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The Tomboy

A true encounter dressed up a little bit for reading purposes

This story is dedicated to my great friend BobbyLynn.

I met Bobby when I was 18 and she was 9. I had just moved to Ohio from North Carolina. I was living with my older brother in his little two bedroom house. I had just graduated high school and was planning on going to the local Tech school to take auto mechanics. I already knew quite a bit about cars and spent most of my free time working on them.

My brother, Todd owned his own auto shop and was letting me work for him doing what I did best.

I was outside in my brothers garage one sunny July day. I had the garage door open and was buried under the hood of my car when I heard a small voice. “What’s wrong with her?”

I turned around and there stood a little boy in a Cincinnati Red’s shirt and a baseball cap turned around backwards. He had dark brown hair and vibrant blue eyes. When he smiled you could see that one of his front teeth was just starting to grow back in from where he lost his baby tooth.

I smiled at him. “Well, there’s not really anything wrong with her.” Referring to my car. “I just like getting under the hood and tinkering around. I was thinking about changing the oil, but I’m not really sure I want to get all dirty.”

The little boys eyes brightened up. “I’ll do it for ya. I’m pretty good at changing oil. I can do lots of things with cars. My uncle taught me. He is a master mechanic.”

I couldn’t help but smile at the little boys enthusiasm. “What’s your name kid?”

“I’m Bobby. I live right next door. You must be Jon, Todd’s brother. Todd can tell you how good I am at working on cars.”

I smiled again. I had always been good with kids and I was really starting to like this little boy. “I’ll tell you what Bobby. I’ll let you help me. How about that?”

“Well that’s fine with me, but I’m afraid you will just get in my way. How about you just let me do this and you can watch so you will feel better about it. I know you are afraid I’ll screw it up.”

I chuckled at him. “Alright Bobby. I guess if Todd will recommend you I’ll give you a chance.”

I sat back and watched this little boy get down and step by step change the oil in my car. I was blown away. He did it in record time and came out cleaner that I ever had.

“Wow kid, that was amazing. You will be a great mechanic someday. Hell, you are a good mechanic now. How old are you?”

He smiled at me. “I’m only 9 years old. I can take my bike completely apart and put it back together without any help.”

I laughed at him. “That is impressive. I’ll tell you what, from now on when I need my oil changed I’ll come and get you. I’ll even pay you to do it.”

“Wow, thanks. Todd pays me $5 to change his. How much are you gonna pay me?”

Damn. I could change it myself for free, but I couldn’t be outdone by my brother. “I’ll pay you $7.”

“AWESOME. I’m gonna go tell Mom. I’ll have enough money to buy that Super Man comic in no time now.” He turned and ran back through the hole in the chain link fence to his house.

I couldn’t help but smile. I remembered being a boy that age once.

Later that evening I was getting ready for dinner. My brother came in and told me supper was done. I walked downstairs and joined him in the kitchen. “That little neighbor boy came over today. Impressive kid.”

My brother gave me a funny look. “Neighbor boy? Who?”

“The one right next door here. I think he said his name was Bobby.”

My brother smiled. I didn’t understand what was so funny. “Neighbor GIRL, Jon. Bobby is actually BobbyLynn. HE is actually a SHE. She is just a big tomboy. Her mother hopes that she will grow out of it, but I have my doubts. That girl can outwork most of my guys at the shop. She is amazing under the hood of a car. She can listen to an engine and tell you what’s wrong with it.”

I was blown away. I couldn’t believe that Bobby was a girl. I mean he, she, looked just like a little boy. “You have got to be kidding me. That is a little girl? God I hope she grows up to look more like a girl. I see a hard future for her if she doesn’t.”

Todd laughed at me. “Well I’ve seen her all dressed up for church. She hates it, but her mom makes her wear a dress. She looks like a little girl then. I’m sure it was just the hat and short hair that threw you off.”

As the years passed I watched Bobby grow. She never outgrew her tomboy ways. As she got older she became more a more efficient mechanic and was really active in sports. Many times she and I would play basketball and I would always get my ass kicked by her.

She had an older sister named Catlin. She was about 6 years older that Bobby. I would have thought she was hot, if it wasn’t for her being such a bitch. She was always making fun of Bobby for being so boyish. She would tell her that she looked like a dyke and would tell her that she was going to grow up to become a lesbian. It would make me mad, but it never seemed to bother Bobby. She would always just roll her eyes.

Bobby had become like a little sister/brother to me. We would hang out and look at car magazines and play ball and work on my car. When she turned 16 my brother gave her a job at the shop. He was right, she could outwork any of the guys there.

She still looked like guy in many ways. She had colored her hair black, and kept it cut really short. She always had her trademark hat on backwards. She always wore baggy boys clothes and tennis shoes and never wore makeup. If you looked really close she looked like a girl. She had feminine features, almost fairy like, but the way she dressed just made her look like a pre-pubescent boy. Even if she did dress like a girl, she wouldn’t have really needed make-up. She had bright pink lips naturally and her eyes were always bright and lit up.

