Thank You, Heather Ch. 01

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Brad recovers from a breakup with a Craigslist hook up.
4.1k words
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Part 1 of the 2 part series

Updated 10/21/2022
Created 12/28/2014
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The last thing I expected when I got out of the shower that morning was to see my girlfriend Shelley lying naked on the bed.

"Come here," she said with a grin.

It had been about two months since we'd even so much as touched each other, but I wasn't going to bring that up now. She was lying on the bed, completely naked, and although I didn't really have time, I would take the risk of being late for work.

I was hard by the time I crossed the room, and I knelt between her thighs and leaned over her as she immediately grabbed my cock and rubbed it on her pussy to get me lubed for her. She grabbed my ass and pulled me inside her. She made it perfectly clear that this would be a quickie, and that she wanted it hard. Naturally, I obliged. I was still somewhat in shock when she tossed her head back and moaned my name.

"Oh, Brad, fuck me harder."

I'm never a minute man in the morning, but two months without a woman's touch makes a man do funny things. She felt good. She felt tight and warm. She felt like my wonderful Shelley used to feel three years ago. In just a minute or two I was ready to cum, and I pulled out and covered her belly with my seed, as was our custom.

As I cleaned myself up, I apologized that it was so short. I quickly got myself dressed and ready for work - it looked like I wouldn't be late. I continued with my apologies, intermingled with exasperated thank yous while I waited for my coffee.

"I love you, Shelley," I said as I kissed her goodbye.

When I came home from work that day, there was a note on the kitchen counter.

"Brad, thank you for the last three years, but I'm sure you agree with me that it's time to move on. I'm moving back to my parents place in Scarborough for now, and all of my stuff is already there. I'm sorry to do this in such a fashion, but it's the best I can manage.

Sincerely, Shelley"

I became broken. By rights I should have seen it coming, but I was so hopeful that we'd work it out that I had become wilfully blind. After three and a half years together, the spark was gone, the sex was boring and infrequent, and we were spending most of our evenings and weekends apart. I don't think she cheated on me, but I had guessed that she was maybe having feelings for other men. I never got to that point myself, mostly because I'm too stubborn to admit that I was going to lose her.

The date she moved out was March 28th. I didn't leave the house for anything but work and basic groceries until the end of April. I told my friends I was too busy with work to do anything, or I was sick (which was half true, although it was likely just plain laziness and lack of stimulation that caused it), or I had family over. Always an excuse to get them off my case for a while.

After spending a month essentially all by myself, I had exhausted everything of interest on Netflix. Even the stuff not of interest on Netflix. It finally occurred to me that Shelley was gone for good, and that I had to move on. Looking around my condo apartment, it was pretty gross. I had slept mostly on the couch in front of the TV, I hadn't recycled, done dishes, or even really opened the curtains. I spent an entire day cleaning and basking in the limited natural light that my fourth floor unit allowed. I swore I wouldn't lie down on the couch, get fast food takeout, or turn on the TV. It was time to get back to the man I was before I met Shelley in October 2010.

I had been about to turn 25 when I got my first job as a Customer Care Representative for the Ministry of Health in Toronto. That was what a History degree from the University of Toronto got me. Sure, I could have become a teacher or used the degree as a platform in to law, but I was tired of education. I wanted to earn money, not increase my student loans. The student life was no longer for me, and I felt like I was ready for predictability and responsibility. I applied for as many government jobs as I could, and this was where I ended up. It was ok money to start, and after three years I had moved up four pay grades and saved enough to buy a 1000 square foot condo only 20 minutes from work. I was happy to not be wasting money on rent, but it wasn't fancy.

The fourth floor meant I had a view of nothing, but it was mine. The bonus, though, was my real estate agent, Shelley McFarland. She was the cousin of a friend of a friend, and had been a realtor for only three weeks. I knew little about the real estate market, but I figured a brand new agent would work hard for me, and definitely could use the money. I have no interest in making the rich agents even richer. She showed me four or five places in two days, and not only did I find the right condo, I felt like I found the right woman. The day that the deal went firm was our first date: she took me out for drinks to celebrate. I ended up at her place that night and probably lost ten pounds over the next 24 hours just from having sex. Six months later she moved in with me.

