Meeting Jenn: How I Fell In Love With My Best Friend. Chapters 1 free porn video

MEETING JENN CHAPTER ONE; It Started With a Text **I need 2 talk 2 u.** was the first text I got that night from Jimmy. It was a Thursday night and I didn't expect anything unusual was going on. I thought about Jimmy for a second, he's been my best friend since we were both in second grade. I knew though that if it was an emergency, he would just pick up the phone and call. I punched quick text back to him, **K, what's up? U want me 2 call u or u wanna call me?** I threw down the phone and headed for the kitchen. I had just gotten home from work and hadn't even had a chance to jump in the shower yet, I had only been able to throw on a pair of basketball shorts by this time. I reach in the fridge and grab a beer. I can hear the chirp of my cell phone from the living room letting me know that I just received a text so I grab my chew can and spitter off of the counter and head that way. I plop down on the couch and grab the remote. There's no urgency in my actions, after hearing that I got a text, I assume that either Jimmy wants me to call him or he just wants to chat via text. I crack open my beer and take a swig. "Let's see who's playing in the Thursday night football game." I say out loud to myself. I hit the remote three times and I have the channel on. I see right away that tonight's matchup is between the Pittsburgh Steelers and the Baltimore Ravens. Blahhhh... I have no real interest in this game as I don't care for either team. If the Raiders were playing the Chiefs, Jimmy would be sitting right next to me. Him cheering on his Chiefs while I yell and scream for my Raiders. I grab my chew can and pull out a big pinch of the stinky tobacco. After I stuff that in my lip I toss the can to the side, tuck my spitter between my legs, grab my beer and just sink back in to the couch. 'Okay Jimmy, what's going on with you?' I think to myself. There's a text from him and I open it. **Michelle's gone tonight and I decided to play around some.** was all it said. Michelle is Jimmy's girlfriend, they live together and have been going out for the last three years, since they were both 21 years old. She's okay I guess but I really can't stand her. I had no clue what the hell his text meant. 'Was he gonna cheat on her? Did he have some girl over there right now? Oh shit! Do I know this girl?' These were just some of the thoughts that were going through my mind. I quickly enter a text and press send. **Um... not sure what u mean???** I spit a mouthful of spit into the Dr. Pepper bottle that was between my legs. It's a disgusting habit and I wonder if I'll ever find a girl that can accept it. My phone dings again, Jimmy is responding quickly. The game's still on in the background but I can't pay attention to it due to Jimmy and his texts. I grab the phone hoping that he'll just get to the point. **I know I can trust u. Ur the only one I can talk 2 about this.** was his response. Now I worried, Jimmy has something going on and he needs to talk to someone. I'd be there for anything for this guy so I naturally send back an encouraging text. **U know u can tell me anything. What is it man? U got me worried.** I feel like calling but know if he wanted to "talk" about this he would've called. **I'm gonna send u some pictures. I'll explain as we go along.** was the next text followed immediately by **Plz don't show these 2 anybody. I kno u won't. I don't wanna lose u as a friend Will so if I go 2 far let me kno and I'll stop.** followed by a third text in a row. **There's about 10 pictures total. Like I said, I'll explain as we go and don't hesitate 2 tell me 2 stop.** After these three texts I was both intrigued and worried at the same time. Jimmy sounds like he's got a crisis on his hands and I wanna be there for the guy. So far, I think I can piece together that he's got pictures of something and he needs to show me them to explain it. Also, He mentioned that he didn't want to lose me as a friend so whatever he did, it's serious. I get the feeling that Jimmy's gonna try and gross me out or something so I prepare myself for whatever's about to be sent to me. I wait for the pictures for what seemed like an eternity but was probably only a minute or two. There's two dings in a row so I know I got multiple texts. The first is a picture. 'Screw the text', I think to myself, I wanna see what the hell is going on. I open the picture and am at first puzzled by what I'm looking at. It's a picture of Jimmy, I'm sure of that. He has his hair in a low ponytail, this isn't out of the ordinary, Jimmys had longer hair now for about 2 years. He's always said that Michelle likes it long. It's not excessively long, it stops just below his shoulders. I've seen Jimmy with this style of ponytail many times in the past. It's not the hair that concerns me... It's the makeup Jimmy's wearing. I look close but can't really see enough. I save the picture to my phone, close down the text and go in to my galleries. It's the first picture and I open it. The picture is much bigger this way and a lot easier to see. There's no doubt that Jimmy's wearing makeup. It looks like he has a light coat of foundation on. I guess this only because his cheeks look like they are a lighter shade than normal. The only other makeup he has on is on his eyes, but they are made up well. He has a thick, black line of eyeliner tracing each upper lid. Below each eye there is also a thick black line of liner only this one stops three quarters of the way towards the inner eye. He has the very top of the bottom lid lined the same way only this looks like it was done by an eye liner pencil. I can tell he also has mascara on and a medium coat of a brown colored eye shadow. Nothing else, no lipstick or rouge, just the eyes and some color on his cheeks. I wonder to myself 'why he's doing this?' or 'what's going on?' but assume that's what the second text is all about. I close the picture down and go back to my messenger. **I started playing with Michelle's makeup. This is what I came up with.** That's all he had to say. 'That didn't explain anything' I thought. My phone dings another three times. Three more texts but first I still wonder to myself, 'why is he wearing makeup?'. With three more texts waiting I break my line of thought. There are 2 text messages and a picture message waiting to be opened. I want more of an explanation so I open the first of two texts. It seemed strange but this is what it read, **I didn't kno what 2 do next so I wondered, what would Will like?