Caitlin's Best Friend

A little about me...

My name's Caitlin, I'm 32 years young (ha ha, sorry, lame joke), I've only had two lovers in my life, been with the same man, Brad, since college and happily married for the last 3 years. We have a beautiful house together, both of us have great jobs that pay well, a healthy sex life, and are in love. To everyone on the outside we're the picture of happiness.

For the most part they would be right but there are always cracks, you know? I should explain, my first full intercourse partner showed me the joys of different positions, a more aggressive style and he enjoyed all the tricks I picked up over the years of pleasing men without intercourse. But his heart belonged to another, eventually relegating me to a friend with benefits and eventually I left. My second partner was Brad and he is shockingly good in bed, like me he is more aggressive in the bedroom than anyone would have ever thought, including me. He was the first man I was with for a long period of time and as we learned each other the sex got incredible.

You see I love sex, I really really do, and I'm not a nympho or anything but the feeling of an orgasm that makes my toes go all curly and tingly is heaven. I have a small frame, average sized breasts, a killer ass if I do say so, pale skin and red hair. I dress pretty conservatively, showing my curves but barely any skin, underneath that it's a toolbox really, some days it's thongs, g-strings, lace, mesh, others it's boring old panties and boyshorts. All about my mood. The point is that on the outside most people think I'm prudish, a little plain, my friends know I've got a dirty mind, but even they would still not imagine how much I enjoy sexual acts at home. Dressing up, giving blowjobs, teasing, orgasm games with my vibrator, spankings, I love it all.

That part excites me really, knowing I'm dirtier than people think I am, knowing men find me attractive and innocent while unaware that just last night I wore a schoolgirl costume and swallowed my Brad's load. It's sort of reverse exhibitionism I guess.

However, in the last year or so I started to feel like I wasn't as attractive or sexy anymore, and Brad paid less and less attention to me. Sure he liked getting a blowjob still, he liked having sex, but there wasn't as much passion. We stopped going out and instead stayed in and watched TV, he got kind of lazy about the whole process. We stopped experimenting and trying new things and got more into a rut. He used to send me dirty emails daily and I would send him dirty pictures but that stopped as well.

I took it upon myself to fix this via diet, exercise, and attempts at romance through clothing and toys, but it continued to be stale despite those efforts. The ultimate humiliation came when I had to bargain for a 'date night' and even that fell apart after a few weeks, the woman who used to be able to make men salivate by bending over the pool table in the bar couldn't even get her husband to go to the movies. It was a dilemma for me because I loved him dearly and he loved me, we had built a great life together and honestly I didn't want that to change, nor did I want to hurt his feelings by telling him the truth. That I was stifled, that even though we lived together and slept together, I was so very lonely. Often times I would resort to watching porn and masturbating in bed while he played video games downstairs at night as a way of getting something new.

Up until a few weeks ago I wouldn't have considered that my loneliness and longing would have lead me to do something I never saw myself doing again.

A few weeks ago I took on my 4th sexual partner in life.

Chapter 1: A happy accident

It's important to understand that while Brad knows me better than anyone ever has, especially in the bedroom, and my second partner is a close second, there was another: my best friend, Sean. I had met him almost 7 years ago working a dead end job, he was a few years younger than me but you'd never know it talking to him. Our first meeting was when I having a rough day at work, he showed up at my desk with a kind smile, some words of encouragement and (most importantly) some comforting chocolate. We got lunch later that day and hit it off immediately, we liked the same books, movies, had the same political opinions, and he understood me in a way few people do. I felt instantly at ease with him. Soon we exchanged emails and phone numbers, we started hanging out outside of work. Slowly he became my most trusted friend, I could tell him anything and no matter how crazy or intimate he would listen and treat it with respect. For a while I was worried he was after something more than friendship as he was an attractive man, tall, dark haired, confident and carried himself with attitude and a kindness that was second to none, but he never made advances of any kind.

