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Chapter 1 As far back as I can remember my family was poor. My father died in a knife fight when I was only two years old. I don't remember him at all and except for a few pictures we had I couldn't even tell you what he looked like. My mother tells me he was a man of short statue and slight of build. He had blond hair that had enough of a reddish tint to it he acquired the nick name of Little Red. He also had very pale skin and eyes so blue they seemed to look right through to your soul. She also told me that I was his spitting image. Fortunately for me I had my mother instead of my father's mother. My grandmother encouraged my father to drop out of school and take a job in the trucking industry. My mother would have none of that. After my father had died my mother had to take a job as a housekeeper at local hospital. She worked hard to put food on the table and a roof over our heads. She was lucky to graduate from high school but even then she had no marketable skills. She wanted more for her son and she knew a good education was the only way to get it. She pushed me hard through school and was always checking my work. I could tell how disappointed she was with me whenever I brought home a grade that was less than an "A". Believe me I never tried too disappoint her. All through grammar school I got straight A's and I had perfect attendance. When I reached the eighth grade my principal called my mother in and told her of a prep-school that was offering scholarships to their school for deserving students from poorer families. Seeing my mother was a single parent I would be eligible. As soon as my mother heard about this she went right to work getting me a scholarship. She knew getting scholarships was the only way I would ever see the inside of a university. She wrote letters and filled out forms for two months before she got word back I had been accepted for the following fall semester. We were even given a grant to purchase uniforms. The following September after getting up very early and putting on my first school uniform I rode the two busses that would take me to my new school. When I arrived I was surprised by the size of the school. It was in a richer part of the city so it looked like it belonged there. Also the only kids that seem to attend the school came from the wealthier families. I quickly felt out of place and even though I was dressed the same as everyone else I was sure they could tell I didn't belong. Chapter two For the first month or so I was pretty much a loner. That was until I met Billy. He was quite a bit taller than I was and quite a bit bigger. He stood three inches taller than me and weighed at least thirty pounds more than I did, but none of that was fat. I would learn later that very few picked a fight with Billy and those that did soon learned they made a terrible mistake. The first time Billy ever spoke to me was in the cafeteria. I was looking for an empty table to sit at when Billy spoke up and said. "Hey Timmy come sit with me." I wasn't sure he was even talking to me then I saw him wave me over to the seat next to his. Billy and I became friends that day. I was never sure if he knew about the difference between our upbringing, but if he did he never let on. He treated me like he did any other boy in school. About two weeks after we first started talking Billy invited me over to house one Friday for a sleep over. I was ecstatic, as this was the first time I was invited over to any one's house. That Friday I went to school with a second backpack filled with two changes of clothes and a pair of pajamas. Billy's mom picked us up after school then went to another school to pick up Billy's slightly younger sister Janice. When we got to Billy's house I knew right off Billy's parents had quite a bit of money. Their home was huge, as it had six bedrooms. There was a study for Billy's dad and a sewing room for Billy's mom. Billy told me his mother never sewed a thing but that was what they called it. They had a big dinning room and a really big kitchen. Their basement was converted into a rec-room that had a pool table and an entertainment system. The rec room also had several couches, one of which pulled out to make a bed. I could tell instantly Billy's parents had lots of money, but as far as I could tell they didn't treat me any different than they would have treated any of Billy's other friends. I ate dinner with them and when I asked if I could help with the dishes Billy's mom laughed and said I was the first to ever ask that question. After she assured me she didn't need the help Billy and I went to the rec room to play. We played video games for several hours and then we played pool. Actually we chased the balls around the table for an hour or so as neither of us could make a shot. At eleven Billy's mom told us we had to get ready for bed and we had to lie down on the pullout but we could watch TV until we fell asleep. It had to be two or three in the morning before we finally went to sleep. Not once did Billy's parents come down to look in on us. The next morning Billy's dad drove me to the bus stop for my ride home. Over the next three months Billy asked me to spend the night every week. At first my mother wasn't too thrill with this but she did give in to every other week. It wasn't until December that anything changed. Chapter Three Two weeks before Christmas break Billy and I where lying on the pull out after his mom told us to go to sleep. After we both had heard his parents go to bed and the house became quiet Billy got up and went into a small room that held the heating unit. When he came back I saw he was carrying a magazine Billy flopped down on to the bed and said. "You'll never guess what I