** It was short but not nearly enough. The next one read, **I figured I HAD to do something with my hair**. I braced myself, I knew the next picture was gonna be Jimmy with his hair done up. Before I could open the picture text my phone dinged once more. I could see that the next text was a single text message, not a picture. I kept going through the texts in order and opened the picture message next. Not knowing what to expect it wasn't as bad as I thought it could be. Jimmy stayed away from the dramatic and instead his hair was just kind of... fluffed out. I could tell that he had used a curling iron but for the most part his hair just looked fuller and semi styled. Looking at the picture, he was actually kinda cute, If I just ignored the fact that the cute, little, pudgy girl I was looking at was actually my best friend since childhood. I call him pudgy but he really isn't, I should describe what Jimmy looks like. Jimmy's always been small. I was blessed in this department standing six foot two. Not Jimmy though, he only measures up to five foot five. He's been a runt since the day I can remember. There's been a joke floating around since Jimmy started dating Michelle but I won't repeat it now. They're the same height so it's a pretty easy situation to make fun of. I'm tall and skinny, I weigh 200 pounds but with my height I still look too thin. Jimmy weighs in, I'd say, right around 135 pounds. Like I said, he's not pudgy. The reason for the pudgy comment comes from his little, rabbit front teeth. His mouth resembles Selena Gomez's, they both have similar "chipmunk" cheeks and when he smiles he has that same Bugs Bunny grin that makes Selena look so cute. As I mentioned before he has hair that ends just past his shoulders. It's thick and a light shade of brown, and to be honest, I had never really paid attention to his hair other than the length. He has hazel eyes that sometimes look to be a gold shade of brown and at other times can look to be a shade of green. His features are delicate for a guy but that's all because of his cheeks and the shape of his mouth. This, I now notice, gives him a more feminine look. Other than that he's pretty non- descript, a small, thin kid. I move on to the final text and once again am left wondering where this is all going. **After that, I wondered where 2 go next. I wondered 'What would turn Will on?' and then I dwelled on conversations from the past.** My phone dinged again, but I had to finish this text first. I read on **I remembered that you said you like ringlets.** I finished the text and moved on to the next as fast as I could. Again, it was another text message, It simply asked, **r u still there?**. I responded but first wondered how long I had been lost in these texts. I looked up at the TV and the first quarter was just coming to an end, I had been sitting here for only 20 minutes. I responded to Jimmy with **I'm still here.** It seemed as if he responded instantaneously and I read his response. **Should I keep going?**. I didn't know how to answer and typed the first thing that came to mind, **Sure**. Before I could even proofread it I had pressed send. I sat there hoping that I didn't come off to eager. I timed how long it would take for me to get the next text. It came out to one minute and forty eight seconds before I got 3 consecutive dings. All three texts were picture texts. I tried to gulp but my throat was dry, both from the chew and what I thought I was about to see. Before I opened the first picture I took my pointer finger from my right hand and scooped the chew from my bottom lip. I took a swig off of my beer and realized I must have been drinking it the whole time as it's empty after that last drink. I get up and shuffle my socked feet to the kitchen. I throw my empty into the trash as I pass it and go to the fridge. I grab 2 of the Bud Light tall boys and head back to my spot on the couch. I snatch my phone up like a giddy school girl waiting on a text from her new crush. I crack open my beer and take a large gulp while working the phone with my right hand. I open the first picture text. It's a picture showing Jimmy smiling at the camera only now he has a bump on the front of his head, a little poof of hair standing about an inch and a half tall. The fluff and fullness are now gone, it looks like he straightened his hair with a flat iron for this picture. I can tell he had spent some time doing all of this. 'Okay, that wasn't as bad as it could have been.' I thought to myself. I open the next text now and start to see where he's going with this next move. In the picture Jimmy has a curling iron held up to the left side of his face. I could see his hair wrapped around the barrel of the iron. It shined and looked silky and for a moment I wondered how Jimmy learned to curl his hair. With the third picture Jimmy started to peak my interest. It was just Jimmy staring at the camera, no real expression on his face but what caught my eye the most was the curl now dangling from his left side. It was perfect and I wanted to play with it. I was having "feelings" and it was Jimmy that was giving them to me. The curl shined and looked like the type of curl that if pulled would spring back to the exact curl that I'm looking at now. I shook my head and went for another gulp of beer. It had been six minutes since the last picture and I was growing impatient. I sent a quick text to Jimmy. **Where's the rest?**. I got a text back right away, **:)**. I knew that must have put him at ease. I wasn't telling the guy to go away and I wasn't calling him a freak. Within a minute I got two more texts, both the picture type. Before I could even get the first picture open I received two more picture texts. I now had 4 pictures waiting for me. I did the quick math and came up with 11 total pictures. This has to be all of them, he told me 10 in the beginning and we're at 11 now. The first picture now shows Jimmy holding the curling iron on the opposite side of his head, a curl wrapped around the barrel. There is one difference though and that's the left side. Now instead of the one dangling curl there are a bunch of them. The whole left side of his head is covered in nice rows of ringlet curls. I now remember the conversation I had had with Jimmy where I had admitted that ringlet curls did it for me. I told him there was only one other thing that turned me on as much and that was a cute girl that smokes. At some point, and I don't know when, my left had slipped down inside my basketball shorts. It was now rubbing my half hard penis. I noticed it but didn't stop. Jimmy's curls were starting to drive me crazy. The next two pictures were almost identical. The first showed only Jimmy's right eye and a curl wrapped around the barrel. The picture was taken only a few inches from his face but the look was perfect. I could see the individual strands of hair wrapped around the rod. His eye makeup was perfect and I focused on the gold/brown eye that stared back at me, surrounded by black eyeliner. The third picture was shot even closer and it was only his eye. Again, I wondered how he learned to apply makeup so well. The fourth and final picture was the finished product, Jimmy with his arms crossed, his made up face and sly little grin. His bump seemed to stick out even more now that it was surrounded by bunches of ringlet curls created with a 3/4" barrel from a curling iron. He looked cocky, like he knew he looked good and he did. My dick was now fully hard and I was slowly moving my hand up and down the full length of my shaft. I figured this was over and got ready to jack off to the thought of my dick wrapped with one of Jimmy's curls while other curls tickled the bottom of my scrotum when my phone dinged again. **It was still early and I thought what next? What would make Will cum?