It was a Saturday night late in August and Bobby and I were the only ones in the shop. Bobby was 18 now and I was 27. I had stayed late to do some paperwork for my brother and Bobby had spent the most of the day working on a transmission for Mrs. Madden, the local town whore. I walked out of the office and looked at her hovering over the transmission spread out on a table. She was expertly rebuilding it. “Hey Bobby, I’m heading out. Do you want a ride or will your mom be picking you up?” Bobby was 18, but had gotten in trouble for drag racing and had her license suspended. She was going to be able to test for them again in a few weeks.

“Actually, I’m going to stick around here and see if I can’t get this finished up. Mrs. Madding is going to be here early in the morning to pick up her car. I’ll probably be finished in about an hour so I figure I’ll just go ahead and finish tonight instead of having to get up extra early in the morning.”

I looked at her with a doubtful look. She was almost done with the transmission and I knew it wouldn’t take her another hour to finish. I thought that maybe she was going to sneak a guy in. I had never seen her with a guy, but she had always been one of the guys around us, so I didn’t think she would really want to share that kind of information with us. I decided to just let her be. “Well that’s fine. Make sure you lock up when you are done. You don’t really need to walk home that late, so when you get finished call me or your mom to come and pick you up. Are you still wanting me to take you on the driving test course tomorrow?”

She smiled at me. “Yeah sure. I think I’m going to go Wednesday to get the papers from the judge. I should be able to test again after that..”

“Alright, if I don’t see you tonight I’ll see you tomorrow.”

I walked out and got in my car and drove home.

When I walked in the door my brother was sitting on the couch. “Hey bro. Did you remember to bring home my tool box? I’m suppose to work on Bobby’s car in the morning.”

Bobby’s mom had bought her a car. The body of the car was perfect, but it wasn’t running yet. Todd had agreed to fix the car so that Bobby’s mom could surprise her with it when Bobby got her drivers license back.. “Fuck. I forgot all about it. I’ll go back and get it.”

“Thanks man. I wouldn’t ask you to, but Clair is on her way over and you know how she gets if I’m not here and I really need the tools. Bobby is going to be able to get her license back soon, so I really have to buckle down and get it done.”

I walked out the door and drove back to the shop. As I pulled into the shops parking lot I noticed a car sitting there. All the lights were off in the shop with the exception of the employee break room upstairs. I thought back to how Bobby had acted when I left. I wondered if she did indeed invite some young guy here and I wondered what they might be doing in the break room. I was surprised at the ting of jealousy I suddenly felt. She was like a sister to me, I should be happy for her if she was happy, but what if it was just some young jerk trying to take advantage of her. I convinced myself that that was the case. I told myself that she had fallen victim to some young mans bull-shit lines and was getting ready to mess her whole life up. That was the only way I could rationalize the feelings I was having about her being up there with someone.

I crept up the stairs. I didn’t want to give them a pre-warning to my arrival. No, I wanted to catch the bastard in the act so I could kick his young ass for taking advantage of this helpless girl. She was no where near helpless though and I knew that, but I was just looking for an excuse to beat the shit out this guy.

I was in the hallway just a few feet away from the lounge. I could hear moaning and heavy breathing. “Fuck, I’m already too late.” I thought to myself. I closed the last few feet between myself and the lounge door. I looked through the window just as I reached the door and I couldn’t believe what I was seeing.

“Is that Bobby?” I thought to myself, because what I seen before me was one of the most beautiful girls I’d ever seen in my life. It was Bobby. She was naked sitting on the lounge table with her legs spread wide and each of her feet resting on the back of a chair. She didn’t have her hat on. In all the years I had known her I had only seen her without the hat a hand full of times. Between her legs was a woman with long silky blonde hair. I couldn’t see her face, I could only see that she was eating Bobby’s pussy as if it was her last meal. Bobby had her head thrown back and she was thrusting her hips forward.

I stood there and stared. I couldn’t drag my eyes away from what I was seeing. It wasn’t the fact that there was a woman sitting there eating Bobby’s pussy. It was Bobby herself. I had seen Bobby everyday for the last 9 years. I had watched her grow from looking like a little boy to looking like a little man, but now looking at her very feminine body I couldn’t help but get an erection.

She wore baggy clothes everyday and when she was at work she wore the work coveralls. I would have never thought that she had the body of a goddess. She didn’t have very large breast, they were maybe a b-cup, but they were firm and round and flawless. Her skin looked as if it was as smooth as silk and her legs were long for her 5 foot frame. Her body tapered in at the waist line and then flowed back out into her hips. She looked better than any porn star that I had jacked off to in the last 10 years.

I watched as the lady between Bobby’s legs took her hand and slid a finger into Bobby’s pussy. Bobby moaned and thrust her hips harder. She started panting faster and faster. I could see that she was getting ready to cum.

“Oh, Janet. I’m going to cum. Please don’t stop.” She still had her head tilted back and her eyes tightly closed.

Janet? As in Janet Madden? I couldn’t believe it. She was at least 35 years old. She was hot for her age, but so much older than Bobby. She was married. I had heard of her sleeping around with several men, but never another woman. How long had this been going on? How did she seduce Bobby?

I looked in and watched the woman stand in front of Bobby. She still had her finger deep in Bobby’s pussy and she was fingering her hard and fast. She leaned over and kissed Bobby.