found in the garage." Billy then showed me the magazine. I knew instantly what it was though I never actually saw one before. It was an old copy of Playboy. "Where did you get this?" I asked. "I found a box of them in the garage. I think they belong to my dad but of course I never actually asked him if they were." Billy told me with a laugh. It wasn't long before we were lying side by side as Billy flipped through the pages. I for one had never seen a girl naked before. I had heard of the magazine before but never knew any one that actually bought a copy. I knew for sure, my mother never had. From the second I saw my first naked picture my little dick became hard. I was lying on my stomach and my dick was pressing into the mattress. Billy was lying much the same way I was but as we looked at each picture I could see his butt start to move back and forth. It wasn't long before his movements started to go faster and I could hear small moans coming from his lips. When I looked at his eyes I saw they were closed as he continued to hump the bed. A few minutes later I saw him shake as a long moan escaped his lips then he lay silent for a few minutes. After a minute or two he looked up at me and said. "Man that felt good." I was kind of dumbfounded at this point. I really had no idea what Billy had done and why it would feel good. Finally I had to ask, "What did you do?" "I jerked off using the bed silly." He told me with a laugh. I must have looked at him with a blank expression on my face. I really had no idea what he was talking about. Billy saw my look and asked. "Haven't you ever jerked off before?" "I don't think so." I told him. "If you ever did it you would know, it feels great." He told me. "Well tell me what to do. If it feels that good I want to do it too." I told him though I'm sure I sounded like I was whining. Billy laughed and said. "Role over on to your side facing me." I quickly did as I was told. I watched Billy's hand move down till they were at the snap to my pajama bottoms. With a flick of his finger he popped open the snap and pushed my pajamas out of the way. He next pulled down my underpants till my little cock was exposed. I was quite embarrassed by this, as I had never let anyone see my cock before. Well except for the shower after gym class and even then I wasn't hard like I was now. Billy next took my dick between his thumb and fore finger and started moving them back and forth on my dick. Instantly I knew what he meant when he told me about how great it felt. My eyes closed by themselves as he continued to stroke me. I moaned as quietly as I could though at the time I didn't know it. The feeling that was going though my body was unlike anything I ever felt before. I never knew anything could feel this good. I would like to say that I lasted a long time but I'm sure you know that can not be the case. It was too new to me and I had been hard for some time by this point. It seemed like he had just gotten started, when all of a sudden it felt like I had to pee. I felt a slight pressure around my pubic area and a second later it felt like my whole body wanted to cramp up as a warm and wonderful feeling flowed over me. A second or two later I felt my cock jump as I came for the first time. I couldn't believe how great that felt and I knew it wouldn't be the last time I felt that feeling. When my first orgasm had subsided I opened my eye once more and saw Billy smiling at me. With a cockeyed grin he said. "Pretty dam good isn't it?" "It was dam good. How long have you know about this." I asked. "Since last summer. I figured you already knew about it." He told me. "I never knew anything could feel this good. When can we do it again?" I asked as I reached down and started to stroke myself. Billy laughed and said. "I'm not sure but I do it a lot. Let's look at some more pictures and see what happens. Next time you can do to me what I did for you." The next time wasn't long in coming. Less than a half hour later Billy turned on his side and I saw his cock was already out. He then took my hand and guided it toward his cock. I knew what he wanted me to do without him even asking. I guess I should have been more tentative at the time but I really wasn't. I knew Billy was my friend and seeing he had done me I surely could jerk him off. I was quite surprised by the feel of his cock in my hand. First off his cock was bigger than mine was by quite a bit. It looked and felt twice as big as mine but I really couldn't tell you as neither of us ever measured our cocks at the time. His cock felt hard as iron but it also felt soft like a steel rod covered in velvet. It didn't feel real at first as it felt rubbery. But it did feel alive and quite warm. It also throbbed when I wrapped my fingers around it. Seeing Billy's cock was bigger then mine I was able to wrap several fingers around his cock as I stroked him. After a few minutes of stroking it felt quite nice and as the precum started to ooze out of his pee hole I used that as a lubricant. While I stroked his cock for him Billy laid his head on the bed with his eyes closed. I was surprised by the look of serenity on his face as I worked my hand up and down his cock. That look didn't last long as his orgasm quickly consumed him. It was a few seconds later when his eyes scrunched closed and a long moan slipped from his lips. I watched him shake slightly, as his cock seemed to grow in my hand. A moment later it looked like his cock exploded as a wad of white fluid gushed out of his cock and landed on my pajama top. I don't know why but I felt a feeling of accomplishment while I watched my best friend pump his cream. Once he had relaxed in the afterglow of his orgasm Billy looked up at me and said. "Definitely better when someone else's hand