Peeling Back the Layers

This is a stand alone story I have been playing with over the last while and decided to give it a title and post it. For those who have read my limited work, you know I like a storyline that pushes my characters through many emotions. This one is about love and living with our choices.

Sex is apart of all my stories but it's not the driving component, so if you're looking for nonstop sex (which is totally cool), this may not be a story for you. For those who choose to continue, I hope you enjoy!

C_T

Peeling Back The Layers

"Dude, all I'm sayin is you must be some master in the sheets!"

"It's not the size of the wand buddy... it's the magic it wields!" I retorted to my shower buddy.

Actually, Mike has been my best friend since the 8^th grade, and we've been like brothers ever since. I mean that in the metaphorical sense, since Mike's black and I'm white. We grew up together getting into all kinds of trouble with our parents, teachers and of course the girls. We ended up playing football together and apparently, we were quite good, as we're both playing in college now on a full ride.

"You really need to get over your BBC personality dude! Life ain't like porn bud. There ain't no love in those videos you watch." I had noticed some small changes in Mike the last year, poking fun at my dick, questioning how I can keep a girl like Jenny. I get that it's all in fun, but he was never like that before. It doesn't help that he was blessed considerably in the dick department and although I've never seen it erect, I have no doubt he's quite big... definitely bigger than me, but I was comfortable with my solid 5 inches and so was my girl.

"You ain't wrong Billy boy, but right now, here in college, I got a lineup of white chicks dying for a piece of this!" Mike accented the comment by grabbing his big dick.

"I'm happy for you Mike, but none of that would matter if you found your soulmate. Just promise me you'll wrap your dick! I don't want my best receiver to go down with some STD or end up in court with paternity charges." I meant it to sound like a joke, but there was a part of me that did worry about him. You see, Mike was there for me when I lost both my parents in a plane crash my senior year in high school. It was truly a dark time for me as I was an only child, and my closest living relative was somewhere in Canada. Being 18, at the time, and the full beneficiary of my parents estate, I was forced to grow up very quickly. Money wasn't a concern as my parents were very well off and between the assets, investments, and life insurance, I was an instant muti-millionaire. Don't get me wrong... I'd trade it all back in second to have my parents in my life.

***

Mike was a huge factor in helping me focus and move on, but my true rock was my girlfriend, Jenny. Jenny and I dated since our first year in high school and she is my everything! Many a night I asked myself how I got so lucky and after more than 6 years, I've learned to accept my fortune when it comes to her. She is like my inner voice and knows what to say and when to say it. She gives me love and compassion when I need it, but also knows when to give me a kick in the ass when I started to become self absorbed. You see, Jenny knows pain and suffering too. Her father OD'd just as she hit 15, leaving her mother with mounds of debt and a mortgage she couldn't afford as a bar waitress. Jenny and her mom have moved many times and are currently living in a trailer park. It's not the run-down version of the movie 8 mile, but it's a trailer... in a park.

Despite this set back, Jenny persevered and for what ever reason she found me, and I was never letting her go. By the way...did I mention that Jenny is an absolute bombshell? I mean a true 11 out of 10! Petite at 5'4", long blonde hair that is forever in a pony unless she's dressed up. Her body is so tight and likely has less than 2% fat on her body which is crazy since the closest thing she does to working out is cheerleading and her diet is anything but monitored. She likes her pizza and beer like the rest of us! Jenny's tits are just right for her body, not too big, not too small, and perky as hell. Her face is flawless with big blue eyes and full raspberry-colored lips... she's gorgeous! Despite all these wonderful traits my favorite part of her body is her ass. I know, I know, that seems pretty shallow, but seriously it's perfect! Small, tight, round... she can make a burlap sack look hot, trust me! Jenny was my first and my only. I'm quite sure that I was her first too, but I never felt like it was ever important to ask. We are so in sync it drives our friends around us crazy.