** I don't know why Jimmy is doing this but I don't want him to stop. Before I can text him, I get another text message. **I looked around the house and then it caught my eye. Michelle left a pack of her Marlboro Light 100's here.** My eyes shifted to the left as a thought raced through my head. 'He's not gonna', before I could finish the thought my phone dinged, I grinned. It was a picture message and just then I was grateful for best friends. It took me less than 15 seconds to get the text message open and in those seconds I received another. I opened the first picture and my wish was granted. There was a picture of Jimmy, a long, all white Marlboro Light 100 dangling from his pouty lips. I could barely see his bump but had no problem seeing the dangling curls surrounding his face. His eyes were focused on the end of the cigarette, he held a lit lighter to the tip. His cheeks were hollowed inward, the cherry burned bright, I could tell he was really inhaling. Jimmy wasn't a smoker. Jimmy chewed but he didn't smoke. In fact, he always complained about Michelle's smoking. Maybe it was the piggish way she did it, she looked like a slob when she smoked. Jimmy was concentrating on turning me on and it was working. My phone dinged twice more while I was looking at the first picture. I now had three waiting for me. Looking at the light in the background of the first picture, I could see that it was dusk when the picture was taken. It was dark now and I assumed that the picture was taken about an hour ago. I shake my head in a quick little motion and get back on task, on to picture number two. This one just shows Jimmy sitting in a chair, a grin on his face, holding a cigarette. The cigarette was held between his stiff pointer and middle fingers, his hand was cocked to about a 22 degree angle. His fingers looked long and dainty, the cigarette was still long and smoking. The third text showed Jimmy inhaling, the cigarette now half burned. Taken from the side it was meant to show me that he was really inhaling but instead I focused on the many curls, where his face started and his hollowed cheeks. I now played with only the head of my penis. I didn't want to cum yet, I knew there was at least one more picture. In fact there were several others, eight smoking pics in all. It would be the last three pictures that sent me over the edge. Still, to this day, I think of those snapshots. The first of the last three was simple, it was Jimmy taking a drag. He held the cigarette with his right hand to the right corner of his mouth. His head was slightly tilted back and I could see two well defined ringlets and his bump was silhouetted perfectly. His eyes were rolled back somewhat and pointed off to the right. His cheeks weren't hollowed but from the angle the picture was taken his chubby cheek looked like it wanted an inviting pet. I opened the next text and my dick started to twitch. I had to control myself, I didn't want to cum just yet. The second to last picture was the exhale. In it, Jimmy's in the same position, only now he's blowing smoke out of the same exact hole where he had just inhaled. Eyes rolled up and to the right, lips pointed in the same direction, a steady stream of white smoking exiting his mouth. Something about the picture, his eyes, his pointed lips, the smoke... I was on the edge. The last picture did it. Jimmy with his right hand curled under his chin, like the statue "The Thinker". His head slightly turned to the right, with the look of a distant gaze. Curls hung down to his wrist, his eyes seemed to sparkle, outlined and dark. His left hand held the cigarette, you could tell his left elbow rested on his thigh. HIs hand was curled in almost an "O" symbol, his thumb touching his pinky, the cigarette sticking straight up from his half curled index and middle finger. He looked sexy in what reminded me off a pose I would have seen performed by the likes of Marilyn Monroe. I couldn't hold it any longer and in one awkward motion reached for my spit bottle. Twisting the cap off in a feverish manner I rush the opening of the bottle to the tip of my penis. I've dropped the phone by now and proceed by memory, my right hand rubbing the underside of my dick. I think of what it would be like to have Jimmy next to me at that moment, him smoking while I cum. I explode into the bottle. My dick spasms close to 6 times, I hadn't cum in days and it feels like it. I moan while in the middle of climax, at one point moaning out the name "Jenny". My heart's still racing when my phone dings once again. It's a text from Jimmy... **What r u doing? Mind if I come over? I'm all dressed up with no place 2 go...** Still trying to recover from getting off I glance at the clock. It's only 8:30 and the night is still young. I respond trying to act cool, trying not to act like I just got off to pictures of my best friend with makeup on, his hair curled and him smoking cigarettes with the intention of getting me off. **I got nothin goin on. If you wanna come over I'm here. Gotta ask tho, r u comin over or Jenny?**. He respond right away, **Jenny... I like that. She wants to meet u** My head darted from side to side looking around the apartment to see if it was presentable enough for a girl to come over. I stopped and shook my head, 'what are you doing? It's Jimmy, he's seen this place a lot worse than this' I thought to myself. My attention turned back to my phone, I swiped a message and sent it off, **Yeah, come on over.**. Again, I received his text in seconds, **k, b there in 15 mins.**. I laid back into the couch and thought for a while. 