is doing the stroking. Look at the magazine for a few minutes and I'll do you again." True to his word Billy did just that and before we finally went to sleep we did each other again. Over the next three months we continued our jerk off sessions every few weeks. We also exhausted the adult magazines that Billy had found. Unfortunately the pictures we looked at left us with questions we couldn't answer. The pictures in the Playboy and Penthouse magazines we found didn't actually show what a pussy looked like. The girls always kept their legs together and with the hair that surrounded their pussies you couldn't see much more than their tits and ass. We also found the letters to be informative though again it left some doubt in our minds. That all changed the day Billy found a second box of adult magazines in the garage. Chapter Four It was in the beginning of March when Billy came up to me at school and said. "You've got to see what I found in the garage last Sunday." As excited as he was I was sure it was a new collection of adult magazines. When I asked him about it he said. "Man these are even better then the magazine we've been looking at. These show so much more." "So when am I going to get to see them?" I asked. "I asked my mom this morning and she said you're always welcome. Ask your mom tonight and see what she says." Billy told me as the bell rang for our next class. The following Friday I found myself once more as a quest at Billy's table. I could see Billy was excited about showing me the new magazines he found. While we waited for his parents to go to sleep we played video games but I could see Billy wasn't even thinking about what he was doing. While we lay on the pullout and watched TV we heard the unmistakable sound of the house settling down for the night. No sooner had we heard his parents climbing the stairs Billy went into the utility room and brought out several of the magazines he found. I saw instantly these were not the same magazines we had been looking at. The first picture was of a girl sitting with her knees opened wide. I could see her slit was open and her lips were spread invitingly. The next picture was a close up of her snatch and again I could see things I only had to imagine before. The pictures basically showed a couple having sex, though it was all done in still shots. A few of the pictures showed the girl with the guy's cock in her mouth and a few showed the guy licking her pussy. I even saw the guys cock in her pussy. The last picture was of the girl with sperm all over her face. Once we went through the first magazine Billy said in a whisper. "Didn't I tell you these were so much better than the other ones. Did you see how much of the guy's cock the girl swallowed." "Yea they are good and that girl must have swallowed half his cock to wrap her lips around the base like that." I told him in an equally soft whisper. "Roll over on to your back and I'll get you off first, then you can do me." Billy told me. This wasn't uncommon as Billy like stroking my cock first. So I rolled over onto my back as Billy pulled down my pajama pants and my underwear. As soon as my cock was free he took it in hand and started stroking me. I quickly closed my eyes and was soon enveloped in that wonderful feeling once more. I had learned to hold my orgasm at bay for a while and Billy was good at keeping me on the threshold for a while before letting me erupted into his hand. I was pretty sure this was be the case that evening until I felt something warm and wet on the head of my cock. When I looked down to see what was causing that feeling I saw Billy had changed positions. He was now on his belly next to me and his tongue was licking my cock. "What are you doing?" I asked as quietly as I could though it came out as a hoarse shriek. "I'm giving you a blow job." He told me as he looked up at me. "Why," I asked slightly confused at this new turn of events. Billy looked quite embarrassed as he said in a quite whisper. "I wanted to try it once just to see what it's like. If you don't want me to do it then I won't." It didn't take me long to come to an answer. If my best friend wanted to suck my cock I was willing to let him. "Okay," I told him. "But I'm not sure I can do you." Billy didn't answer as he lowered his mouth onto my cock once more. Billy didn't just suck my cock. He used his tongue as he swirled it all around my cock. This was something new for me and it was something that felt really good. It was a lot different than letting him jerk me off. Now I had a wet orifice to slide my cock into. The first time he sucked me off I didn't last very long at all. It felt too good and too wonderful and before I knew it I felt myself very close to orgasm. I told him I was going to cum and I tried to pull my cock out of his mouth but Billy wouldn't let me go. Once I realized he wanted me to cum in his mouth, I relaxed and let it happen. I let that warm wonderful feeling envelop me and a few seconds later I felt the first jet of sperm flash up my cock and into Billy's mouth. That first one was followed by several more, which Billy quickly swallowed. Once my orgasm had abated I looked to see where Billy was. He was lying on his side next to me with a smile on his face. Once he saw me looking at him he asked. "Well was that better than a hand job?" I just about laughed as I said. "Hell yes though I can't believe you actually did that." "I've been thinking about doing that for a while now. I was worried how you would react. I didn't want to lose you as a friend because of it." He told me shyly. Though I never thought about sucking cock before I said. "I guess I owe you a blow job in return." I didn't want him to feel bad about giving me one. "You don't have to if you don't want to." He