When I was offered a full ride to play football at a NCAA college, it was the first time I ever saw concern in my girls eyes. We both knew her mom could never afford college and even though she was smart, she wasn't smart enough to even get a partial scholarship. The Christmas before our graduation I surprised Jenny and her mother with a rather large gift. My father had numerous rental properties and one of them was a small bungalow in a nice neighborhood close to schools and shopping. It was all paid for and instead of selling it off, I gave it to them. Her mother initially refused it but after I explained my rational, she began to warm up to it. I know they paid rent on their trailer plus grounds maintenance, and utility bills, so I broke down the taxes and the history of the annual utilities of the house and showed her she would be saving $300 a month, plus the satellite TV and internet was already part of my group plan and therefore would cost them nothing.

By the end of the night her mother had finally relented, and we planned for a moving date at the end of January. To say that Jenny was excited would be a gross understatement. She clung to me all night, kissing and cuddling (her mom was there) and I felt the best I ever had since my parents passed. Doing good for others was euphoric in some ways. That night when Jenny came back to my place with me, we celebrated... vigorously! We fucked in every room of my 2000 square foot inheritance and ended up in the living room cuddled under a blanket together.

"I can't ever thank you enough for what you did for my mom and me Billy. I hope you know I never in a million years would have ever expected you to do something like that." Jenny was staring at me with her big blue eyes.

"I know how hard your mom works Jenny and in so many ways, she feels like my mom too. I love you both and there was something I could do to help, and I did it, that's all."

Truth was, there was something else I could do, and I was about to drop that on her too.

"Which reminds me, we should talk about college."

Jenny groaned. "Please don't bring that up now, I don't think my heart could take it."

It was a difficult discussion for sure. While my going away was a great opportunity for me, Jenny had resolved herself that she would have to hang back here, pick up some lousy job, and wait for me.

"I was gong to wait till new years eve, but I don't think I can." I started.

Jenny crooked her head back to look at my face again.

"With the help of your favorite teacher, we got you accepted into an arts and administration program at the same college I'm going to!"

Jenny's smile was brief as she didn't understand what good was that if she had no money. "That's sweet Billy but you know I can't afford to go."

"About that." I began. "It turns out that being an academic booster for an individuals' education can be a sizeable write off." She still had a blank look on her beautiful face. "Jenny... I'm going to pay for you to go to college with me. Tuition, accommodation, the whole gambit. We won't be able to live together as it would void an aspect of my scholarship, but I was able to get you into a shared apartment not far from where I'll be.

Her face was running through a series of emotions, and I was waiting for the dam to burst. Was she happy? Was she mad? I honestly couldn't tell.

"I can't believe it! Billy my love you are the greatest boyfriend, no, no wait... greatest human being ever!"

After some tears and a lot of hugs, Jenny thanked me with the longest, best blowjob of my entire existence!

***

So, the three of us went off to college, Mike and I on football scholarships, with my girl at my side, looking to make a future for ourselves. The first year and a half was awesome. Mike and I were already starters on the team and Jenny had made lots of friends and was doing well in her program. Jenny's roommate, Ashley, was also a new student and the two became quick friends often doing all the girly things girls do together.

Ashley was pretty, in her own kind of way. She was bit taller than Jenny, but as far as her figure went it was a little difficult to tell. She had a real goth theme to her attire, lots of black, long loose shirts, jet black shoulder length straight hair... at first you wouldn't see it but as I got to know her, she was actually quite pretty, once you got past the drab clothes and dark makeup. I kind of got the sense that she was a little sweet on me but there was never anything obvious or awkward.

Lately Jenny and I have been getting quite adventurous in our sexual adventures, well to be honest, it's more Jenny than I. When we first got here, she spent a great deal of time in my room, and we had fucked on or over everything imaginable. We even adventured into the coed shower rooms and fucked behind nothing more than a privacy curtain. Jenny's appetite for sex was as high as mine, which made our compatibility even better!

About 6 months ago, Jenny had brought up the idea of her using a strapon dildo on me. At first, I was shaking my head in a hard no and declaring in the strongest ways possible that I wasn't gay. But not to be deterred she mad a very long and well supported argument based on three main points. 1) She had given me her ass which she stated was the ultimate in trust on her part and even though she had her misgivings in the past she was glad she did because it was awesome! 2) Why couldn't I allow her the same level of trust. She was just as curious as I was to be the one who did the penetration and how sexy it would be to be at her total mercy. Admittedly she scored a few points with me on that one. 3) How could any part of it be considered gay? We were a couple, a couple in love and shared our deepest and most vulnerable secrets with one another. What we did in our bedroom was for no one else but us. She should've been a lawyer as I could feel my will power begin to crumble and to finish me off, she gave me her sad face pout that was beyond adorable and ALWAYS got me to buy in on whatever she was trying to convince me of.