'This shit is crazy. How did this happen? Jimmy's on his way over dressed as a girl. I've already jacked off to pictures off him and now he's headed over... for what? Where's this going? What will I do? I won't risk the friendship, Nothin's gonna happen, nothin's gonna happen. But what if it does?'. I broke my train of thought and snapped back to reality, I figured I should at least take a whore's bath and wash my pits. I should put some real close on instead of these junky shorts and t-shirt. With those thoughts I got up and made my way to my bedroom. I threw on a pair of jeans and clean socks, grabbed a nicer t-shirt and headed for the bathroom. After washing my stinky spots I throw my t-shirt back on, put some deodorant on and give my hair a brushing. I hear my phone ding and if Jimmy's here he made it pretty quick. I make my way back to living room and as I pass through the kitchen I can see a set of parking lights on the street. "SHIT! He's here.", I whispered out loud. I reach down and grab my phone. **I'm here.** CHAPTER 2; Meeting Jenn Just as I'm pressing the button to get me back to my home screen I hear a knock on the door. That's strange only because normally Jimmy would just walk right in. I throw my phone down and head for the door not knowing what to expect when I got there. I undo the deadbolt and slowly open the door and there was Jimmy, now dressed as a girl, staring up at me all doe eyed through a pair of studious looking women's eye glasses. In a soft feminine voice he said, "Can I come in?". I made a small motion with my head, moving it slightly backwards, kind of a 'I'm in shock' movement. I hadn't expected that voice to come out and now that it had I liked it. I stepped to the side and without saying a word I motioned my arm as if to say 'Right this way miss'. Jimmy smiled and slowly made his way past me. I looked him over as he passed, the typical male checking out a female pursatory look. 'He has boobs and a nice but' was the thought that came to mind. He got to the edge of the kitchen counter and set his purse down. I hadn't seen the purse till that moment and it kind of surprised me. It made me realize that this was real, this was happening. He turned and faced me, sticking his right hand out as if to shake hands. "Hi, I'm Jenny. Nice to meet you." he said still with that soft, sorta whispery, feminine voice. I reached my hand out and said, "Hi, I'm Will. Nice to meet you." I felt like a dork but didn't know what else to say. He motioned his right hand up and down in a Price is Right sort of way and said, "I'll give you a couple seconds to check me out and soak all this in" and smiled big. He was all teeth and cheeks and looked cute as hell. I looked him up and down starting at the top and working my way down. He still had the bump and the ringlets and it looked like he had freshened up his curls since the pictures were taken. Now, in person, the curls looked even better. Close to 30 medium ringlets, all stiff and bouncy, waiting to be played with. Each like a longer toilet paper roll, light brown hair that shimmered with blondish highlights. I had never noticed the highlights in Jimmy's hair before tonight, before his hair was curled. His bump showed highlights too, two little blonde streaks, one on each side. I wanted to squish it lightly and watch it bounce back up, I wanted to play with his hair. Jimmy had on a pair of medium sized, gold hoop earrings. I knew his ears were pierced but I had never seen him with anything more than studs in his ears. His makeup was the same, only now he had a light shade of shiny red on his lips. His outfit was simple and not overly feminine. He had on some kind of black halter top and I only call it this because of where it started and stopped. The top started about 4 inches above his hips, showing off plenty of belly. His tummy was tanned and hairless and I couldn't help but notice how tight and fit he was in that area. The top hugged him well as it worked its way up. He had a good amount of cleavage sticking out of the top and his shoulders were bare except for the inch wide, black strap on each side running over to the back. The top ended just under his armpits which had to be shaved to wear a top like that. I would say his boobs were about a "C" cup and I wondered how he had created the illusion. He was wearing black Capri pants that started around mid-hip so you could see the upper portion of his hip bones sticking above the pants. They were skin tight and stopped just below the knee where the bottom cuff had a slit on each side. His legs from knee to toe were tan and shapely and I noticed they were hairless too. He was wearing black, velvety looking, high heeled platforms. The whole process of looking him up and down only took seconds but it seemed like an eternity. Finally, he spoke again. "So... do I pass?". I just nodded my head without saying a word. I've always been the quite, shy one of the 2 and Jimmy's the outgoing extrovert type. I sense that he felt I was spinning, looking for the right words but not finding them. He started talking more or less to break the uncomfortable silence. "Mind if I make myself something to drink?" he asked. Without letting me answer he turned and walked over to one of my cabinets. I watched as he stretched to the top shelf, fiddled around and then brought down a wine glass. He set it on the counter and the pulled a bottle of white wine from my liquor cabinet. He poured himself a glass, then turned and asked, "Would you like a beer?" again, I could only nod my head. With that, he walked to the fridge, his heels clicking on the hardwood. He stopped and opened it, I still watched. He bent over at the waist to fetch the beer. Straight legged and bent at the waist, I stared in disbelief. All I could see was ass and legs, both very tight and trim. I was turned on to say the least and Jimmy must have sensed this. Still bent over, he looked back at me sort of around the side of his leg, and caught me checking him out. He started to say, "Bud or Bud Li..." his words trailed off. "William Norton... Were you just checking me out?" I didn't say a word but am sure I turned ten shades of red. He turned back to the fridge mumbling "He was checking me out." Jimmy was loving the attention. He walked over and handed me the beer, his wine glass in his right hand. "Shall we sit? I suppose you're wanting some answers." He said. I finally spoke, "Yeah, you wanna head to the living room? We can talk there." Before heading that way he asked, "I'm wondering if you'd mind if I smoke? If not, I'm gonna need an ashtray." I started walking to the cabinet where I kept that kind of stuff. "I don't mind. Let me grab you one." I reached up to the top shelf and for some reason looked back to ask him something. Jimmy was staring at me with that same mischievous look I must of had on my face