told me, but I could see his excitement at the thought of it. "Let me try it and see if I like doing it." I told him as I started sliding down the bed. Billy protest once more telling me I didn't have to, but he quickly silenced his pleas once I took his cock in my hand. I started out stroking his cock like I had done so many times in the past. Though this time it was different. This time I looked over his cock like I never had before. His cock was bigger than mine is, though it wasn't a huge cock like we saw in the magazine. That cock looked impossibly large compared the one I held in my hand at the moment. And I thought to myself if that girl could suck his cock then I could suck Billy's. I felt a slight bit of nervousness as I leaned over and took Billy's cock into my mouth. Once the head was in my mouth I felt even stranger. I also felt a strong urge to gag. I quickly swallowed that down as I swirled my tongue around the head like he had done to me. As I slid my lips further down his cock it felt almost like it wasn't real. His cock was warm and tasted a bit salty but for some reason it didn't feel real. I wasn't sure how it should feel, as this was my first time. As far as blowing my best friend I felt I could do it. It wasn't like I was completely revolted by having his cock in my mouth but truthfully I didn't crave it either. I just figured I would get thought it for my buddy. As I started to pump my lips up and down on his cock I realized where someone could get pleasure out of giving head. As soon as I started to suck his cock and my lips started to rise and fall I heard Billy moan and I felt his cock flex in my mouth. I knew he was enjoying what I was doing and that gave me a slight thrill knowing I was giving him this pleasure. With that knowledge I pressed my lips harder on his cock and moved my head faster. By the time he was ready to fill my mouth with sperm I was really enjoying what I was doing. I knew how much he was enjoying what my mouth was doing and that made me want to continue. It was almost a disappointment when I felt him flood my mouth with sperm. He had warned me he was going to cum but I felt it was only right I let him fill my mouth like I filled his. Actually even though I knew he was going to cum I was still startled when the first load hit the back of my mouth with such force. That load dribbled passed my lips but I quickly sealed my lips around his shaft as the next five squirts filled my mouth. It was only out of necessity that I finally swallowed his load. It was either do that or drowned in it. Once he was done cuming I pulled off his cock and crawled back up the bed till I my head was on the pillow. He smiled at me and said. "That was great buddy. I hope we can do it again next time you spent the night?" "Why not Bill? I enjoyed it too, both giving and receiving." I told him. His next move surprised me even more. He slid his hand around my waist and pulled me closer to him. As his hand cupped my ass cheek his lips came down on mine. His kiss actually startled me so much I didn't pull back as I should have. I was frozen in place. After he had kissed me he grabbed the magazine and put it back in his hiding place. He then came back to bed and said it was time we went to sleep. I really had no idea what time it was and to top that off I was very confused. The next day after I had breakfast with his family his father gave me a ride to the bus stop. As I sat on the bus I thought about the night before. Actually I thought about the sex we had the night before and the kiss that Billy gave me. All through out the year it had been Billy that initiated every sexual encounter that we had. He also initiated every change that took place. I was starting to think he was gay and I wondered what that made me. But to be totally honest I went along with everything he suggested. And I couldn't deny that everything felt great. But I was sure I wasn't gay at all. After all didn't those naked pictures we were looking turn me on? If it wasn't for those I doubt any of this would have started. Maybe but who's to say. I came to the realization that even if Billy was gay it had no bearing on my friendship with him. But then again maybe he just wanted to have sex and having it with me was a way of getting it. I couldn't complain about it, as I enjoyed the sex we were having too. By the time I got home I realized that as far as the friendship between Billy and I there was really nothing to worry about. We were a couple of boys having some fun together. Later when the girls are more willing we would have fun with them too. From March till the end of May I would sleep over Billy's house two or three times a month. The oral sex we had continued during each visit and I would have to say I became quite good at giving Billy blow jobs. What was more surprising was we never got caught at it. The week before the end of school things changed once more. Though this time the change was devastating. I also experienced something I thought I would never experience again. Chapter Five As soon as we arrived at Billy's house Janice grabbed her overnight case and after kissing her mom goodbye she was out the door. I figured she was sleeping over a friend's house like she had often done in the past. Once Janice was gone Billy's mother turn to Billy and I and said, "Boys tonight Billy's dad and I are going out to dinner. After that we're going to a show then we're having drinks with some friends. I think you're both old enough to leave here by yourselves. Can I trust you two to be on your best behavior?" Of course we both said she could. I for one would never do anything to displease Billy's parents. I knew if I did I would never be invited back and that was something I didn't want. His mom thought