We spent the evening on my laptop shopping for the necessary equipment (yes, she convinced me). The harness was easy, but I had no idea there was so many dildo options. Short, long, ridiculously long, thin, fat, balls, no balls, black, white, blue... on and on. Some even looked like an alien finger or something, but I think they were more about prostate massage vs ass fucking. Jenny kept going back to a black one that was 9 inches long and fat as hell, but every time she put it in our shopping cart, I deleted it.

"Jenny... let's be fair about this. Yes, you let me fuck your beautiful bottom, but I'm not packing anything like that. You should be using something that's more in comparison to mine."

She pouted at me again. "It's not like I had an option." She stated.

I looked at her face. "What's that supposed to mean? "I asked. It was the first time I ever heard her say anything in reference to the size of my cock.

She quickly dropped the pout and kissed me. "Nothing you goof! I was just being silly. Oooh, how about this one then?" She focused my attention back to the screen with a white 6 inch plain looking dildo, balls too of course.

Giving her the benefit of the doubt, I shrugged my shoulders and agreed. "Are you sure this is what you want to try? You won't look at me any differently if we do this?" Once again, I was searching for a way out.

After adding the appropriate lube to our cart, she hit check out and smiled at me. "Definitely!"

A week later we were in her room on a Friday night and her roommate Ashley had some sort of function, so we were left to ourselves. I had brought a couple of bottles of wine as I figured being a little loose might help me loosen up for our inaugural visit to strapon lane. Jenny was extra affectionate, super giddy, and I could tell she was truly excited by the idea and that helped me relax, as I loved when she was happy. After a few glasses of wine, Jenny became very amorous, and we were making out heavy on the couch. Slowly we were taking turns removing each others' clothes until we were both in nothing but our underwear. Jenny reached down and firmly grabbed my rock-hard cock.

"Oooh, I think my Billy really likes the idea of what we're going to do tonight!" She teased me.

"Anything I do with you gets me hard Jenny! I love you!" I kissed her hard.

She giggled and slowly made her way off the couch but kept her firm grip on my rock-hard cock as she slowly lured me into her bedroom. "Why don't you take your sexy body to bed, and I'll meet you in a minute." She gave me a devilish smile and peeled off to the bathroom.

Not sure how one's supposed to lie on a bed and wait to be fucked, I laid on my back with my head at the headboard and rubbed my hard cock through my underwear. What nerves I had were quickly diffused when Jenny walked into the bedroom wearing nothing but her harness and 6-inch cock around her slim waist and perfect bottom.

"Hey sailor! Looking for a good time?" She teased me as she slowly walked to the bed.

My grip on my cock increased as it was almost painful how hard it was now... she was that fucking sexy! She knelt on the foot of her bed and slowly made her way up until she was straddling my waist. She lowered herself down and kissed me like I was her prey. She lifted her lips from mine and raised her left eyebrow.

"Can I see the goods handsome?"

I just smiled as she lowered herself down my body until she was resting on the top of my thighs. She pulled my underwear down revealing my throbbing cock and she instantly grabbed it and started stroking me. I closed my eyes to the incredible feeling of her hand, and I could feel the touch of the fake cock on my own. I opened my eyes as I watched her bring her fake cock parallel to mine as she stroked them together now.

"Oh baby... I'm bigger and fatter than yours." She cooed and once again she struck a funny chord in me. Sensing my immediate discomfort, she spoke out.

"What's the matter Billy? You, ok?" She didn't seem like she was taunting me so once again I let my pride relax.

"Just nervous Jenny... that's all."

She smiled at my response and slid down further until she pulled my underwear right off and settled between my legs.

"I bet I can do something to help you relax.' He winked and slowly lowered her open mouth to my cock. In one quick gulp she had me down at the balls.