We never had a crazy kinky sex life, but the first year we fucked at least three times a week. It was usually pretty vanilla, unless she got drunk. She could suck dick for an hour if she was drunk enough, but never while sober, and she never swallowed. She usually liked missionary only, and rarely anything rougher than a gentle nipple pinch. One day I bought her a little vibrator bullet and got her to use it while she was completely shitfaced drunk. She used it on her clit while I fucked her - it was probably the kinkiest thing we ever did. She was so drunk though that she barely remembered, and was too embarrassed to ever do it again.

Eventually, her schedule as a real estate agent versus my schedule as a day jobber drove us apart. Or maybe we just weren't right for each other, and the mismatched scheduled magnified the cracks in our relationship. I always felt she spent too much time on her job and not with me, and she felt I was demanding and selfish. I wanted more kink in our sexual relationship, she told me I was perverted. It went on from there, until she finally decided she needed to move on.

My heartbreak was more for the loss of a lover and companion than it was about Shelley McFarland herself. But, after a month getting over it, it was time to move on. My apartment was cleaned, my mental cobwebs had been cleared, and holy fuck was I horny. As I thought about the immediate future, I realized that I really didn't want a girlfriend again right away. I needed some time to myself as a functioning social person, but I could really use a good fuck. I never liked the bar scene or trying to pick up random chicks, so I thought I'd try the Internet route. It had worked a few times in university, producing a few good memories and one decent girlfriend, but things had changed a lot since then. I looked around a few dating sites and found they weren't great for random hookups (too many guys like me trying to do the same thing), and Tinder seemed too ... well, I felt too old or too unhip for Tinder. Without wanting to spend money on a hook up site that was mostly filled with fake profiles, I figured I'd try my luck on a craigslist ad in the 'casual encounters' section. I expected very little from it, but it seemed worth a shot for minimal effort.

"Single professional male in downtown Toronto is looking for an attractive 25 - 35 year old female to meet this weekend for a drink and ... who knows? Prefer something no strings attached, but not much in the way of rules beyond that. I'm 28, professional, 5'10", brown hair, clean shaven, fit(ish) and ... well ... it's been a while. I'm not picky about things like race, body type, etc., other than I'd like to meet someone who is comfortable in their own skin and gainfully employed."

I took a selfie, hoped I didn't look too ridiculous, and posted it. The responses I got were certainly from professional women, but I was confident that I didn't need to pay for sex at this point. I had a few offers from dudes too, but again, not that desperate. Such is Craigslist. But I did get one response that caught my eye.

"Hey, so this is kinda weird as I've never replied to an ad on here, but we might be neighbours. At least I think so. Without revealing too much, I live in a condo on Yonge Street. Do you?"

I was actually pretty doubtful that I'd get a response from a real woman at this point, but this seemed legit. Hopefully it turned out to be a real, honest-to-goodness woman with an actual legitimate vagina who didn't charge by the hour.

"Hey! Yes I do. Are we in the same building? Could you send a picture? Please tell me you aren't looking for a client ... not interested in paying for companionship J"

"Quick response! Awesome. And no, I'm kind of in the same boat you are, just a friendly gal looking to meet someone new without any obligations. We don't live in the same building, but I think you and I must work similar hours, as I sometimes see you going into your building a little after 5. Wow, this sounds totally creepy! Ok, please don't be scared J I'm in the building across the street. I haven't noticed you noticing me (feel free to admit it if you haven't) as I've only been here a few weeks, but my pic is attached. I'm free tonight (Saturday), btw. Hoping to check out the David Watson Trio at the Hatter & Cock Pub. Let me know if you're interested and available?"

When I saw this woman's picture, I would have cancelled an appointment with the Queen to meet up with her. I guessed early 30s, and the most gorgeous eyes I've ever seen. It was a selfie, so I couldn't see much below the shoulders, but she was fucking stunning. I wrote her back right away.

"I'm honestly not sure I've seen you before, but wow! Ok, yes, I am definitely up for a drink tonight. 9 pm?"

We agreed, and I spent the next three hours showering, shaving, making sure everything was just right inside the condo, just in case. I went to the liquor store and stocked up a few long-neglected items: craft beer, wine, and whiskey. Again, just in case!

