured for us in the kitchen." I said as I got up from the couch. "Jack, please stay where you are for a second. I wanted to show you something and I was afraid of what you might say or do, so please just stay put while I show you." This was getting weird, what could make him so nervous that he was hiding in the shadows and was afraid to show me? "I wanted you to meet Teri." he said as he stepped form the shadow. I laughed and said "I have known Terry for a long time..." the words stopped coming and my mouth just hung open... "Holy shit, Terry? Is that you?" I asked dumbfounded. Standing before me was a beautiful woman (at least it looked that way). He/she was dressed in a blue satin knee length dress that was gathered in a high waist that showed off a pair of well rounded breasts. Her legs were encased in nude colored nylons and she had black patent leather pumps on with 3 or 4 inch heels. I looked her up and down, makeup was flawless, shoulder length black hair styled carefully. I was mute! "Yes it is me, but it is Teri with an "i" when I am dressed like this. I was nervous about how you would react to seeing me this way and did not want to offend you or your hospitality. This is the way I am most comfortable and I want to be comfortable around you. Is the offer of the glass of wine still open?" She said with a smile. I have to admit, I was kind of weirded out, but I just nodded and moved towards the kitchen. I did not for one second take my eyes off of "her." I picked up the two glasses and handed one to her. I noticed that she did in fact have delicate hands and her nails were now polished a bright red, which also matched her lips. I still could not get myself to talk. She took her glass and walked seductively to the living room and motioned for me to join her on the couch. "Jack, please try to relax and I will try to explain what you see before you. Ever since we were kids, I have never felt like I was one of the guys. You might remember that I was a pretty shy kid; I did okay in groups but never was very outgoing? I have been secretly dressing like this since I was very young. I knew that one day; I would eventually live like this full time. It was the one thought that kept me going over the years. I am now able to be who and what I want to be without the fear of what others may think of me. I always thought that if anyone from my high school days would understand, it would be you. Am I making any sense to you at all?" I was still in a daze, here was my old high school friend, sitting on my couch next to me and he is dressed like, smelling like and looking like a hot chick. My mind was going in circles and I could feel my arousal. I was hoping that Teri would not notice that I was sporting wood as I sat almost drooling beside her. How could I feel these feelings? I knew what she was under the dress and knew that I was a truly hetero guy. I knew I had to say something, but did not want to make a complete ass of myself. "You are beautiful, I can't believe how great and natural you look" I said, surprising even myself. Her eyes lit up and a huge smile came across her face. She placed her hand on my knee and said "Jack, you are awesome! I always knew you would be an understanding person and I guess I was right." Her hand continued to rub my knee and I felt it gradually moving towards my crotch. She continued to stare into my eyes, looking to see if this was okay with me. Boy was it! She leaned slightly towards me, while keeping direct eye contact and I knew what was coming. I tilted my head slightly and our lips met. Tentatively at first, we gently explored each others lips, gradually escalating to using our tongues, getting hotter by the second. I felt as if I would cum at any time. Teri worked her hand up to my zipper and I lifted my hips to allow for easier removal of my pants. I reached up and put my arm around her and allowed myself a quick feel of her breasts, and with my other hand I fondled her nylon clad leg. Mixed emotions ran through my head, but the feelings were just too good to stop. We did not break the kiss as we writhed on the couch. I felt under her skirt and realized that she was wearing a slip and I felt the clasps of a garter belt that was holding up her stockings. My hand continued to rub against her satin and nylon covered legs. As I worked my hand higher, I felt the satin of her panties and as my hand moved across the front of the panties, she let out a slight moan. She broke the kiss and pulled slightly away from me, looked at me quizzically and asked "Jack, are you sure you are ready for this?" I don't want you to feel uncomfortable or to think you have to do anything you don't want to do." I stood up, removed my belt, dropped my pants and underwear, my 7 inch cock was standing at attention. "Teri, does this show you how much I want you? I have never been hornier in my life, and I would like to help you remove your dress too if that is okay?" She quickly stood, but not before leaning forward and giving my cock a quick lick. She turned so I would have access to her zipper, and I gently lowered it for her and she stepped from her dress. I helped her remove her half slip and there she stood in her bra, panties, garter belt, stockings and pumps. She was truly a vision of femininity and I felt like a very lucky man. She placed her hands on my shoulder and pushed me gently back to a sitting position on the couch, lowered herself to her knees and leaned towards my awaiting cock. "I have waited for a long time to finally get to do this to you" she said as she took my cock into her mouth. It was apparent that she knew what she was doing; she expertly took my entire seven inches in without gagging and began to move slowly up and down. I knew that I was going to cum very quickly and let her know I was close. Instead of slowing down, she increased her tempo, I continued to buck my hips and shot a load into her throat. She never lost a beat, swallowing my load and licking my cock like it was a