*Could she do that before?*

In no time her mouth had worked me into a frenzy, and I would have sold my soul at this point for an orgasm. Sensing my impending state, she popped her mouth off and sat up. I looked up at her and she made a gesture implying I needed to roll over and I obeyed. The next thing I felt was oil or lube as she began rubbing my ass and worked over the whole thing making sure she made several passes to my tight brown star. Without warning she started to work her finger in and out and I flinched, which got me a slap on the ass.

"Just relax Billy, I won't hurt you. I just know you're going to love this!" She was very convincing.

More time past and she was now actively working two fingers in and out of my ass and I wasn't complaining... in fact I involuntarily moaned a few times which made my girl giggle.

"I think my baby's ready for the real fun." She declared I could feel her position herself with the head of her fake cock at the entrance of my back door. "Just trust me Billy, relax and soon it'll feel great."

She rubbed and circled my anal ring making sure I was slippery and every once and awhile she would stop and press in checking to see if I was ready to give her access. She patiently did this over and over until finally the head slipped past my ring and instantly, I contracted in surprise and pain.

Again, my girl giggled. "Easy baby... easy. That's the worst part. Just breath and let yourself relax." Her soothing words did help me and soon I was starting to relax again.

Like she sensed my comfort level returning, she pushed a little deeper causing me to tighten up again, but the pain wasn't as severe. A few minutes passed and she pushed again... and again... and the next thing I knew I felt her flat stomach pressed against my butt cheeks and her fake balls pressed tight against my own.

"Oh Billy, this is so fucking hot! I got my whole dick inside your ass baby! Tell me you don't love it!" She was directly beside my ear, and I could feel her breasts against my back.

"I love everything you do to me Jenny." I was able to gasp.

"Ok Billy, now it's show time. Bring your hips up for me baby."

With her cock balls deep in my ass, I helped walk her back as I pushed my chest off the bed until I was in the doggy position, except this time I was the bitch. Jenny grabbed my hips and pulled back and inch or two and pushed back in. I could tell she was waiting for my reaction and when she heard me moan, she giggled with approval.

"Oh Billy... tonight we fuck with no inhibitions!" I wasn't sure what that meant but she took the lead and began with some shallow thrusts. I sucked in my breath and groaned, and she picked up on my arousal, thrusting a little harder. What she lacked in technique, for being a girl, she made up for in enthusiasm. I hadn't seen or heard her be this passionate in quite some time and it was infectious. Her ministrations were having a gradual effect on my pleasure and combined with her ooh's and ah's, I was starting to feel quite good!

At one point she started pulling out right to the head of her cock and shoving it back in, right to the balls. I recognized the technique, and I knew it felt good for her when I did that to her. The new depth maneuver was stirring up the weirdest feelings in my groin and at first, I wasn't sure if I might piss the bed, but it clearly was the building of something else, something huge!

Jenny changed her technique just a bit and was now slamming the whole thing balls deep and would pause and grind her cock inside my bowels before pulling out and doing it again... and it felt amazing! Each time she grinded herself deep inside, I could feel the start of an orgasm, but unlike my usual ones, this felt like it was coming from someplace deep... like my soul. Three or four thrusts later, my whole body went into contraction, and I started vibrating from my toes to my nose. Jenny could tell something was going on and stayed hilted to the balls in my ass.

"Billy? You, ok?" Her question wasn't made from concern, it was more curiosity.

"Shhhiiiittt... FFUCK!" Were the only real words I could articulate as a deep groan overtook my voice box.

That's when it happened... I came. I came hard! It took Jenny a few moments to realize but when she did, she was ecstatic.

"OH MY GOD! You're cumming! You're actually cumming from me fucking you! Oh, Billy this is so FUCKING HOT!!"

**

Needless to say, this new dynamic was a hit for Jenny and if I'm being honest, I liked it too. When she found out that my orgasms were more intense from the fucking, she was sure to implement our new practice often. In fact, over the next few months, it was almost down to a regular routine. My fucking her was rarely a thing anymore and when I did it was for only a few minutes before she was topping me to another orgasm. Our sessions, while still hot, were becoming quite predictable... Jenny sucks me for awhile, then she fucks me until I cum. I asked her about getting her off, but she was adamant that getting me off like this was very satisfying for her. It wasn't the type of sexual relationship we grew up together with, but it was making her happy, and I was experiencing some mind-blowing orgasms for sure.