“Cum for me little girl. Come on. Tell me how much you love this.” The woman was cupping her whole hand over Bobby’s little bald pussy. She wasn’t pulling her fingers in and out of her pussy now, she was holding them inside her and moving them up and down so that the palm of her hand would rub Bobby’s clit.

“I’m…. Oh god,…. I’m going to cum… OH FUCK. Ah.. Ah ah ah ah ah… yes.. I love it, fuck me with your fingers.. Yes yes.. Here it comes… ahhhhhhhooooooooo..”

I watched Bobby’s pussy contract around Janet’s fingers. She was still thrusting her hips forward. She grabbed the back of Janet’s head and pulled her in for a kiss. “That was fucking amazing.”

Janet smiles at her. “You weren’t so bad yourself. Now, I need to get going. My husband is going to wonder where I am. We can’t have him find out about our little secret now can we. You will keep your mouth shut about this won’t you Bobby?”

Bobby smiled at her. “Now Janet, why would I tell anyone? You held up your end of the bargain.”

Janet frowned. “We’ll stick to the deal. Although I can’t help but feel like I made a deal with the Devil.”

I wondered what they were talking about, but just as the thought crossed my mind I realized that Janet was getting ready to walk through that door. I hurried out of the hall and ran into my office. My cock was so hard it was hurting. I sat down in my leather desk chair and pulled out my cock. I had to deal with this now or I would have blue balls.

I started stroking my cock slowly. Then as I thought about Bobby’s glorious body I started stroking faster and faster. I tried to convince myself that the reason I was so turned on was because I had just witnessed two women having sex and that it had nothing to do with an eighteen year old girl, but I couldn’t even remember what Janet’s body looked like. I could tell you every angle, mole and freckle that graced Bobby’s beautiful body. I wasn’t turned on by watching Janet finger Bobby. I was turned on simply by the fact that Bobby was getting fingered. I wanted it to be me. I wanted to be the one to finger that beautiful pussy. I wanted to lick it and suck it and fuck it and I hated myself for it.

I felt like I was betraying Bobby somehow, because I had always been a brotherly type to her and now I was lusting over her. I knew I could never let her know how I felt. She would feel uncomfortable around me. I was nine years older than her and even though she was just with a woman older than me, it was still different than having a man that’s older. Besides that, apparently she’s a lesbian as well and wouldn’t want me in return. Of course I was still trying to convince myself that I didn’t really want her like that.

I was deep in thoughts of Bobby as I felt my balls tighten up against my cock. I could feel my load rush from my shaft and fountain out of the head of my cock. I had never came like that before, especially by masturbating. I grunted, with my eyes tightly closed. I didn’t want to get too loud, because I wasn’t sure Bobby had left yet. I got my answer.

From the hallway I heard Bobby. “Jon? Is that you in there?”

I quickly pulled my pants back over my cock and tried to clean the cum off of my shirt and pants before she got in the room. “UH… Just a… Yeah, it’s me Bobby.”

Bobby opened the office door. “Hey, I was getting ready to walk home and seen your car outside. How long have you been here?”

I didn’t know what to say. “Well I just came up the steps a few minutes ago, but I’ve been here about 15 minutes. Why?”

“Oh no reason. I just didn’t hear you come in. What are you doing here?”

“I came to pick something up for Todd. Do you need a ride home?” I regretted it the moment I said it. I couldn’t be alone with her right now. I don’t think I could trust myself with her alone. I couldn’t get her naked, and very much female, body out of my head. She would sit in the front seat with me and every time I looked at her I knew that is what I would see.

“Actually I’d love a ride home. You wouldn’t care to stop by the store would you? I need to pick a few things up.”

I laughed a dry laugh. Of course she needed a ride home. Figures. That was just my luck. “As long as you aren’t going to buy tampons or anything like that.” Yet another thing I regretted as soon as I said it. I had NEVER acknowledged her as female before. I had always treated her like one of the guys. We never talked about her female cycles or anything like that. It was one of those things that we avoided at all cost. I mean sure I knew when she was having her period, because I knew the mood swings and the look on her face when she would have cramps, and of course there was the fact that she would empty a bottle of Motrin within a weeks time at least once a month and the frequent trips to the restroom during that week.

She looked at me with suspicion all over her face. “I’m not. I’m just going to get something to pack for lunch tomorrow.” Her eyebrows were furrowed and she didn’t look amused at my poor attempt at a joke. She knew something was up, she just didn’t know what that was just yet.

“Okay then, lets get out of here.” I walked past her, hoping she wouldn’t notice the white cum stains on my pants and shirt. I grabbed Todd’s tool box on the way out and walked to the car. The whole way to the store I kept glancing over at her. I couldn’t see her as one of the guys now. Every time I looked at her, just as I knew I would, I couldn’t help but see that beautiful girl that was on the table in the lounge. I found it impossible to talk to her. I had never had trouble talking to her before. We would talk about cars and engines and things like that and where we were going to play ball and who with. Now I felt awkward as if I was talking to a stranger.

I could tell I was making her uneasy by not talking to her, but she never said anything about it. Finally she did speak. “So are you going to tear that motor down in that Nova tomorrow? I can help if you want me to.”