He helped me get through my wedding, when my car broke down he was there to help, when my family had trouble he lent a hand, when I changed jobs he encouraged me. It was wonderful really. We talked about relationships, fears, likes, and sex...my god did we talk about sex. For as adventurous and creative as I was, he had me beat 10 times over. I adored that I could talk to him about all of it and he never took as more than just conversation. Since my life had gotten staler at home I had come to depend more and more on him, and to my shame I had started to take advantage of his kindness and willingness to talk. I would occasionally send him photos of sexier clothing to look at just to hear him describe how beautiful I would look in them. I would ask him about his sexual exploits with whatever woman he was currently seeing. I would steer the conversation to a sexual area and listen to him discuss it. It was wrong and I knew it but the way he talked about it, and me, stirred something in me...my chest would pound as I read it over, I would feel a throbbing between my legs, and maybe occasionally I would save those emails and read them over again later while my hand drifted down...I found that after reading them I would be crawling up the wall when Brad came to bed.

A few weeks ago I had ordered a couple of very skimpy bikinis and finally the package tracking confirmed they were waiting for me when at home. I left work early to go throw one on, then wait to great Brad at the door in it and see where that went. Getting home I opened the box and it was scandalous, the bottoms rode my hips perfectly and hugged the curve of my ass while the top barely covered my nipples. I did my hair up, got on a pair of 6 inch heels and waited to hear the key in the lock. At around 4 my phone rang with Brad's tone, I quickly ran to get it and just about tripped in my heels.

"Hello honey, are you on your way home?"

"Sorry Caitlin...I'm going to have to work late tonight, don't wait up for me okay?"

"Are you sure? I got something kinda special cooked up tonight."

"I'm really sorry, but I just can't."

"What if I told you I was sitting here in a skimpy bikini waiting for you to get home?"

"I would feel even worse about having to work late, but I would know my Caitlin would wear it again for me tomorrow" he laughed

*sigh* "Okay, well, I'll leave you something in the fridge for dinner..."

"Thanks honey, you're the best. Love you"

"Love you too, dear"

Hanging up the phone I couldn't have felt more deflated by the whole situation. I took off the heels and slinked upstairs to shower off my makeup and get changed into something comfy. As I walked past the mirror I looked at my naked body, damnit I was hot and he should want this. I threw on my bathrobe and fired up my laptop while I dried my hair "hmm...maybe some Queen to ease my pain", as I went to hit play a chat window popped up from Sean.

"Hey darlin, you ran off in a hurry, didn't get to say goodbye"

I smiled, just what I needed, quickly typing back "I had a plan for tonight but it kinda blew up in my face"

"Sorry to hear that"

"Not your fault, don't worry"

"Anything I can do to help?" That question stuck out to me for some reason, I felt that stirring downstairs again. I couldn't do what I was thinking though, even if I was mad at Brad...then again Sean did say anything.

I bit my lip and typed back "Nah not really, can I get your advice on something else though?"

"Sure"

I sent him links to pictures of the three bikinis I had bought "What do you think of these?" Setting the laptop down to my side as I untied the bathrobe and let it slip down, as his words came back my hand slide down my stomach, my index finger finding its way to between my already wet lips. My other hand moved to my nipple and tweaked it a bit.

"The white one would sit on your hips just about perfect, side tie as well which is always sexy. I think the small of your back and how it curves into your butt is incredible and I think that would show that curve off very well"

I bit my lip and let out a moan as I slide a second finger inside myself, my god what was I doing? Cyber sexing my best friend in my bed without him knowing? My body was on fire though, my muscles twitching and lips quivering as the first orgasm hit me, my body overpowering my sensibilities, my free hand reaching into my bedside table to pull out my clit stimulator. My leg lifted up to give my hands better access, yelling 'fuck' as the buzzing plastic touched my hot swollen clit. I rocked my hips into it, toes curling as another orgasm built, his words running across the screen still.