I'm a punctual fella so I was at the Hatter & Cock right at 9. I was pleased to see she was already sitting at the bar, ordering a drink. Well, 'pleased' is an understatement. She was wearing a pair of simple thigh high black boots, tight black leggings and one of those long sweaters that hang just below the ass. I would normally think this was not a proper substitute for pants, but I'm not a hugely fashionable guy (nice jeans and a plaid collared shirt was my chosen attire for the evening) and she looked incredible, so I got over it. Her top covered her to her neckline, but the sweater was tight enough to show curves, and boy did she have them. She had what I consider the perfect body: big tits, round ass, and not fat. So, 'pleased' is being polite. I was goddamn fucking delighted to have this woman as company for a while.

"Hey, I'm Brad," I said.

"Heather. Nice to meet you," she replied.

We both ordered Mill Street beers while we broke the ice for a while. I told her the aforementioned tale of Shelley (with a little less emphasis on the misery). I found out that she was a clerk at a huge law firm and just moved to Toronto from Sarnia. She was engaged until a couple of years ago when her fiancée decided he preferred the company of men. She tried dating women for a bit (schwing!) but definitely 'still preferred the cock'. I couldn't believe how forward she was, especially on a first 'date'. As we got a couple of beers in and the band started and the bar filled up, we got closer to each other and a little more touchy feely.

"I want to see how well you cleaned up today," she said after a couple of hours. "Take me to your apartment."

I left $50 on the bar and we left quickly. It was only a ten minute walk home, and had a sexually tense conversation about neighbourhood weirdos as we made our way to my place.

As we got in the elevator to head upstairs, she leaned against the wall and pulled me towards her. My tongue immediately was in her mouth, her hands on the back of my head holding me close. It was a short ride to the fourth floor, and as much as I didn't want to stop at that moment, I was eager to get inside my apartment. And Heather. I was still a little scared that something would go wrong (maybe she had a dick, maybe she was a just a cock tease, maybe she's on her period) but I was anxious to see how things could go right.

As soon as we stepped inside I was about to say "Do you want the tour?" but she attacked me. I was ok with that. We were kissing like we'd known each for years and this was a big reunion. It felt familiar, yet the excitement of a new mouth was causing severe discomfort in my jeans. We were still standing in the small foyer in my apartment when she started in unbuckling my belt. This woman meant business! I was already anticipating the freedom from my jeans, and when she got my pants opened my rock hard dick sprang to life, gasping for fresh air. It didn't have fresh air long, as Heather quickly got on her knees and took me in her mouth. There was no licking the shaft, teasing my balls, tonguing the head ... she swallowed most of my seven inches in one go. I gasped. Perhaps too loudly, as she looked up at me with a slightly worried look.

"Show me your bedroom," she said.

I left my pants by my front door. In the 15 seconds it took to get to my bedroom, it occurred to me that I had jerked off once in the last month - I spent 20 minutes watching redhead lesbians on Redtube one night a few days ago as I was beginning to come out of my funk. It was the only time I'd cum since I'd fucked Shelley that fateful day that she left me. This could be a disaster if I wasn't careful.

We tore each other's clothes off as we kissed. I thought I could taste my salty pre-cum on her tongue, something I hadn't experienced in years. Moments later we were lying on the bed, and I had her right nipple between my thumb and forefinger as she stroked me. She made a point of putting me on my back and really started taking her handjob seriously. It's no secret that men don't like handjobs from women as much as any number of other activities: we do it so much better ourselves. But this ... this was art. This was science. This was perfection. She kept it up as she kissed her way down my body: lips, chin, neck, chest, nipple, other nipple ... were those teeth intentional? She made her way back down to my cock again, where she again inhaled me.

We hadn't bothered to turn on the light, but the light that came in from the hallway showed me what a beautiful woman this was. Honestly, a lot of women can look great from this particular angle, but I saw such incredible curves, and perfect 34D (or thereabouts) breasts. They swayed just enough as she bobbed up and down to tell me that these were in peak condition, with just the right amount of sag to be perfectly natural. Her brown eyes were closed, except for brief moments when she looked directly into my own. They were bright, but with a wildness I'd never really seen before. Not a dangerous or unstable wildness, but an 'I can do what I want with you' look that was both enticing and comforting.