Any other time I would have gratefully excepted her help. If I were honest with myself she was ten times the mechanic I was, but now I was talking to a girl and I felt like she shouldn’t know about cars. “Ah, I’ll probably start it Monday. I should be able to handle it on my own.”

I seen the hurt look come across her face. I hated myself for it. I was having feelings for her now that I knew better than to have. She just turned her head and stared out the window.

I pulled into the parking lot at a little gas station that we frequented. It was the same place we would always go to and browse through muscle car magazines. We would sit there for hours and look at all the car mags and then buy them all and take them to the shop and look at them again.

“Hey do you want me to pick up that Special Edition Muscle Weekly? It’s suppose to be pretty bad ass.”

“Uh.. Yeah.. Sure. You can grab it if you want to. I mean you don’t have to I can get myself a copy tomorrow.”

She gave me a dirty look. “Jon, we always look at that magazine. Why wouldn’t I want to get it? You know I love it as much as you do.”

“You’re right. Just grab it and I’ll give you the money back.” This was also a mistake. She and I would always pick things up for each other and never pay the other back. It wasn’t expected and we didn’t offer or even ask for the money, because we knew that somehow it would always break even.

“What the fuck? Are you pissed off at me or something Jon? Because you are really acting weird.”

“I’m sorry Bobby. I’m just a little aggravated at Todd. It’s nothing.” Even this was a mistake, because if there had ever been a conversation like this before I would have handled like as if I were talking to a guy. I would have said something along the lines of “Shut the fuck up and hurry.” Or “Fucker if I was pissed at you, you would know it.” but that isn’t what I did. I gave her an explanation. Men didn’t do that. They didn’t feel the need to explain things to each other. I shouldn’t have explained anything to Bobby.

She slammed the door and went into the station. I watched her ass for the first time in all the years I have known her and I could feel my cock getting hard. She was wearing baggy jeans, but you could see that her ass was just a little bit too round to be a guys, even in the baggy denim that covered it. I found myself wondering if she wore panties and if so what kind? Were they sexy? Did she wear lace? Or did she wear men’s underwear like me. I chastised myself for thinking that way. I didn’t want to think of Bobby like this. I wanted it to be back the way it was before, but I would never be able to get that image out of my head of her sitting on that table with her legs spread wide. Her beautiful breast bouncing with each thrust of her hips. I didn’t even know she had breast until tonight.

She came out and got back in the car without saying a word. I drove us home and she threw her hand up as she walked up her sidewalk to her house.

I took Todd’s tools into the house and sat them in the kitchen. Todd was already in bed and I could hear him banging the hell out of his girlfriend. That was the last thing I needed at that moment. I knew I wouldn’t be able to sleep so I did what I always do when I’ve got a lot on my mind. I went out to the garage and lifted the hood of my car.

I tinkered around with this and tightened that. I tested a few things out that I knew were in working order. No matter how much I did to keep my mind occupied it kept going back to her. I finally got frustrated and threw a wrench down on the floor of the garage. It tinged and scooted across the garage floor.

“You know abusing your tools won’t help your problems.”

I spun around and there stood Bobby. For the first time in seven years I didn’t see that little boy standing there in a Cincinnati Red’s shirt and a ball cap on backwards. Instead I seen a woman. A beautiful girl with short spiky hair. She was wearing a pair of running shorts and a loose fitting t-shirt. She wasn’t wearing any shoes and for the first time I could see how small and dainty her feet were. She didn’t have her usual hat on either. Her hair was messy, but cute. It framed her fairy like face just perfect. She was astonishingly beautiful. I couldn’t find any words to say to her. I could only sit and stare.

She spoke again. “I went home and tried to figure out why it was that you were acting so strange. I racked my brain trying to figure out what I had done to make you mad.”

To me this was completely new. I just realized that even though she was a tomboy, she still thought like a girl. She still got her feelings hurt when she thought that someone was mad at her. She would dwell on it just like very other eighteen year old girl in the world.

“I replayed everything in my head that was said today between you and I. I couldn’t come up with anything that I said that would have offended you. Then I figured it out.” She dropped her head and wouldn’t meet my eyes. “You saw me tonight didn’t you? You say me with Janet.”

I didn’t know what to say. “Bobby… I… I’m sorry. I didn’t mean…”

“No, I’m sorry Jon. I shouldn’t have done that. I was just confused about a lot of things and I thought that would answer some of my questions. I walked in on Janet sucking her pool man’s cock and I made a deal with her that I wouldn’t tell her husband as long as she would help me figure out my own sexuality. I had noticed the way she would stare at me and even flirt at times. I knew she was curious about me.

I have lived my whole life like a guy. I have done guy things and dressed like a guy and then all of a sudden I start developing like a girl and I start having feelings for a boy and I didn’t know what to do with all these emotions I was having. And all these years with my sister telling me I was going to be a lesbian, I just had to know if I really was.” She took a deep breath and looked up at me for the first time. “Jon I’m not going to sit here and lie and say that I didn’t enjoy what I did with Janet, because I did, but I also know that it was just a one time thing. I know I’m not a lesbian. I know that what I was feeling for y….. for this guy was real and it wasn’t just me confusing friendship.”