I panted hard and dropped the stimulator, I didn't need it with him. My body curling and uncurling like a spring, legs pushing the sheets around, this one was going to be big.

"You still there?"

Oh no, he had to keep talking me through this. I reach a hand out and quickly typed "yes". Then went back, three fingers now, my free hand mauling my nipple. I rolled to my back and arched up, my hips lifting my soaking wet pussy up in desperate search of a cock. Letting out a cry of pure animalistic pleasure as I came, my hips dropped down, sweating, panting, my entire lower body half numb from it all, toes still curled and the tips of my fingers and toes tingling like they were asleep. Fucking hell that was the best orgasm I had had in months.

That's when I looked over and saw Sean's face on my screen, both eyebrows raised and mouth agape. It was then I realized that instead of hitting 'enter' I had hit the video call button, Sean had watched my entire orgasm happen live, my naked writhing body fully on display for him. Mortified I reached up and slammed the laptop shut.

Oh god what had I done?

Chapter 2: The Question.

It had been an awkward night after that. Sean had tried to txt and call me twice but I didn't answer. I pretended I was asleep when Brad got home, having washed the sheets and put on sweatpants to show there was no interest in sex. Poor Brad thought he was in the dog house for working late. I knew Sean would message me as soon as I got to work and steeled myself to try and explain last night. The message came but later in the day, around lunch.

"We really need to talk about last night Caitlin"

"I'm so sorry...you know things have been tough for me at home lately and it doesn't excuse it but I was feeling so lonely...I just needed someone to say something nice to me"

"It's okay Caitlin, look I'm not gonna tell anyone, you had a moment and I'm not going to make that into anything more than that"

A million pounds off my shoulders as I read this, knowing Sean was good for his word "Thank you Sean, really, I cannot tell you how much I appreciate that"

"Of course...besides, it was a hell of a show"

"Really?" Oh goddamnit, why did I type that back?

"I mean, come on, you're incredibly attractive and that was one of the most beautiful things I've ever seen"

Control yourself girl, you cannot let this go any further

"Well thanks, again I appreciate it, but let's not talk about it anymore okay?"

"Sure sure, I don't want you to feel uncomfortable. But it felt like you were pretty comfortable last night you know? Sure you don't want me to do that for you again?"

My jaw dropped, my legs quivered a bit and I felt that stir...gotta fight it though.

"Quite sure...thanks"

"So if I told that you that right now I was thinking about you at your desk in one of your dresses with my underneath it, you wouldn't want to hear where I went with that?"

Fuck fuck fuck fuck, I was even wearing a dress that day. My lower body was begging to know, my brain was screaming to tell him absolutely not...

"Yes..." Fingers? No why do you betray me so! Oh hell, what's the harm I guess, as long as it stays online only.

"Thought so. I would spread your legs, then take your foot in my hand as I kissed it, kissing a trail up your smooth sexy toned legs. When I got to your knee I would switch to my tongue and drag across your inner thigh"

I was soaking wet already, my clit screaming to be touched, lips aching, my god he was making me so horny and there wasn't anything I could do about it at my desk, this was torture.

"I would then run my hands up your legs, gripping your thighs and being sure to hold a thumb on each inner thigh, rubbing it as I slid you toward the edge of your chair, your ass just barely touching it"

My body slid forward in the chair to the position he spoke of, my legs spread out a little.

"Reaching forward with my teeth I would grip the top of your thong and slide it down your legs"

I was wearing boyshorts today but whatever, my hands were white knuckle on the table either way.

"Going back up as I breathed hot air on your wet lips, I would tell you to spread yourself open and show me how wet you were. My tongue would run ever so delicately up around your lips then, stopping just below your clit. Sliding around it and then sucking it hard, flicking it back and forth. Your legs would hook over my shoulders and my hands would cup your ass, pulling you to my face as I moved down and thrust my tongue into your hot soaking pussy"

I swore I could feel it happen, and I let out a small moan at my desk, just about falling off my chair. I could tell my panties were soaked.