for a second and said. "I'm serious boy. There will be no prank phone calls and no calling up friends to come over. You both know the rules about the liquor cabinet." Once we assured her we would be good while they were gone she went up the stairs to shower and change. When Billy's dad came home he also went up to change to go out. They ordered a pizza for Billy and I to eat for dinner. His parents weren't gone five minutes when Billy said. "Let's go take a shower." This was not uncommon as we always showered before changing into our pajamas later in the evening. That was also when Billy would bring out one of the magazines and we would lie next to each other on the pullout. Normally we would shower separately in the bathroom down in the basement. This time we went up to the bathroom that separated Billy's room from Janice's room. After I got undressed I step into the shower. I then received a surprise as Billy came in right behind me. "What are you doing?" I asked as Billy picked up a washcloth and started washing himself. "I figured why waist the time seeing there's no one else here." He told me with a chuckle. I thought this was kind of odd but I didn't say anything. We never showered together before and even at school we had separate gym classes. I also didn't figure there was anything wrong with it as we were only two guys taking a shower. That thinking changed when I felt Billy start to wash my back. At first I didn't know what to think. I never had anyone in the shower with me before. But I couldn't deny his hands felt good as they moved the washcloth around my back. It also felt good when his hands slid down and washed my bottom. By the time he started kissing the nape of my neck I was too aroused to stop him. Billy made sure I was thoroughly clean from head to toe. He even made sure my bottom was clean as he used the washcloth on my asshole for several seconds. I thought this was rather odd but it felt too good to make him stop. I really thought he would get me off in the shower. I was so close to orgasm that I was shaking like a leaf. Instead he turned it off and stepped out. I shook my head several times to clear it though that did nothing for my aroused state. I could have jerked off right then but Billy threw a towel at me and told me to hurry up. I really wasn't sure what was going on or what Billy was up to. I just followed his lead and dried myself off. When we walked back into the bedroom to get dressed Billy went to his dresser and said. "Seeing we're alone tonight I would like you to wear something different." He pulled out something red and handed it to me. When I looked at it I saw it was a pair of red lace panties and a red satin night gown. "I think these belong to your mother Billy. I don't want to get in trouble." I told him. "You won't." He told me. "You can change before we go to sleep and she'll never know." Billy held the panties for me to step into as I asked. "Why do you want me to wear them?" "I want tonight to be special. I want to play boyfriend and girlfriend." He told me. "Why do I have to be the girlfriend," I asked. "Because I can't fit into my mother's clothes and you can. Besides you're smaller than I am so it's only natural that you should be the girl." He told me as he pulled the panties up my legs. Once he had the panties settled on my hips he ran his hand over my lace covered cock. I could swear I saw him shiver as he ran his hand over the lace. I could also see his cock was rock hard and there was a long sliver of precum that hung from the tip. After he made sure the panties were just right he took the nightgown from me and slid it over my head. The night gown looked more like a short dress. It had thin shoulder straps that held it up and the skirt was really short and it flared out at the hem. I was actually surprised that it fit seeing I always considered his mother to have a slim figure. Once I was dressed and Billy ran his hands all over me he returned to his dresser to get dressed. He put on a pair of briefs and a pair of gym shorts followed by a tee shirt. He then scooped up a pair of pajamas and my back pack before taking my hand and leading me down to the rec-room. At this point I really didn't know what to expect. Normally we would play video games or shoot some pool until his mom told us it was time to get ready for bed. This time his parents weren't there and obviously Billy was going to move things along earlier than normal. Once we got down in the rec-room he pulled me over to the sofa and pulled me down next to him. I had thought he would go get one of his magazines but that wasn't the case either. Instead he wrapped his arms around my waist and started kissing me. We had kissed in the past. Normally it was after one of us got the other off. But we never kissed before hand. This time Billy kissed me hard and he slid his tongue into my mouth. As he kissed me I felt his hand move around me as if he was feeling me up. His one hand stayed on my back as if he was holding me while the other hand moved to my chest so he could play with my little nipples. I never knew that having my nipples squeezed and pinched would feel so good and before I knew it I was moaning into his mouth. Once I realized how good it felt I did the same to him. After he played with my nipples for a real long time his hand moved down and rubbed my cock through the satin night gown and the lace panties. Again how good his hand felt on me surprised me. He even reached behind me and rubbed his hand over my bottom. That too felt really good. I came to the conclusion that wearing his mother's clothes was turning us both on. The feel of the satin against my skin felt really nice and I was sure Billy thought so too. He seemed like he couldn't stop touching me. His hand