Again I was at a loss for words. She had never talked to me like this before. The deepest conversation she and I had ever had was over what football team we would like to see win the Super Bowl.

“Bobby. I … I don’t know what to say. I mean I wish I hadn’t spied on you, but when I looked in there I couldn’t look away. I ….”

“Why? Why couldn’t you look away? Was it because there were two women having sex?” She sounded mad and hurt. “Was it because it was every man’s fantasy? Did you get your rocks off Jon? Did it make you happy to see some girl eating another girl’s pussy?”

“BOBBY stop it! You know me better than that. Have I ever given you the impression that I would like something like that? You have met the girls I have dated. Did any of them seem like they would be like that? For God’s sake that wasn’t what it was at all.”

“Then what was it Jon? Why couldn’t you stop looking? Why did you keep watching? Did you break out your cell phone and take some pictures? Answer me Jon?”

She was throwing more questions at me than I could think about. I was getting confused and frustrated and before I even thought about what I was saying I said “Because I’m crazy over you Bobby. Because I thought you were beautiful. For the first time in all these years I seen you as a woman and not a tomboy. I couldn’t take my eyes off of you Bobby. It had nothing to do with Janet being there. Hell she was in my way. I’m sorry I watched, but my God, you are beautiful.”

I watched a surprised expression come over her face. “You think I’m beautiful?”

“Bobby, I have cursed myself this whole night for the thoughts I was having of you. I knew that nothing would ever be the same after tonight because I could no longer look at you as if you were just my tomboyish little sister. I knew I would never be able to look at you again and see you as one of the guys, because weather you like it or not BobbyLynn, you are a beautiful girl…no strike that, you are a beautiful woman. I know I’m too old for you, but I am still a man and I know a beautiful woman when I see one and Bobby, you are the most beautiful creature I have ever seen.”

She walked towards me, closing the distance between us. When she was finally standing right in front of me I was afraid she was going to punch me, because she didn’t slap people like most girls. She punched, but what she did surprised me even more. She wrapped her arms around my neck and whispered in my ear.

“Jon, I have been thinking about you for a long time now. I tried to convince myself that it was just a girly crush, but it’s not. I don’t care how old you are. I know how I feel and I know you better than anyone else and you know me just as well as I know you, so you know that when I tell you that I want you that I mean it. I want to be with you Jon. I’m tired of being one of the guys ……at least with you I am. I want to be a girl, your girl. I want to be a girl for you.”

I knew it was wrong. I was nine years older than her, but I felt like everything over the last nine years that had happened had always been leading up to this. I had never allowed myself to think about Bobby like this, but that didn’t mean the thoughts weren’t there. I was in love with her and that was why I had forced myself to see her as a guy. Looking at her after everything that had happened I couldn’t see how I had ever seen her as anything other than a beautiful woman.

I leaned in and kissed her. She pulled me in tighter to her and I could feel her breast rubbing against my chest. I laughed at myself for never noticing her breasts before.

We kissed passionately for about five minutes. Our tongues danced as if they had been doing this for centuries. She pulled away from me and smiled. “I’ve been wanting to do that for so long.”

I kissed her on the forehead. I had my hands wrapped around her waist. I could feel how hard my cock was and I tried to keep her at a distance so that she couldn’t feel it too, but she noticed it despite my efforts.

“Make love to me Jon.”

I looked at her. “What?”

“I want you to make love to me. Right here in the garage. It only seems right to do it here. I want you to be the first and last man I‘ll ever be with.”

“Bobby, are you sure? I mean you are only eighteen. You can‘t be sure that I‘m what you want. There are so many other guys out there that would love….”

“Love what Jon? They would love the change me, to turn me into some kind of pink loving, skirt wearing prissy little bitch. No, there are no other guys out there Jon. You understand me and you have excepted me over the years. Yes Jon, I‘m more sure about this than anything. I have been able to trust you more than anyone else in my life. You have been my best friend. You have been the brother I never had and now I want the part of you I‘ve never had. I use to watch you with your girlfriends and I always wondered why I hated them so bad. I know now that it was because I was in love with you. I have been for a long time now.”

There was no argument I could put up. I didn’t want to either. I knew I was in love with her and I knew it would have broken my heart to have seen her with some other guy. I cupped my hands under her nice and firm ass and picked her up.

I walked over to the hood of my car and sat her down on it. I walked over and hit the switch on the garage door to close it. Before it was completely closed I already had her shorts off of her and was on my knees in front of her beautiful pussy. Oh and her panties, they were cotton bikini briefs, black and sexy, but completely in my way at the moment.

I took my hand and started rubbing her bald little pussy. To my surprise it was already wet. I took my thumb and ran it in a circular motion over her clit. Then I spread her lips apart and took my tongue and started licking her already swollen clit. She lay back on the hood of the car and moaned. I took a finger and carefully slid it into her opening. She involuntarily clenched her muscles around my finger. She was tight, tighter than any of the women I had ever been with. I knew she was a virgin, and I felt a little shame at what I was doing, but as I heard her moan and felt her hands in my hair all of my guilt turned into wanting to please her.