lollipop. Not a single drop was missed and she made damn sure of it! I felt her release my cock and I opened my eyes to see her staring at me with a wry grin. "You tasted wonderful, I hope you can recover soon because I have some other places I would like you visit besides my mouth" she said as she slipped on to the couch beside me. "I just need a few minutes to recover and then I am all yours. I think, no I am sure, that this was the best blow job I have ever received in my life. I don't know how to thank you" I said as I wrapped my arms around her. We kissed and I could taste myself in her mouth. Although it was not unpleasant, it was a new experience for me, one I thought I could learn to like. "I know how you can thank me, but first you need to build your strength back up. Why don't you freshen up our drinks and I need to go freshen myself up too" she said. I watched as she got up from the couch, seductively looked over her shoulder at me and asked "do you like what you see?", giggled and headed upstairs to the bathroom to freshen up. I was not sure what "freshening up" meant, but I was so infatuated with her that whatever she said was fine with me. I got up and walked into the kitchen to refill our glasses of wine and noticed the lipstick imprint on her glass. That was something that my house had not seen in quite a while. I smiled and headed back to the couch, my erection standing out eager in anticipation of what may lay ahead. After a few moments I heard footsteps and turned in time to see her coming back down the stairs. She had changed into a baby doll nightie in black satin with matching string bikini panties. I did not think my cock could get any harder. I stood up to meet her and she smiled and reached for my cock. "Well, it looks like someone is happy to see me" and then she leaned in for another kiss. As our bodies pressed together, I could feel her hardness pressing against the satin of her panties and I reached down to free her cock from the satin confines. "Time for me to make you feel good, I am new at this but am a quick learner, I can see you are happy to see me too" I said as I freed her cock from the panties. This was the first cock, other than my own, that I ever touched. It was almost hot to the touch; she was cut and seemed to be about the same size as my own seven inches. The precum made her cock slippery in my hand and I tried to concentrate on what I knew felt good to me. She seemed to be enjoying it, but then gently pushed my hand away. "I want us both to feel good and I know just how to do it" she said as she took me by the hand and lead me up the stairs to my bedroom. When we entered the bedroom, she quickly stepped out of her panties and got onto the bed on all fours. She looked over her shoulder at me and gave me "the look." That was all I needed and quickly joined her. This was another new experience, I had never had anal before, but was anxious to learn. I kneeled behind her and she helped guide my cock to her ass. Now I knew what she meant by freshen up, her ass was already lubricated and ready! I could feel the head of my cock enter her with slight resistance, heard her moan slightly. I was afraid that I was hurting her, but she quickly let me know she was fine and wanted me deep inside of her. I was more than happy to oblige and applied pressure until my cock slid in to the hilt. I could feel my balls against her ass cheeks. Her ass was tighter and warmer than any other place my cock had ever been and I let out a slight moan as I grew accustomed to this new experience. She reached behind me, took my hand and brought it around to her own cock. Now I realized what she had meant about both of us feeling good. I began to slowly rub up and down on her cock while at the same time getting into a rhythm of pistoning in and out of her ass. It all felt too good and I quickly came once again into her ass. "I'm sorry Teri, it felt so good that I could not control myself" I said as I started to go soft and slip out of her love hole. We adjusted our positions so we were spooning on our sides, my soft cock against her ass. I put my arm around her and continued to rub her cock with my hand, and felt her shiver in delight. I decided that since I was already in for an inch, I might as well go for it all. I removed my arm from around her and positioned myself on my knees between her legs. "Jack, please don't do anything you don't feel comfortable doing" she said. Without a word, I slowly lowered my lips to her waiting cock, it was already wet from her pre-cum and it easily slipped into my mouth. I had just crossed a major boundary, but had a feeling that there were still more to cross tonight. So far tonight I had found out an old friend was a cross dresser, allowed her to suck my cock and fucked her in the ass. Now I was on my knees sucking a cock for the first time ever. As I worked on pleasuring Teri, I began to overcome the metal blocks or inhibitions of my actions and began to enjoy myself. I could tell that I must be doing this the right way because she was moaning and telling me that she was close. I continued to slurp and then reached up and inserted a finger into her well lubricated ass and that must have done the trick. She began to buck wildly and to spurt her spunk into my mouth. I applied suction and did not take my mouth away from her love pole, swallowing it all. The taste was similar to what she had shared with me earlier and was not at all unpleasant. After I was sure that I had swallowed and milked out every drop, I let her cock pop from my mouth and lay back down beside her. "Wow, talk about orgasms! That was the best for me, ever!" She said with a grin and leaned over to kiss me gently. She was propped up on her elbow and asked me what was going on in my mind at that moment. "I will be totally honest and tell you that I was very nervous at first, but now feel like this is the most natural thing that could have happened. I can't think of a nicer way to spend my Friday night, with