was all over me as he continued to kiss me. I wasn't immune to this situation either. My hands moved over his body as well. I played with his nipples like he played with mine, but mostly my hand went down and I played with his erect cock through his shorts. I figured if he wanted me to play the girlfriend them I would do what I thought a girlfriend should do. It wasn't long before I had his cock out of his pants and I was stroking it as we kissed. When he finally stopped kissing me I pushed him back and bent over and took his cock in my mouth. "Oh yea baby suck your boyfriend's cock like a good girl." He told me as he pushed down on my head just a little. "I love it when you wrap your sweet lips around my manhood honey." Billy kept talking as I sucked him. He was never so vocal before but then again we were alone in the house. I guess he figured he could say what he wanted with out worry. I continued to suck him as he kept telling me how good my lips felt on him. He made sure to call me his girlfriend and refer to me in the female case. A few times when I had him close to orgasm he would call me a slut or his bitch but it was never said in a mean or derogatory way. Once he filled my mouth with a copious amount of sperm he pulled me off his cock and pulled me up so I was lying on top of him. He kissed me once more as his hand massaged my butt cheeks. We kissed for quite some time before he pulled up the nightgown I was wearing and rolled me over onto my back. By this point I was so horny I would have let him do what ever he wanted as long as I felt his mouth on my cock in the end. I really though he would suck me off but he had other ideas. I was actually surprised when he started to lick and suck on my nipples. I was surprised that my nipples were so sensitive. I knew girl's nipples were suppose to be sensitive and they would enjoy what Billy was doing but I didn't think I should. But I had to admit I enjoyed his mouth on my nipples so much I was moaning as I held his head close to my breast. Once he had sucked my nipples to his content he moved down and started kissing and licking my tummy. This wasn't too thrilling for me but I knew where it should lead so I let him have his way. Once he had licked his way down he started licking my cock through the lace panties. This felt pretty good to me so I didn't push him to wrap his lips around my cock. Just when I was sure he would start sucking me He took my leg in his hand and forced me to turn over on to my belly. This was something we never did and I wasn't sure I like where this was going. From the letters we read in the adult magazines I was sure he was going to do something with my bottom and I'd have to admit it scared me. When he started kissing my bottom through the panties I asked. "Bill what are you doing." "I making love to my girlfriend." He told me as he pulled down the panties. "Right now I'm going to lick your sweet pussy." "Are you sure you want to do that?" I asked with a slight tremble to my voice. "You know I do baby. Now relax and enjoy it." He told me as his tongue slid between my ass cheeks. I really thought to tell him no, I didn't want that. Once I felt his warm wet tongue between my cheeks nothing but a moan came out of my mouth. God his tongue felt so good I couldn't think of anything to say at that moment. Bill licked my ass crack for a long time and god that felt wonderful. That was nothing compared to what I felt when his tongue touched my anus for the first time. I couldn't stop the squeal that came out of my mouth the second his tongue touched me. It was like nothing I ever felt before. I wasn't the only one that was enjoying what Billy was doing. I could hear him moan as tried to push is tongue into my little hole. He seemed quite aroused by what he was doing. When he finally pushed his tongue into me I felt him shiver like he just had an orgasm. I know I was real close to having one myself as I felt his tongue slid into me. Bill licked my asshole for quite some time, as he seemed to really enjoy it. I of course wasn't complaining, as it felt so good. I also thought I could have an orgasm from this though I couldn't quite get there. When his tongue grew tried I felt something new enter my asshole. I was pretty sure it was his finger as it felt thinner then his tongue but harder at the same time. He started sawing his finger in and out of me as he asked. "Does that feel good baby? Do you like me finger fucking your pussy?" "Yes it feels good Bill. Not as good as your tongue felt but it feels good." I told him honestly. "I'm not hurting you am I honey?" He asked. "NO it feels good." I told him. "I'm going to slid another finger in your sweet pussy. So relax and go with it." He told me. When he started to push the second finger into me there was a slight bit of pain. I cried out slightly as he pushed in but that pain quickly vanished. Soon he was fucking me with two fingers. When he added a third finger it hurt a little more but like the last it vanished. Billy continued to finger fuck me. Once in a while I felt him pull out his fingers then put them back. Each time he did so they slid in easier then the last time. I was sure he was using some sort of lube but I couldn't say for sure. All I know was his finger felt slick and they felt really good inside me. I should have realized what Billy was up to. We had read several letter about guys ass fucking their girlfriends and I should have know Billy was going to try to ass fuck me. It wasn't until I felt him kneel up between my spread legs that I had an inkling of what he was up too. When I felt him move I turned my head to see what he was doing. I felt him spread my legs a little wider with his thighs then I felt something ease between my cheeks. "Bill what are you