I could feel my orgasm coming on quickly, so quickly that there was little I could do to hold it back. She had one hand cupping my balls and gently massaging my prostate, the other was jerking me in sync with her mouth, and I had a handful of her beautiful thick brown hair in my left fist.

"Oh my god I'm gonna cum," I moaned.

Well, that just made her work harder. I could feel the suction on my cockhead, and occasionally her tongue would flick the tip when her mouth went up that high. My hips raised off the bed as I shoved my cock deeper in her mouth. I felt my orgasmic load move quickly from balls, up the shaft and out in to her mouth. Bless her, she was ready and willing. She eagerly swallowed everything I gave her, and it was big load - I'd only cum a handful of times in the last few months. I felt a few drops escape her mouth and run down my cock, but she chased them down and swallowed them too.

"Jesus, Heather. I don't know ...," I started.

"It's ok. I know it's been a while. But now, beautiful Bradley, I want you to return the favour," she said.

She leaned up and kissed me. I could definitely taste myself on her this time, and for some reason it turned me on. Everything about this woman turned me on. I hadn't been with someone so willing and so self-confident since the early years of university, and I don't think I'd been with someone this good-looking before. Not that Shelley wasn't attractive, but Heather definitely a full woman's body. I took it in in full as I eased her down on to her back. There was just enough light coming in from the hall to give me the full picture, but it was still dark enough to set the mood just right.

She wasn't a tall woman, maybe 5'3", so her legs weren't long but they were shapely. Her skin was milky pale and smooth to the touch. And to the taste. I licked all around each of her huge, perfect tits until I got to the middle, spending ample time on each nipple. She cradled my head while I did so, mumbling various words of encouragement as I'd flick her left nipple with my tongue while gently pinching the right. I'd switch, nibble gently on the other for a moment before sucking on it. I held them both in my hands as I traced a saliva path down to her belly button, which I teased with my tongue before kissing it.

My cock was already rock hard again by the time I reached her pussy. She was freshly trimmed, shaved a little in from the bikini line. She kept herself well, and she smelled wonderful. I hadn't had my face this close to a pussy since my first six months with Shelley. I had to restrain myself from diving in. With my hands still on her breasts, I licked her from the bottom of her opening right up to her clit, which I sucked gently between my teeth. I heard her suck in her breath as I brought my hands under her ass and lifted her closer to me. I sucked on her clit and flicked it with my tongue. Every move I made brought an audible reaction.

I pulled my hands out from under her ass and used my left hand thumb and forefinger to expose her hood, and I inserted the middle finger of my right hand in her wet pussy. My god it had been so long since I've done this, but I hopped right back on that bicycle like I'd done it yesterday. Well, I hoped I was doing it right. By Heather's reaction, I was. I explored her insides with my finger as my tongue did gentle laps around her clit. She was thrusting her hips into my face and I pushed back with my mouth. We had a wonderful rhythm going as I started using two fingers inside, curving upwards, aiming for her g spot, feeling her wetness gather in the palm of my hand.

My jaw was getting tired but I wasn't going to finish until she came. I fingered her harder, I worked my tongue harder on her clit. I looked up to see her head was tilted back and she was breathing harder, pushing with her hands against my headboard. She was on the edge. I got on my knees and doubled my efforts, alternating between gentle tonguing and slightly-less-gentle sucking, and my fingers were locked on her g spot.

"Right there," she said, breathlessly, but forcefully.

I was making the final push when her whole body shuddered. She moaned, I think. Maybe it was a grunt? A shout? She made a strange noise, and she grabbed my head and brought me up to her face where she kissed me deeply.

Before I really realized it, she had guided me inside her, with my cock this time, instead of my fingers. She felt amazing. I set a steady pace from the beginning and she matched it, not only with her hips but with sounds. She grunted a cute little grunt with each thrust, and she brought her hips closer to mine just a little. Her legs were wrapped around my waist and her left hand around my neck, holding on, pulling me in. We fucked in a steady rhythm, kissing, tasting each other. I leaned over and took her each of her nipples in my mouth in turn, teasing each my teeth, never changing the pace of our grinding sex organs. She pulled my hair a little if I bit too hard ... not as a warning, but because she liked it. That made me go faster. I pushed myself up so my head was directly above hers and fucked her pussy as I hard I could.

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