a beautiful woman and making love. This is not what I would consider my typical night of love making, but it is definitely the best ever!" I said with a smile. "How about a shower?" she asked and I readily agreed. After our shower and another new experience for me, doing Teri in the ass under the shower head, we dried off and she put her night gown back on. I threw on a pair of boxers and we headed back downstairs for more wine. I knew that this relationship was unorthodox, but I did not want for it to end anytime soon. "Teri, I know that you have a flight tomorrow, but are there any pressing reason why you have to leave so soon? I would really love it if we could spend some more time together. Maybe you could change to a Sunday flight or maybe even later?" I asked her or more realistically pleaded with her. She said that she could look into other flight arrangements, so I showed her to the spare room that I used as a home office and let her sit down and connect to the Internet. "While you are looking into it, I will get us another drink" I said as I left the room. "Well, I have changed my flight; I now leave at 5pm on Sunday. So what would you like to do for the rest of the weekend?" She asked with a gleam in her eye. I think she had the same idea as I did, but I had no idea where I would get the stamina to make it through two more days, but I was sure willing to give it a try! "I am pretty sure we can think of something to keep us busy. I know that I need to show you off, so maybe tomorrow I will take you out to a nice dinner and a movie. I can show you around town during the day. But I have to tell you it will be hard to keep my hands off of you!" As I stood there with my boxers tenting out and a sheepish grin on my face, a yawn shook my entire body. Teri laughed and said she knew that she would have an effect on me but did not realize that she would put me to sleep! I begged forgiveness and told her that she had worn me out, but promised to be more than ready for our weekend together. She came over to me and gave me a hug, "thank you for being so special, why don't we go to bed and we can pick up where we left off tomorrow?" She took me by the hand and led me back upstairs, and I admired her ass as she lead me up the stairs, I knew that I wanted her one more time before we went to sleep. This time, we pulled back the covers and got between the sheets. We snuggled and all of a sudden I realized how selfish I had been tonight. I had been concentrating on my own pleasure by having three orgasms and totally neglected Teri! "I am so sorry for the way I treated you tonight, I just realized that I was pretty selfish with you and did not take care of your needs" I said. She sat bolt upright, looked at me and said "Jack, I don't see it that way at all. We enjoyed it equally, but it is sweet of you to be looking out for my pleasure too. I am hoping that by the end of the weekend, we will open more new horizons for you and me too" and she leaned over, kissed me, smiled and said goodnight. We snuggled together, this time she was spooning me and I could feel her satin covered cock pressing against the crack of my ass. What exactly did she mean by new horizons????? I awoke to a nice feeling between my legs and realized that my cock was being sucked. I looked between my legs and saw Teri going to town. What a way to wake up in the morning! I tried to sit up but she would have none of that and kept to the task. I grabbed at her hips to try to get at her cock and motioned for her to come around into a sixty nine. Apparently she was just as horny as I was because within minutes we were both shooting into each other's mouths. "Good morning lover" she said with a smile and a gentle kiss. I returned the kiss greedily and began to softly rub the satin material of her nightgown against her nipples. I could tell that her nipples were enlarged and that she enjoyed having them massaged. "I think I have found another area to explore on your body, you seem to be very sensitive around your nipples, would you mind if I sucked on them?" I asked innocently. She sat up and pulled her nightgown over head, threw it on the floor and said "I thought you would never ask! Please feel free to experiment with me in any way that you want as long as it is not painful." She leaned forward and put her nipple to my mouth and I eagerly accepted the offer. As I eagerly sucked on her nipple, she leaned forward and reached back, grabbing my cock and inserted it into her ass. I sat up and continued to suck on her nipples as she rocked up and down on my cock. I felt something wet and sticky on my stomach so I stopped licking her nipples and looked down. She had cum without my even touching her cock. I looked at her quizzically. "Yes my love, it is possible to get pleasure from giving as well as receiving. Have you ever had a wet dream before? It is very similar, and your cock in my ass is a dreamy feeling" she said as she continued to move up and down on my rod. She leaned forward and began to lick and lightly bite on my nipples and that pushed me over the edge. I shot another load deep inside of her and moaned my appreciation. "Teri, you really seem to enjoy it when I have my cock deep inside of you, even to the point of having an orgasm, and that is amazing. Does that happen every time, does it feel as good to you as it does to me? Did it hurt the first time?" I was full of questions and she was happy to oblige me with answers. "Yes my love, I do enjoy it very much when my ass is full of your cock. Your cock is just the right length so that you rub against my prostate with each thrust. No I don't orgasm every time, but most of the time I do in fact get off on it, and it does feel wonderful. I started experimenting with vibrators when I was younger and the first time it was awkward, but I soon learned to love the feeling of being penetrated, lots of people do, not just women either." She said with a smile. "You say even men like it too? Well I guess