when I was checking him out. "Were you just checking me out?" I asked in a playful voice. "Yes I was." was Jimmy's answer. I turned back and we both walked to the living room. I sat in the right corner of the couch facing the TV, with my beer resting between my legs. Before sitting down, Jimmy reached down and did something to both shoes. He kicked them off and climbed on to the couch next to me, now barefoot. He crossed his legs under himself, Indian style, and faced me. He leaned far over to his right and gently slid the coffee table towards us. He could now reach his wine glass and the ashtray that was on the table. He took a sip of his wine and set it back down on to the table. I couldn't help but notice the lipstick mark his lips left on the glass. He reached towards his crotch with both hands and before I knew it, he was holding small cigarette purse. I hadn't seen where that came from nor did I care. Still without saying anything he looked down and twisted the gold clasp and the purse was open. He flopped open the box top and pinched the tip of a cigarette and pulled. Time seemed to slow as he pulled the cigarette from the pack, the cigarette seemed to go on forever. A quick flip of his fingers and he was holding the smoke between them, the fingers were already stretched straight out. He brought his hand chest high. His left hand, holding a lighter, raised at the same time. He stopped mid motion, "Well... do I start with the smoking or the way I'm dressed?" he started giggling in a very girly way. I ate it up. He seemed very petite and cute. I reached my hand out "Here, let me light that for you." He didn't resist and handed the lighter over. I adjusted it in my hand as he brought the cigarette up to his lips and leaned towards me. I flicked the lighter and moved it to the tip, he started a deep drag as I pulled the lighter away and stared. He turned his head a little to the right, still inhaling, almost as if he was self-conscious because I was watching. In a quick motion he moved the cigarette from his mouth, cocked his head in the air and exhaled. It was the type of exhale accompanied by a whooshing sound as the air and smoke moved past his pouty lips. He rested the hand with the cigarette on his right knee and began to speak, "You can probably tell I've been smoking for a while now." He brought the cigarette back up to his mouth and took another long drag. Again he exhaled without looking at me, I could tell he was worried but he continued. "These aren't Michelle's cigarettes, they're mine." He kind of chuckled, "You can probably tell that this isn't the first time I put on makeup and did my hair. I've been doing it for a while now." I reached out and put my hand on his left hand, gently holding it. I wanted him to know that I was there for him. Staring at the beauty in front of me, my instincts started to react. I stroked his tiny hand with my thumb, rubbing back and forth. He went on, "You can probably tell that these aren't Michelle's clothes, they're mine." A tear trickled out from behind his glasses, I reached up and wiped it away. He finally made eye contact with me... "Where do I start Will?" he asked and then took another drag. I was gonna answer but before I could he exhaled and started talking. "There's been another side to me since as far back as I could remember. Funny enough, I named her Jennifer, the same name you referred to me as. I go by Jenn but prefer you call me Jenny. I dressed up every once in a while when we were in High school. I'd wear my mom's clothes and would play with makeup for the first time. Nothing serious though, I was always afraid of being caught by one or both of my parents. Once we graduated high school, I dressed more often still not knowing what I wanted out of all of this." He took a final drag from the cigarette and gently put it out in the ashtray, only half was smoked, he set it to the side as if he'd finish it later. He picked up his wine glass and finished the last drink. He went on, "Then I got together with Michelle. At this point Jenn hardly ever surfaced. I was afraid of being caught as I'm sure you could understand. The problem was, all of a sudden, I had a rather large collection of clothes and make up thanks to Michelle. I fit in to all of her stuff, but to be honest, it was all too big. Michelle's a little heavier than me and her clothes wouldn't fit... 'Just right'. The fear kept me from dressing up and I would only get to express myself 3 or 4 times a year. Not nearly enough to satisfy the urges I had for Jenn to come out. Then, what seemed like an act of god, Michelle was put on the night shift. I had hoped something like this would happen because I knew with her at work I would have plenty of time for Jenn to emerge." He stopped for an instant, "Can we pause for a second? I need more wine." Without letting me answer he was off towards the kitchen. He yelled, "How's your beer?" I hadn't even touched the one I had and let him know. He returned to the couch and sat back down taking a drink at the same time. He reached for his cigarette purse and flipped it open. "Sorry but I need another one." he said and pulled a fresh cigarette out. "You're not bothering me, promise." I said then added more, "I'm kinda diggin it, keep going". He smiled then lit the cigarette. While exhaling he started again. "Okay, where was I? Oh yeah, Michelle working the night shift. So she's been on the night shift now for 3 months and during that time I've nearly perfected who Jenn is. I've felt so comfortable as Jenn that I would make trips out dressed up, mainly to gauge the reactions of others. Would I pass or not? The answers was yes and there was no doubt about it. I mean, look at me Will, do I not look like a genuine woman?" The question was rhetorical, he continued. "This all led me to tonight. I can't keep this in anymore, it's driving me crazy. I need to let someone in on my secret and the only person I felt that I could trust was my best friend, that's why I'm here now." For the first time he took a drag facing me, I hoped this meant he was loosening up. He dragged on the cigarette, took it away from his mouth, and then exhaled to the left so the smoke wouldn't get in my face. He looked at me, "Are you okay? Have I freaked you out yet?" He hadn't and I let him know. "You're good. I'm still here, you're still here. Keep going." He immediately brought the cigarette back up to his lips and snapped dragged the cigarette. It was then that I realized that I wasn't looking at Jimmy anymore, I was staring at Jenny. I couldn't help but think of him as a girl, not with what I had going on down below. I'm a straight guy staring at this beautiful, young woman. Jimmy's Jimmy, I'm