doing now?" I asked even though I was pretty sure I all ready knew. As I felt the head of his cock touch my anus he said. "I'm going to make love to my girlfriend." "I'm not sure I want this Bill. I'm afraid it'll hurt too much." I told him to put him off. I actually tried to get up off the couch but Bill held me down with his hand on my back. "Don't worry about it sweetie I'm going to take care of my girl. I'm going to go real slow and be gentle. I know you're a virgin and I don't want to hurt you." "Maybe we should talk about this before you do it." I told him but it was too late. The next instant I felt the head of his cock push into me. I guess I must have tensed up, as there was a shearing pain that that seemed to surround my asshole. "Oh god Bill that hurts oh fuck it hurts so much. Take it out take it out please." I told him in a scream. Bill stopped all movement. I felt him rub my back as he said. "Relax baby, stop trying to fight it. We both know you'll love it once you relax." As I tried to pull away from him I said in a whine, "I don't think so Bill it hurts too much. I could never love this." He still held me fast and no matter how much I tried to wiggle I couldn't move. The pain I was feeling did subside though it took its time. It left in stages as if I was getting use to having my asshole spread open. Once the pain had subsided I went totally limp under him. "Feeling better honey?" Bill asked once he noticed I wasn't tensed up any longer. "Just do it." I told him in resignation. "It doesn't feel very good but I can't stop you." "Don't be like that." He told me as he pushed his cock in a few more inches. This time there was no pain but there was a very uncomfortable fullness. It actually felt like I had to go to the bathroom real bad. I moved my bottom around a little and a few seconds later it didn't feel as uncomfortable. Bill started fucking me with what he had in me. He didn't try to go any deeper for a while though he didn't take it out either. I could tell he was really enjoying fucking me, as he would groan each time he pushed his cock into me. And I hate to admit it but not only was it not hurting any longer but it started to feel good a little. I can't tell you how long any of this lasted, as part of it seemed to last forever. I do know after a few minutes of his fucking me I started to feel him going in deeper. And by the time his thighs started to slap into mine I really starting to like getting fucked. I even heard myself moan each time he bottom out in me. Bill heard it too and I felt him start to fuck me faster as he said. "You like it don't you bitch. You like my big fat cock in your sweet pussy don't you." I knew his language for what it was. He wasn't trying to be mean or brag about his size. He was just repeating the things we read in the letters from the magazines. I also knew what I should say though I can't say I really meant them. "Oh god yes stud you cock is so big and I love how it feels in my pussy. Fuck me baby fuck me harder." I told him. I really didn't mean what I said. It just sort of came out that way. Bill must have thought I meant it. He slapped my bottom then said. "Get up on your knees slut so I can fuck your pussy good and hard." He pulled out and helped me to my knees like he wanted. As he tried to put his cock back in me I worried it would hurt again like the last time. Thankfully it only hurt a little and once he was in the pain vanished instantly. Billy started fucking me again. This time he reached around me and started rubbing my cock through the lace panties. I think we were both surprised when we realized my cock was still erect. I'm not sure if it was the fact that we had change positions or the fact he was rubbing my cock through the panties. All I know is it started to feel really good and soon I was pushing my ass back to meet Billy's thrusts. We were both moaning and grunting and Billy kept telling me how sweet my pussy was. I kept telling him how good his cock felt and how I wanted him to fuck me harder. At first it was just the words from the letter but after a while they were my own words. I truly loved what he was doing to me. I was the first to orgasm as this would have been my first of the night. I groaned out as my cock filled the lace panties with sperm. Billy was close behind, he grunted each time he sprayed a load of hot thick sperm deep inside my ass. Bill fell on top of me once his orgasm had run its course. I in turn fell flat on to the couch with Billy still on top of me. We both panted for breath as Bill's cock slowly started to shrink inside me. Once my ass had expelled his limp cock Bill pulled me close and whispered. "Dam that was the best sex we ever had. I hope you enjoyed it as much as I did?" I turned my head so I could see his face before saying, "It really hurt at first but after I got use to it was pretty good. I wouldn't mind doing it again, just not tonight." Billy kissed me before saying. "I don't think we have the time. It's all ready midnight and I'm not sure what time my parents will be getting home." Bill patted my bottom and said. "Come on girlfriend we need to clean up before they come home." Even though I didn't want to move I followed Billy in to the downstairs bathroom. As I walk to the bathroom I could feel his sperm leak out of me. Bill stood in front of the sink and washed his cock off while I stripped out of the panties and nightgown. I then sat on the commode and tried to push out the rest of his load. I found out later that night, I wasn't too successful. I leaked sperm the rest of the night. As I cleaned the lubricant off my bottom Bill took the panties to the laundry room and washed them out. He then threw them into the dryer for ten minutes before placing the panties and the night