that makes sense, we are the only ones with prostate glands and it is pretty apparent to me that you enjoy it." I stated evenly. She reached over and began to play with my nipple and said "I would be happy to show you how good it can feel if that is what you would like, but it has to be your decision. I don't want you to be on sensory overload, since this is your first time being with a special girl like me." I looked deeply into her eyes and took a giant leap towards the unknown. "Teri I would love to have you inside of me, I have enjoyed everything that we have done so far, so why stop now? I can't think of anyone who I would rather share that special moment with and I trust you totally." She smiled and got off the bed, went into the spare bedroom and returned with a tube of lubricant. "We need to make sure that you are ?freshened up' back there so this will be an enjoyable experience for you. I will slowly work this lube into your butt and start with a finger and then work up to three fingers. After you are comfortable with three fingers, it will be time and you and I will both know when that happens." I rolled over on my side to give her access to my ass and she gently applied the lube, carefully massaging it in and playing with her finger around the opening of my ass. At the same time she had one hand playing with my nipple while she slowly inserted her finger into my ass. "Just try to relax and enjoy the sensations on both you nipples and ass, close your eyes and just float with the sensations" she purred into my ear. I have to admit, the feeling of having a finger inserted in my ass was strange, but it was starting to feel pretty damn good too. Gradually she was up to three fingers and I began to squirm, feeling a bit uncomfortable. She stopped the in and out motion and just left the fingers inserted, to let me get used to the feeling. Soon I started to move my hips back and forth so I was controlling the pressure and became adjusted to these new sensations. "I want to feel you in me now Teri, please be gentle, but I would like for you to fuck me now." She gently removed her fingers and applied some more lubricant to her cock, spooned in behind. "Try to relax and just enjoy the experience, I am just going to put my cock at the entrance and let you control the penetration" she said as she rubbed her cock on the crack of my ass. I could feel her spread my ass and also felt the head of her cock between the cheeks. "Okay baby, I am knocking on the door, time for you to open up and let me in" she purred in my ear. I began to push back against her and could feel the pressure of her cock head against my hole. The initial feeling was of pain as I tried to accommodate the welcome intruder. "Take some deep breaths, relax and keep on going" she encouraged me while she played with my own softening cock. I could feel her licking at my ear lobe and I wanted this to be special for her as well for me. Gradually, the head of her cock passed through what must have been my sphincter muscle and I could feel her sliding inside me until her pubic hair and balls were against my ass. "Jack, I am all of the way in! My god, you are so tight and hot. I will just let you control the motion, how does it feel to you?" Now that the initial pain had passed, a wave of pleasure was washing over me. I could only moan in response and started to move myself back and forth against her. She must have understood because she continued to lick my ear and to play with my now hardening cock. I increased the tempo and began to feel a tingling throughout my body. I turned my head and kissed Teri deeply, my body visibly shaking with arousal. I could feel my orgasm getting closer and urged Teri "Please fuck me harder, I am ready to cum." Since I gave her the green light, she began to plow my ass with a vengeance, working on her own as well as my pleasure. I felt her stiffen and with one final thrust I could feel her sperm shooting into my ass. What a strange feeling, but it was really a defining moment for me. I loved it! "Now I know why you seemed to enjoy this so much when I was doing you, thank you for showing me how much fun it is both ways" I said as we continued to snuggle on the bed. I could feel Teri's cock softening and it came out with a wet plop sound. My ass was a little sore but I knew this was something that I would eventually get used to and learn to love. Teri jumped up and got some salve that she applied to my ass and told me it would soothe any lingering pain. Just having her massage my ass felt plenty good, and she also made sure to apply some internally too. "What a way to start the day, waking to a beautiful woman sucking my dick and then having that woman fuck me for the first time! I have so many new experiences over the past twelve hours that I feel like I have been missing out on a lot all of my life" I said. "Jack, you have just started to live, there is more to show and share with you if you are so inclined. Too bad we did not experience this back when we were in our teens, can you even imagine what we would be up to now! Heck, I might have even been able to get you to like dressing up as a woman, then I would not have had to been alone and fantasizing about you all of these years. Wouldn't that have been a kick?" she asked. "Fantasizing all these years? You make it sound like you have been in love with me since we were teenagers, is that really true?" I was looking at her with a confused expression on my face and added "And what is this about dressing up in women's clothing?" Talk about too much information, I was on overload and extremely confused. "Please tell me what you are talking about, but first, I think we should take a shower and you can experience the same thing I did yesterday" I said with a smile. Teri jumped up, grabbed my hand and pulled me towards the shower. End of Part 1, Should I continue or just end here? Please send comments to [email protected], I look forward to hearing from everyone, both good and bad.