I couldn’t believe this was happening. I was here with a girl that was 9 years younger than me that until this day I had always seen as just one of the guys, but now I had my tongue buried deep into her “not so guy” hole. She was moaning and pulling my hair to pull me deeper into her pussy. I was using my finger to rub her clit as I tongue fucked her.

“OH, JON. THAT FEELS SO GOOD. YOU DO THAT SO MUCH BETTER THAN JANET!!!” She had never sounded so much like a woman or a girl for that matter as she did at that moment. I could feel my cock begging to be let out of his zipper locked cage. I don’t think I had ever been that hard in all my life, especially after getting off earlier in the office. “Oh god Jon, this is great, but I really want you. I want you inside of me. We can play later. I want you to make love to me right now.”

Barely able to contain myself I pulled myself up to a standing position in front of her. “There’s a cot in the back I’ll go get that. I want you to be comfortable and I don’t think you will be on the hood of my car.” I started to walk to the back of the garage.

“NO! I don’t want a cot Jon. I don’t want to lose my virginity on a COT!” She said “cot” with a great deal of disgust. “I want to be on the car. It’s my fantasy of you and I. I have thought about it many times and this is what I want. I’ll be okay.”

She took her shirt and pulled it over her head and scooted back on the hood of my car. I was astonished. None of the girls posing naked on the hoods of various cars on the calendar at work looked even close to as beautiful as Bobby did sitting naked on the hood of my car. “Bobby, you are beautiful.”

I unbuttoned my pants and pulled them off. I pulled my t-shirt off and walked over to my car door and pulled out a blanket that I kept inside. I didn’t want the blanket beneath us. No I wanted to feel that metal on our naked bodies. I got the blanket and folded it up for Bobby to rest her head on. I knew she would never complain, but I wanted her to be as comfortable as possible.

After the blanket was in place up next to the windshield, Bobby rested her head on it. I climbed on top of my car. I lay beside Bobby at first. My cock was still so hard it was hurting, but I didn’t want to rush this. I wanted it all to be perfect. I wanted to fulfill her fantasy.

I could feel her looking at me, at my cock and my chest and my body. She finally met my eyes and smiled. “You have quite an impressive…” She pointed at my cock. “I’ve never seen a man naked in real life, but I’ve seen a few in a magazine my sister has and I think yours is bigger than any of theirs.” She ran her hand down my chest. My skin prickled in goose flesh. “I’m a little nervous and I don’t really know what to do.”

I kissed her lightly on the forehead. “It’s alright. If I do anything that makes you uncomfortable just tell me and I’ll stop.”

“Jon, I could never be uncomfortable around you. That is why I know this is right. Being with you is like being with a different version of myself. You are the “me” that actually has a dick.” She laughed a little. Her smile faded and she looked me in the eyes.

Her eyes were filled with desire and a hint of nervousness. I leaned in and kissed her. She pulled my face in harder and kissed me harder. Then she pulled me on top of her.

My cock was resting between her pussy lips, pointing up to her belly button. I couldn’t help but start thrusting my hips. My cock was rubbing up and down her slit. I could feel her clit rubbing the under side of my cock. It was so hard and I was so turned on I knew if I kept doing this I would cum on her belly.

I shifted to where my chest was still laying over her, but I was on my hip on the hood of the car. It was a little tricky to keep myself like that with the bow of the hood, but I managed. My cock was laying on her hip. I took my hand and ran it down her belly to her pussy as I kissed her.

I took ring and middle finger and struggled to get them inside her tight little hole. I knew that if this was hard to do it would be really hard to get my cock inside her and I knew it would hurt her. I wasn’t large, maybe about 6.5 inches and kind of thick, but nothing fantastic, but her pussy was so tight that even I could hurt her.

She was panting and thrusting her hips to meet my fingers. Her breathing was labored. “Jon, Please!!” she said in a pleading voice. I knew what she wanted. I was just so afraid of hurting her.

I pulled my fingers from her pussy and rolled on top of her. “Am I hurting you with my body weight?” I whispered.

“Jon, just because you see me as a girl now doesn’t mean I’m weak like one. Now just hush and make love to me.”

I sighed. I took my cock and rubbed it up and down her slit. I could feel the combination of my pre-cum and her pussy juices lubricate my cock. I did this for a few minutes and then finally lined my now liberally wet cock up with her tight little hole. “This will probably hurt for a minute. If it’s too bad just tell me and I’ll stop.”

She nodded her response. She looked a little scared. I had never seen that look on her face before. She looked nervous and vulnerable. It turned me on even more.

I pushed the head of my cock into her hole. Her pussy was resistant, but with a light pop, the head of my cock was completely in. I felt her wince under me. I stopped, with just the head of my cock inside her. “Are you alright?” I kissed her forehead.

Again she only nodded her response. Her face was somewhat scrunched with pain, but she pushed her hips forward to urge me on.

I slid a little more of my cock inside of her very slowly. She gripped my shoulders tightly and bit her lower lip. I kept pushing in until I felt something blocking my way. It was her hymen. I knew that this was going to be the real painful part. I was tempted to just pull out of her and stop, but just as the thought crossed my mind she pushed her hips forward with one hard thrust and pushed my cock through her hymen. She took her own virginity, just with my cock.