here talking to Jenny. She exhaled and started to talk. "I have to express more of myself, more of Jenny, and I feel the only way this could be possible is to let my best friend know who I am. I can't tell Michelle, she wouldn't understand. I mean, that's sounds like the logical thing to do though. Make my girlfriend understand and become besties... both you and I know that'll never happen. Michelle's too vein, she couldn't handle me looking better than her." She was right, her looks blew Michelle's away. She kept going, "I mean, don't get me wrong Will, I'm not suggesting we shack up. All I'm saying is this had to get out and the one person I need to understand is you. I can't lose you as a best friend. The truth is..." She paused and took her last drag off of the cigarette. She was smoking quick but only smoking a little more than half the cigarette. She leaned to the ashtray and exhaled at the same time, snuffing the cigarette out. "I need to end it with Michelle. There's no future there." She seemed to be vague all of a sudden. "Do you understand what I'm hinting at?" She asked me. I answered, "Ummm... are you saying... shit, I don't know how to put this." She interrupted, "Here, let me help you." Again, she reached for her cigarette purse, I wondered why this girl didn't just smoke the whole thing? I assumed she was nervous and that's the reason for chain smoking. I let it go, the images that it was producing were worth it. She lit the cigarette and returned the lighter to its case, letting the cigarette just hang there. It dangled there for a couple of seconds and then the cigarette sprang up and the cherry burned bright. She was facing me straight on and past the cherry and the smoke I could see her cheeks hollow as she sucked on the cigarette for dear life. Jenny went right back to our conversation. "Uughhh" she groaned, "Do I like girls or boys? I guess that's what we're talking about, right? That's a hard one... I'm not sure I know how to explain it." She instinctively took another drag, no doubt trying to relieve the stress. She had something to say and didn't want to say it but went on anyway. "Well. I've been with girls, that's obvious. Did I like it?" She scrunched her face and leaned to her right. "Not really. So why'd I do it? It was what was expected of me I guess. I don't know..." Back to the cigarette and then to me again, "Have I ever been with a boy? I haven't... EVER. Do I like boys? Ummm... One in particular. Don't get me wrong, I love the attention men provide to me. There's a certain feeling when a good looking guy check's me out. It makes me feel good, let's me know I'm doing things right." Another drag, another exhale then back to talking. Her voice isn't whispery anymore, now it's smoky. "Do I want to go out and fuck every guy that pays attention to me? NOT AT ALL." She emphasized. "Like I said, I'm attracted to men but one in particular. I'm in love with you Will." She let that hang there, let me soak it in. "I'm sorry." she added. Again, a tear started down her cheek from behind her glasses. I reached up and whipped the tear away, this time letting the back of my hand graze her cheek in a petting sort of a way. She made a nervous little laugh and in a very girly girl way asked, "What's going through your head right now?" She brought the cigarette to her lips, it was now short with about two drags left on it. She held it there, squinted and inhaled. She waited for my answer, protruded her lower lip and blew the smoke straight up. I said the first thing that came to mind. "I wanna play with that curl." I said as I pointed to the left side of her face. She giggled and said, "God, I love ya." She leaned to her right still facing me and took the last drag. She reached out without looking and put the cigarette out. "I started smoking for you by the way." I hadn't expected that and had to ask, "What do you mean?" Without hesitation she started to explain "We had that conversation, I know you remember it, that night we got drunk and talked forever. I lied but I know you didn't, you said you like girls with ringlets that smoke. You mentioned glasses too, luckily I'm blind. Anyway, about a month later I was able to dress up, and when I did I had one of Michelle's smokes. I took pictures and I knew I needed to work on it. The smoking didn't bother me, hell I already chewed, but now I love it. I love my cigarettes and even if you left, I'd still smoke." "And the hair..." She took her right hand, cocked it back as far as she could and patted the bottom of the curls. They sprung up and down, she knew what she was doing. "The night I smoked was the first time I curled ringlets into my hair. I've done it 100's of times since, I sorta get off on curling my hair in a mental sort of way. Not that I wanna fuck myself but I always find myself wondering what you'd think of them. She scooched a little closer to me and turned a little to her right. "Here, give me your hand." She motioned to my right hand. I raised my hand and she grabbed it with her left hand. She moved my hand to the curls I had pointed at, "I made them for you, play with them all you want. Don't be afraid, you won't mess them up." My hand was now in her hair. I shot my gaze to that area searching for the most defined and stiffest curl. Once I found it I started to play, pinching it and rubbing the strand between my thumb and index finger. I was rock hard and I wanted her, I wanted to throw her down, kiss her and make love to her but I resisted. She moved her left hand to my right leg and rubbed it up and down. She didn't intend this in a sexual way and I knew this. She spoke without moving her head not wanting to interrupt where I was at, "Would a cigarette make things better? They're close to me so I barely have to move." There was nothing more that I would have liked and told her so. She leaned a little to her right reaching her right arm out to grab the pack of smokes. As she did this, her hand slid up and rested on my rock hard penis. She didn't know what she was touching, I know she lost focus and I didn't know what to say. Before I could say anything her thumb started back and forth over the ridge that separates the head from the shaft. It was like her fingers were on auto pilot, they found a ridge and decided to investigate. She pulled her hand away still not knowing what she had done. She needed the hand to get the cigarette out and started fumbling with the case, still without looking down. As soon as the smoke was free from its case she brought it to her lips with her right hand and returned her left back to the ridge. It was like her hand had found a comfortable spot, she started flicking the ridge again. It was more like a nervous