"Swirling around, pushing up and down, left and right, bringing you right to the edge of cumming. Then I would stop, lift my head up and ask you if you wanted more or not"

I came down off my high a little, calming and looking at the screen. My brain won this time and I typed out 'no' immediately, but before I could hit enter someone came to cube to ask me a question. I was flush, sweating, panting a little even, quickly I got my composure back and went to help them. An hour later I came back to my desk to find Sean had signed out and gone home without receiving my 'no' message. Knowing I had to get somewhere private to talk to him I packed up and went home for the day, Brad wouldn't be home for a few hours, I'd call Sean and explain that this had to stop right away.

Arriving home I quickly changed out of my soaked panties and dress and into the least sexy thing I had in the hopes that it would help me to break this off before it went further. Getting my laptop out to review his messages quick and find the right way to answer him. As I did an email came in from Sean with the subject line "For you", I sat and looked at it for a few minutes and finally clicked 'open' against all my better judgment.

I began to read 'Coming up the stairs to your room after a long day of work to find you laying on your bed in a tank top and sweatpants. I climb onto the bed behind you, running my hand over your shoulder and kissing it, my other hand running up and down your back. I lay next to you, look into your eyes and tell you how beautiful you are, how sexy you are and how much I want you right now. My hand slides down the back of your pants and cups your ass hard as I lean in and kiss you. You hand reaches down my pants and grabs my shaft, gripping it hard as well. I swat your hand away, telling you it's not time yet, making you wait for it. I flip you over and push my index and ring finger up your tight little pussy, grinding up and rubbing you in that special place that takes your breath away. My mouth wraps around your hard nipples as they poke through your shirt. I pump your pussy as hard as I can, your hips fucking my fingers, listening to your scream as you cum, fingering you through the orgasm. As you lay there I strip my pants and slide up, putting my cock to your hungry mouth. You gobble it down like a lollipop, licking it, stroking it, pumping it, you want my cum so badly. But you can't have it, not yet.

I pull out of your mouth and kiss you, tasting my precum in your mouth as my hands once again knead your ass cheeks. I grab your hair and pull your back, getting off the bed and leading you to the window, pushing you chest first against it as I drop your sweatpants and pull your shirt off. You stand stark naked in the window for the world to see, bent over with your ass in the air. I run my hands up your thighs, teasing your clit, kissing and biting your ass. Now standing and letting my cockhead just rub against your warm wet welcoming swollen horny lips. You beg me to fuck you and I spank you lightly at first but then harder, you beg more. I put my hands on your hips and thrust inside you, my swollen rock hard shaft parting your lips open and filling you up with as much as you can take. I slam fuck you, the only sound our animal like grunts and groans and the noise of our flesh slapping against each other. My cock rubs your g-spot to perfection and you orgasm hard multiple times, barely able to stand as you feel my shaft swell and pump you full of hot cum. I rip my cock from your body, giving your ass one final smack as I do so. The window covered in your sweat, unsure if any of your neighbors saw you bent over taking it like that, panting as you collapse down to your floor completely pleased.

Finished reading and cumming? Good. Now I have one question for you Caitlin: do you want me to fuck you? Think about it and let me know'

I finished reading and looked back to find myself on my knees with my pants around my ankles, panties dropped and two fingers inside myself. I hadn't even noticed it happen, but the bed had a noticeable wet spot below me, I must have orgasmed multiple times. My god it was perfect, a little rough, a little exhibitionist, but over too quick.

No no, I wanted more, so much more from Sean, but I couldn't could I? It would be cheating, but cheating with the perfect man to cheat with, someone who would keep it safe, who no one would bat an eye at coming over all the time.

As I cleaned myself up, washed the sheets again, made dinner, ate dinner, talked with Brad, watched tv, and tried to sleep, all I could think about was the question.

Did I want him to fuck me for real?

*look out for Part 2!*