Her face twisted with pain and she bit her lower lip hard and moaned in pain. She didn’t scream out, but I knew if she wasn’t so suborn she would have.

“Oh God, Bobby. Why did you do that? I could have gone easier than that.”

She was panting with pain. “That is exactly why I did that. You would have drawn it out and went too slow. It’s the band-aid principle. Just do it fast and the pain will pass.” She had a point. It was always better to just rip a band-aid off than it was to slowly pull it off. I couldn’t argue with her reasoning, but this wasn’t a band-aid we were talking about. She smiled through her pain. “I’m okay Jon. The pain is starting to go away now. Just keep going. I’m liking the way you feel inside of me.” She didn’t wait for me to decide to keep going. She started thrusting her hips forward and backwards, causing my cock to slide in and out of her tight little pussy.

I started moving with her. I looked down and mused at the sight of my cock sliding in and out of Bobby’s pussy. There was a tinge of blood on my cock and around her hole, but it wasn’t bad. I was still in disbelief. I couldn’t believe that Bobby was this beautiful and she wanted me. Her pussy was so tight and her breast were so firm I knew I wouldn’t be able to last very long.

I pushed in and out of her, feeling the warm walls of her pussy surrounding my cock. She was thrusting with me and moaning and panting as we made love.

I was going slow and being careful with her. I was kissing her and I slid my cock in and out of her pussy. I could feel her pussy contract every once in a while. I moved around to try to find a spot inside her pussy that would drive her wild and also to try to make myself last a little longer. I had always been told I was good in bed, but I had never really put forth any effort, but at that moment with Bobby I wanted to be the greatest lover in the world.

I pushed down with my body as I pulled back and then pushed back in her pussy with my cock going in at a different angle. This was the spot. She moaned loudly. “OH YES JON! Yes baby, right there. Keep going baby. I’m about to cum.”

I was excited that I had found her spot, but the problem was that at this angle it felt amazing to me too. I was hoping and praying I would last until she came. I tried to slow down so that I would last a little longer, but it did me no good, because she started moving faster. Thrusting her hips forward, forcing my cock to slide in and out of her.

I couldn’t hold it off any longer. I was disappointed, because I knew I was going to cum before her, but there was no fighting it any longer. I had to let it lose. “Oh baby, I’m cumming. I’m…ohhh” I shot my first string of cum into her just as she pushed her hips forward, in doing so pushing my cock deep inside of her. She felt my cock throb with it’s release. This sent her over the edge.

“OH GOD! OH GOD!” Her pussy started contracting around my cock. I shot my second and third string of cum into her as her pussy milked my cock. Both of our bodies were quivering as I shot string after sting of cum deep into her contracting pussy. She was shaking and bucking so hard beneath me it almost caused me to pull out of her completely. I shoved my cock in hard and it was almost like it caused her orgasm to start all over again.

“OH JON, YES… OHHHHH… YEEEESSS!!” She panted and screamed. Her pussy was still contracting hard around my now softening cock. She wasn’t done though. She kept pushing her hips up to mine. Her legs were wrapped tightly around mine, holding me into her. She kissed my neck and bit my chest and ran her fingers in my hair.

I was amazed when I felt my cock getting hard again. NEVER in all the times I had had sex had this ever happened. I had always had to take at least an hour to recover before my cock would do anything but stare at the floor, but with Bobby he was ready to go back into battle.

“I want it hard this time Jon. I’m not a virgin anymore and I want you to fuck me this time.” She panted in my ear, still bucking her hips up to mine.

My cock grew completely hard. Almost as hard as it did when we first started. I rolled over on my back, pulling Bobby on top of me as I went. She smiled down at me.

She started slow at first, but then quickly picked up the pace. She was bouncing up and down on my cock and rolling her hips as she did so. I had never felt anything so wonderful in all my life. I looked up at her with her beautiful breast bouncing as she rose and fell on my cock. I couldn’t stand it, I had to kiss her. I had to have her wrapped in my arms.

I grabbed her shoulders and pulled her down to me and kissed her, while I thrust my hips up and down to keep fucking her beautiful pussy. It must have put her at just the right angle, because on the fifth thrust into her she bit down on my lip and her pussy started contracting again.

I pulled her tighter to my mouth, for one because I wanted to be kissing her as she came and for two to keep her from biting my lip off. I could feel her pussy juices flowing down my cock and onto my balls. I had never seen anyone cum that much. It was like it was free flowing from her pussy.

Her contractions started slowing down. She was moving slowly back and forth on my cock now. I hugged her body tight against mine. I hadn’t came that time, but I didn’t mind. She had and that was all I was worried about, but apparently that wasn’t good enough for her. She wouldn’t allow me to not cum too.

“I want you to fuck me from behind now. I want you to go as fast and hard as you want.” Her voice was heavy with tiredness, but she was a trooper and I knew it would do me no good to argue with her about it.

She pulled herself off of my raging hard cock and urged me to scoot over. She got on her hands and knees with her face facing the windshield. I could see her reflection in the windshield and she smiled at me through it.

I positioned myself behind her and slid my cock deep inside her. I started pumping in and out of her, holding her hips and pulling them back as I thrust forward. It felt wonderful. I could see her face in the windshield as well as her breasts as the bounced and flowed back and forth as I fucked her from behind. She was smiling and moaning with pleasure. She met my eyes in the windshield and winked at me with lust and love written all over her face.