gown into the dirty laundry. He didn't want his mother finding the panties with cum stains. Once we were dressed in our pajamas we lay down on the pull out and turned on the TV. We just started to watch a movie when we heard Billy's parent come home. Billy's mom came down the stair and looked around for a moment before saying. "I knew I could trust you two. Thanks boys for being good." She gave us both a kiss on the forehead before going back up the stairs. I'm not sure if she heard, but we both started to laugh. If she had come home a half hour earlier she would have caught us having sex. Chapter Six The last week of school was exciting and boring. Monday and Tuesday we had finals. On Wednesday and Thursday we didn't have to go to school if we didn't want to. Though we would be marked absent if we didn't show up. I was still working on my perfect attendance so I went to school. Billy was there the first two days but he missed the second two. Every time we saw each other he told me about how he fucked his girlfriend as if I wasn't there. He was real careful not to let anyone else hear but even if someone had they wouldn't have known it was me he was talking about. Even so I couldn't help blushing each time he said his girlfriend had a sweet pussy. On Friday when I saw Billy that morning I knew there was something wrong. He looked like he could cry at any moment or he had on the way to school. When I asked him what was wrong he said. "We have to move. My dad took a new job in California and we have to move out there by next month. This really sucks." I couldn't believe what I was hearing. My best friend was moving away. I was devastated. Not only was he my best friend but he was my only friend. I knew his parents had planned a three week vacation to Florida after school was out. "Are you still going on vacation? When did your parent tell you about this?" I asked. "After finals. They didn't want us to know about it before we took our finals. We leave tomorrow morning for Florida then we go straight to California from there. I'm never going to see you again." He told me. He actually looked like he was going to start crying. I felt sorry for myself because I was losing the only friend I had. I felt even sorrier for Billy he was losing everything. The home he had known his whole life, his friends and his school. Sure there will be others but it will be hard on him for a while. Billy fought back his tears and said as the bell rang for our first class. "My mom want's you to come over after school so she can say goodbye." I wasn't sure I wanted to do that but I knew I didn't have a choice. It would be rude not to go. Getting straight A's for the year and making honor role for four semesters didn't seem like such a big deal any longer. I knew my mother would be happy for me but it didn't make up for losing my best friend. Thankfully we had shorten periods so we could get out by noon. It actually was a mixed blessing. I didn't have to stay in school all day but I also didn't want the day to end. When it did I would lose my best friend forever. Billy and I walked to his house after school. Neither of us said anything the entire way. We both felt awful about this change in our lives. When we walked up to his house I saw a larger blue moving truck in his driveway. I could see the movers were already moving out furniture. We walked into the house and saw his mother had made lunch for us. As soon as she saw me she started to cry as she hugged me. I had tears in my eyes too. Once she got herself under control she said. "I feel like I'm say good bye to one of my own children. I'm sorry we have to leave but this new position Billy's dad is taking is too good to pass up. If I could I would take you with me but I'm sure your mother would be quite angry with me if I did." My mother would have been angry but I also knew I could never leave her. I was all she had. After we had lunch Billy's dad drove me to the bus stop. It wasn't like they didn't want me around, they were busy with the move. I was kind of glad as well seeing it was too sad to watch the movers taking out their belongings. The bus ride back to my apartment was one of the saddest rides I ever took. I could feel myself coming closer and closer to tears through out the ride. I didn't actually cry thought I was very close by the time I got home. When I got home I was all alone. I knew this would be the case as my mother worked till eight at night and some times later. Seeing I didn't have much to do that day I started emptying my school backpack for the last time that school year. When I open my pack I found a large yellow envelope that I knew I didn't pack. On the envelope I saw Billy had written a note saying, "I didn't want my parent to see me giving you this. It would be too hard explaining what was inside. Remember you will always be my best friend and my secret girl friend. Enjoy yourself and tell my girlfriend I'll miss her sweet pussy." When I looked inside the envelope I found the red satin night gown and the red lace panties I had wore the week before. I also found three of the hard core magazines. Two of them I had seen several times in the past but the third one I never saw before. As soon as I started looking through the magazine I instantly knew where Billy got the idea of dressing me up and fucking me. The third magazine had pictures of guys that looked just like girls except they had a cock instead of a pussy. Over the next year or so I often slipped off my clothes and dressed in the nightgown and panties while I looked through the magazines and stroked myself though the panties. I don't think my mother ever found them seeing she never said anything about them. I'm not sure how she would have handled it if she knew what I was doing.