Fuck Buddies

I was more ready to believe the latter, but curiosity started to get the better of me. I mean, I hadn't had sex since I'd been divorced. The closest I came was with Danielle, ironically, and all we did was make out for a while in her car. What if she was right and Wendy wanted to have sex with me? Having her wrap her mouth around my dick sounded pretty appealing, I thought. I felt myself growing hard in my shorts. It had definitely been too long, I thought, pushing myself out of my recliner and off to the bathroom to take care of my hard-on.

Danielle was a big believer in casual sex, before she got into a relationship, at least. She was always telling me that if I wasn't able to find someone to be in a real relationship with, I should at least be looking for someone to fuck. I was hesitant. I wasn't one of those guys who was looking for conquests or notches on their bedposts. I wasn't sappy or overly romantic. I knew myself, and I knew that whoever I ended up having sex with I got emotionally attached to. I mean, they let me fuck them! How could you not have feelings for someone like that?

I started out content to wait until I met the right woman, but I didn't think it would be this hard to find a new relationship. Months turned into years. It had been almost three years since I last had sex now, since my last time with my ex wife. I started jokingly referring to it as my 'second virginity', but the longer it lasted, the less funny it got. And the less funny it got, the more I started thinking that I needed to just get it over with. Waiting for the right situation, the right woman? Fuck it, I needed to get laid.

Did I want it to be Wendy? No, not really, I thought to myself. Maybe I'll meet someone else quickly, I thought, and spent the next couple of days focusing on the various websites. I went through all of my matches on one of the free sites. There were hardly even any new faces there in the two months I was neglecting the site to focus on Wendy. I browsed through about a hundred profiles on another free site. I even wrote one a message, a local 37 year old woman who seemed like she would be a good match for me. No response. I didn't even get a profile view from her.

I browsed through weeks of accumulated matches on Neil Clark Warren's site, sending a few of the less obviously wrong for me the 5 closed-ended questions that started off their convoluted meeting process, but even if any responded, I wasn't going to pay for the site, so I'd have to wait for the next free communication weekend to actually speak to anyone. My matches on the site where I met Wendy were all from the 'big cities.' Too far away, too short, too weird. No, no, no.

So, back to Wendy. It was three days later already. We hadn't spoken since that odd exchange Wednesday night. I needed to broach the subject of whether or not she was trying to tell me she wanted a sexual relationship with me. What do you do, come right out and ask? I shrugged my shoulders. What did I have to lose? What was she going to do, never speak to me again? I was thinking that that was what was going to happen anyway, and if I did make her angry and I never heard from her again, I wouldn't really miss her.

So I texted her. She responded quickly enough and we went through the cursory small talk. I eventually steered our conversation to what happened Wednesday night.

My friend thought that maybe you were trying to tell me that that was what you actually wanted to do to me, I texted her. I tensed for her reply. This was the moment of truth. She didn't respond for several minutes, and I got sick of staring at my phone and started to go about my business. Eventually I got a reply from her. 'lol' she texted. Was that a yes or no, I thought. I waited a few more minutes to see if she had anything else to say, but she was silent.

I started to think about our relationship, about how she never came right out and said anything, about planning our dates and how I ended up giving her a list of choices of things to do to pick from and she still deferred to me to say what we were going to do. Understanding dawned on me. Wendy simply wasn't going to come right out and say anything. If anybody was going to put casual sex out there, it would have to be me.

I think I would like it if you wrapped your mouth around my dick, I typed. I took a deep breath. I hit send. I stared at my phone, imagining her reaction as she read my text. Seconds passed, and then minutes passed. This was indeed a stupid idea, I thought to myself, and at least I ruined a relationship that was already over.