I couldn’t hold on anymore. I hadn’t even felt the urge to cum until she winked at me. I unloaded my cum deep inside her pussy. With each thrust I shot a string. I felt her pussy start to contract around my cock again. She pushed herself back on my cock hard, almost causing me to sit. This made my orgasm ten times stronger than it had been.

“OH FUCK, BOBBY… OH MY GOD…” I had never came that hard in my life. She was pushing herself back on my cock as I shot more and more cum deep inside of her. Her pussy was convulsing. Her juices mixed with my cum were dripping from her as I fucked her.

Finally spent, we both lay down on the hood of my car. There were spots all over it, but I didn’t mind.

She sat back, resting herself against the windshield. I joined her by her side. She took the blanket and covered us up with it and lay her head on my shoulder. We fell asleep like that.

The next morning I woke up to voices calling mine and Bobby’s names.

“BOBBYLYNN? Where are you girl?” It was Bobby’s mother.

I shook Bobby to wake her up. Then I heard my brother. “I’m sure they just went on in to the shop. I’ll check the garage to see if Jon’s car is here.”

“Fuck, Bobby, wake up. Your mom is looking for you.”

She woke and jerked up when she heard her mother call her name again. “Oh shit, where are our clothes?”

“Well if I can find the right key to open the garage.” My brother said. I didn’t know what to do. Then he said. “Shit, I have the automatic opener. I’ll just open the big door.”

I heard the door start to screech open. There was nothing I could do. My clothes were M.I.A. as well as Bobby’s. We were caught. There was no getting out of this. Bobby must have realized this too. In true Bobby fashion, instead of panicking and freaking out, she wrapped her arms around me and kissed me as the door came completely open.

The only thing covering our naked bodies from my brother’s view and from Bobby’s mothers was the blanket. Even though I was kissing Bobby I still clearly heard the gasp from her mother and I heard my brother say “Oooh Shit!” in a dreadful voice.


I broke the kiss and turned my head, fully prepared to start spouting explanations that would only make me look more guilty, but it wasn’t necessary. Bobby’s mother was not angry, she wasn’t upset or even sad looking. She did looked shocked, but as I looked at her a smile spread across her face.

“OH BOBBYLYNN, I’m so happy!” She said.

You could have heard a pin drop. Bobby, me and my brother all had identical looks of shock on our face.

Bobby’s mother looked at all of us and gave a light giggle. “I’m sorry. I know I should probably be angry about this, but Bobby is 18 now and honestly I’m so glad to see her here with a man. I was so afraid that she was going to be a lesbian. I lost so many hours of sleep wondering how I was going to tell the people at church.” She paused for a minute and then looked me in the eyes. “I don’t approve of you two sleeping together without being married, but I guess that is a minor thing in comparison. Jon, I kind of always hoped you would bring her around. I mean I hated that you supported her obsession with cars, but I kind of always noticed how she would act around you and I always wondered if she was attracted to you. I knew if you could see past her boyish clothes and her short hair you would see the beautiful girl I had. I just didn’t have much hope of that ever happening. I’m glad it did though. I really hope this wasn’t some kind of fling?” she said the last as a question.

“Oh no ma’am.” I stuttered. “I actually care a great deal for Bobby and I know it’s a little late to say this now, but I’m glad I have your blessing.”

Bobby still had an astonished look on her face.

Her mother smiled at her. “Oh Bobbylynn, don’t look so shocked. I was young once. I already had a child when I was your age. How can I be upset with you over this?”

Bobby smiled a nervous smile. “Thanks Mom….. I guess.”

Her mother smiled at her. “Now, lets all go over to my house and I’ll fix breakfast for everyone.”

“Hell yeah.” Todd said. “I’m always up for some of your pancakes.”

They both looked at me and Bobby expectantly. “You guys coming?” her mother asked.

“I’m willing to bet they did plenty of that last night.” My brother laughed.

Bobby’s mom elbowed him in the ribs. “Let’s not be nasty now.” Then she looked at us again and a look of understanding came over her face. “OH.. I guess I need to let you guys get dressed then. Todd, shut the garage door. We don’t need to be putting on a show for the neighborhood.”

The garage door slowly shut. Bobby and I looked at each other and burst out laughing. “Oh My God. I can’t believe that just happened.” she said between giggles.

I looked at her. “No shit. Can you believe she was happy about it?”

“I guess I better never tell her how this came about.” Bobby smiled at me. “So it will take her a few minutes to get the pancakes made.” She said with a wink.

“I’ve created a monster.” I said as I leaned in and kissed her.

We made love once again on the hood of my car, before going in to breakfast.

After that day, Bobby still dressed like a boy. She still kept her hair cut short and toped it with a baseball cap and she still worked on cars and played basketball with the guys. To all of them she was till just one of the guys. They all knew that she and I were together, but they never seen the feminine side of her that I got to see every night.

We got married after a few years of lust filled dating and now we have three boys of our own. One of which loves to play with baby dolls and only has female friends in his second grade class. I’d be lying if I said I wasn’t worried.

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