movement, like when a girl plays with her hair or when a child plays with the edge of their blanket to get to sleep. With her right hand she lit the cigarette, tossed the lighter to the side, brought her hand back up to the smoking cigarette and inhaled deeply. When satisfied that she had had enough she exhaled straight out. As she did this, without thought, she stopped the flicking and grabbed on to my dick like it were a railing and she was falling over. It wasn't a death grip but was enough to make me squirm a little in my seat. As soon as I moved she realized what was happening and whipped her hand off of me. She brought it to her mouth, kind of covering it like she were in shock and said, "Oh my God Will! I'm so sorry. I didn't know I was doing it. I swear." I stopped playing with her hair and brought my right hand down to her shoulder, "I know you didn't. I didn't know how to stop you though. Besides... it felt great." She replied quickly, "My god, if that was your penis, I can't wait to see it. How long was I holding it?" I smirked at her whit. Laughingly I said, "Well... you were holding it for only seconds but you were rubbing it for close to a minute." I moved my hand back to her hair and pinched a large curl several times. "I'm so embarrassed" she continued. As she said this I shifted my hand to her neck, cupping it like I were gripping a small tree stump. The curls rested on the back of my hand and I started to massage. She brought the cigarette up for another drag and I waited. Still massaging I waited until she exhaled and then turned her head towards me and I made my move. I moved my face towards hers and she instantly knew what I was doing, moving towards me she returned my advance. Our lips met and I shot my tongue in to her mouth, she accepted. Our tongues twisted over one another, back and forth. After seconds I pulled my tongue from her mouth and hers quickly entered mine. I sucked on her tongue a few times and could taste the cigarette. I didn't mind the taste, the pros outweighed the cons. What surprised me more was the tongue piercing in her mouth. I instantly recoiled and gave off the perception that I didn't approve. She knew exactly what had happened and said, "Oh no. You don't like it? I can take it out..." I started to shake my head and said, "No, no, it's not that. It's just... I hadn't noticed it, I couldn't tell. It was a surprise to me, that's all. I actually kind of like it." She flashed me a sly grin and said, "My nose is pierced too." She pointed to a tiny spot near the crevice on her left nostril. "You can barely see the hole and I hardly ever where it. I got it way back before I even met Michelle. That summer I went to my cousins in LA. I did it as 'a dare', she did the air quotation marks with her fingers, "Truth is I couldn't wait to get it but I had to play it off like I hated it. I didn't put it in tonight cus I wasn't sure you'd like it?" She ended the sentence like she were asking a question instead of making a statement. I sighed and said, "Fuck. That would be hot. Can't wait to see it." She smiled knowing what I really said was 'Jenny's welcome back'. I twisted my hips towards her and sort of slumped into the corner of the couch. She took another drag off of her cigarette then exhaled, she turned to face me holding the cigarette in her outstretched fingers. She moved her right leg on top of my left and rested some of her weight on to my left side, laying half on me. She moved back in for a kiss, resting the hand with the cigarette on my left shoulder, just above my heart. We started kissing again, this time even more passionately than before, if that was even possible. After a minute or so of this she broke this kiss, turned her head to the side and took another drag. Her motions were hurried, her curls dangled in my face. She exhaled half the breath and turned to lock lips with me again. We embraced, her lungs still half full of smoke, needing to breath, she exhaled through her nose. She adjusted her weight and moved the hand with the cigarette towards my crotch. I could see everything as she took her ring finger and her little finger and started to scratch my dick, still holding the half cigarette straight out. The bulge in my jeans stood out as she again broke the embrace. She looked at the hand in action, stopped and sat up, took a drag off of the cigarette, put it out and started pulling at my waistband with both hands. With the pants pulled down to my ankles she spread my legs and moved between them. "My god, it's big" she said as she bent down and started kissing it. Having measured my penis before for 'fun' I know it's about seven and a quarter inches long. What women mostly like about it though is its thickness. As I watched her kiss me I moved my hands to the sides of her head and played with her curls. She stopped kissing and positioned herself over the tip of my dick. Before letting it enter her mouth she said, "I've never done this before, you're my first." With that, she put her lips around the head of my penis and sucked only the head, rubbing the piercing back and forth finding the right spot. I was in ecstasy and after several sucks she plunged down taking in three quarters of my shaft. She stopped and then bobbed up and down many times. She removed her mouth from me and brought her right hand up, starting to jack me off. She spoke, "I don't want you to come yet. I have plenty of time to taste you." She looked at me, "I want you to cum inside me and I don't mean my mouth." She reached for my hand and stood up. "Come on, let's go to the bedroom." I took her hand and she helped me up, once up, I pulled my pants up as fast as possible. She turned and kind of pranced towards my bedroom, reaching her right hand back to me, I grabbed it and followed closely as we headed towards the kitchen and ultimately my bedroom. I watched her ass and her hips sway as we glided halfway through the kitchen, every movement an intoxicating image I won't forget. Still to this day I don't know what came over me, I had never done anything like this before, but I stopped dead in my tracks. I had spotted the kitchen table and as soon as Jenny stopped I moved towards her, gripping her hips from behind with each hand, I moved her towards the table. When we reached the table she stopped and I moved my hands from her hips to her boobs. I don't know how it was done but they felt real and I began to massage. We stood touching, my front to her back, she cocked her head to the side as the curls fell her neck was exposed. I sucked on her neck while moving up and down, her hoop earring getting in the way occasionally. "I can't wait," I said breathing heavily. "Ohhhh, Willlll," she moaned, "Fuck me now." She didn't have to say anymore as my hands slid down her flanks and made their way to the button that held her pants closed. I fumbled with it for a second and then got it. I moved the zipper down and noticed how short the zipper was compared to men's jeans. With that done I moved my hands to her hips and started to pull down. The Capri's were tight and she did a little wiggle to help out. Eventually they slipped down revealing a black lacy thong. I smiled and left the Capri's to fall and stay around her ankles. I yanked my pants back down and started rubbing my manhood between her still covered ass crack. She moaned again and then said, "I didn't have any amyl's, that would've helped. I brought lube though. We can still do this." Without waiting for me to answer she moved her feet in cute little steps, the Capri's still around her ankles, and moved the few feet to the kitchen counter, grabbing her purse. She opened it, quickly removed a small clear bottle, then made her way back, turning towards the table once she got there. She whipped her thong down and in one quick movement grabbed the bottle and squirted a dab out. As she reached around and applied the lube to her hole, she started to talk. "Remember, you're my first. My holes a virgin so please go slow." With this she gave the bottle a hard shake and squirted another dab into her hand. She reached back and found my cock then wrapped her hand around it and moved it up and down. We were both lubed up and ready to go. I put my hands on her hips and moved close as she bent slightly forward. I moved my right hand and took hold of myself with two fingers and then guided towards her hole. I found the hole and applied a little pressure, she moved her butt towards me willing to accept whatever was about to happen. I leaned forward, increasing the pressure when she suddenly thrust back, jamming me inside of her. Instantly she leaned forward, resting her elbows on the table, she let out a little yelp. We both froze somehow knowing what to do, she tried to relax and I let her. I moved to kiss her neck and put her at ease, the movement made her flinch. I started kissing her neck and after about thirty seconds she started moving her hips in a thrusting motion. "You're inside of me Will. I want you to cum inside of me. Please... make me your girl." I started to match her rhythm still not believing what was happening. My hands rested on her hips and I stood straight up while she still leaned on the table, her hole now loosened and willingly took me in. After minutes of pumping in and out I stopped, "Can we reposition? I want you on the table." I asked. She nodded and I stepped back letting my dick slide slowly out of her. She removed one foot from her Capri's, swung her right knee up and onto the table, gave herself a little hop and was now kneeling. Without having to ask, she moved her hips so they lay flat on the table, twisting her torso and positioning her ass to me, legs up in the air, Capri's hanging from her left foot. I took the pants off of her ankle and moved the backs of my hands to her inner knees. She spread her legs and I reached for her hips. I grabbed hold and slid her to me, her ankles making their way past my ears, her calves rested on top of my shoulders. She took her hands and spread her cheeks so I moved in. Her head was cocked in an uncomfortable looking position, she wanted to see me enter her. I moved then paused as the tip of my dick touched the rim of her hole. She was still wide open down there, the hole still looked to be the same size as I was. I looked her in the eye and she gave me a nod letting me know she was ready. There was a little pressure and then it just seemed to give way. I was deep inside of her, as far as I could go. She moaned approvingly and I started my motion. She laid on her back and propped herself on her elbows. She watched as I went in and out, her private parts seemed to be covered by a small patch of tape but I could tell she loved what she saw. She threw her head back and shrieked, "Oh GOD!!!! I think I'm gonna cum!" I slowed down and she looked at me like a woman possessed by the Devil then asked, "Are you close? Don't slow down." It came out as a half cry mixed with a plea. I sped back up as her hand darted to her crotch, she grabbed at the patch and made a tearing motion to her right. Her dick sprang out of the side of the patch, it was so small it was cute. I had never seen another dick in person and certainly had never looked at one and thought it was 'cute'. I couldn't tell if she was half hard or if that was as big as it got. She started shrieking loudly, "Yes, yes, yes, yes..." and then one final, "UUUhhhhhh......." I continued pumping as her dick started spurting cum onto her hip and the table. She moaned and then looked at me, the spurting finally stopped and her dick stopped twitching. Without hesitation she reached her left hand to where the cum sat on her hip and swiped a dab up with her pointer finger. I was still pumping strong watching this whole scene as she moved her finger to her mouth, wrapped her lips around the base of her finger and pulled it out. The finger was now clean, she swiped another dab off of the table and sucked it clean again. The site of this final swipe made me lose all control, as I came for the second time tonight. "There you go..." She was still breathing heavy, I still rested inside of her. "You came inside of me" she said, still propped on her elbows. "You made me your girl." I slowly pulled from her, my dick flopping down as soon as it cleared the rim. "Sleep with me?" I asked as I reached for her hand. She sat up and then popped off of the table. Wearing only her halter top and her heels, she stood next me, I seemed to tower over her. I led her back to my room and she climbed into my bed. I turned on the bedside light and turned off the main light then made my way to the bed. I climbed in and snuggled up to her, she had rolled on her side so her butt was facing me. I wrapped my right arm under her and my left arm over her then brought my crotch up to her butt so we could spoon. I felt a wet spot where her hole was and asked if she was okay and if she needed to clean up. She was holding my left hand close to her chest, she still wore the halter top. She shook her head no then whispered "Not tonight. Not this time. I just wanna fall asleep like this. With my man holding me, his seed inside of me." I nestled my face in her curls after giving her a kiss on the cheek and saying good night. She whispered one last thing before falling to sleep. "Thank you for this Will. It's all I've ever dreamt of. I can't wait for tonight's dreams. I love you......." To Be Continued...