Finally the text box indicated she was typing. I stared at the phone, waiting for her reply to arrive. 'lol' she texted. Really, that's it? I thought. No wait, there's something else coming over. U would like that, she added. Well, it was an opening, I thought. Maybe we can meet up later, I texted. I'm not just giving u a bj, she replied. I would take care of you too, I typed. Hmm... she texted, and while I was anxiously awaiting her next text I wondered if she was really thinking about it or just pausing for dramatic effect. Buy me dinner first, she eventually said, and I readily agreed.

We're meeting up for sex, I texted Danielle. Good for you! She texted back. Go get laid! Do you have protection? I didn't even think of it. I went into my sock drawer where the condoms from my marriage were still hidden from prying eyes. The half of a pack of Trojans sitting there expired last November. Do condoms go bad? I texted Danielle. Lol go buy more, she replied.

I stopped at the drugstore on my way to dinner. I used to feel self-conscious whenever I bought condoms, even when I was married and we were just trying to avoid having unwanted children. This time felt a little different. Yeah, I'm expecting to have sex tonight, I thought as the checkout girl that probably wasn't half my age rung them up. I'm a stud.

We settled on the same Italian place for dinner. It was much easier than trying to figure out a different place we both liked. I decided that I should dress up nicely for the occasion, and I was wearing a polo shirt and khaki's. Wendy was dressed in a sleeveless blouse and a flowing polka dot skirt that went all the way to the floor.

Dinner had a different feel to it. There was an air of anticipation. On our dates I felt strangely relaxed. I enjoyed being with her, and I wasn't in any kind of hurry to get it over with or get anywhere with her. Tonight was different. Dinner was just a prelude to sex, and we both knew it. We ate quietly. I would smile at her sheepishly. She would glance at me knowingly. Then I would glance at her knowingly and she would smile at me sheepishly. Whenever I didn't think she was looking I would glance at her chest, at those enormous breasts that were contained in what must have been a heavy-duty bra. Soon, I thought, I would be able to see them, touch them. I squirmed in my seat.

Dinner lurched to an end. We got into our separate cars and I followed her to her place. We agreed on her place because she didn't have any pets. My overly friendly dog wouldn't leave us alone and would probably try to get involved in some way. She lived in one of the townhouses that have been springing up everywhere as our area got more and more built up. She pulled into her driveway and I found a nearby parking space. She waited for me by her door and led me inside.

The townhouse was nice on the outside but inside it was cramped and cluttered. There were toys everywhere. I felt a wave of anxiety. I half expected her son to come running down the stairs or something. She hadn't even bothered to clean up the house.

"Sorry about the mess," Wendy said, as though she were reading my mind. "Do you want something to drink?"

"No thanks," I said. I drank a ton of water at dinner, and what I really needed was a bathroom. Wendy pointed me toward the downstairs bathroom and I took care of business. I washed my hands in the sink, and then I found myself staring at my reflection in the bathroom mirror. I didn't look in the mirror much anymore. I was 40. I'd seen enough of my face. I noted the gray hairs around my temples and sprinkling the rest of my hair. The lines around my eyes, the skin that was starting to hang around my jowls. When did I get old? I thought to myself. It was an odd time for an existential crisis, I know, but sometimes you just have to stop and wonder 'how did I get here?'

I pulled myself together and left the bathroom. Wendy had cleared off the sofa and was sitting there with a glass of wine in her hand. She patted the empty space next to her. "Come sit," she said, "Make yourself comfortable."

I sat next to her, feeling awkward and anxious. I don't know why I felt like that. I knew why I was there, and what was about to happen. I noted that it was odd that I felt completely calm during our dates even when I was wondering whether or not I should kiss her, but now that the guesswork was over I was suddenly nervous. My body language must have shown it. I sat a short distance away from her, my hands in my lap, my shoulders slumped. My previous sexual experiences were all spontaneous, more or less. There was always a right moment, a right situation. This was my first experience with 'fuck buddies' and I realized I had no idea what to do.

Out of the corner of my eye I saw Wendy take a sip of wine and place the glass on an end table. She patted the space next to her again. "Come here," she said and she giggled. "You look so tense. Are you sure you don't want a drink?"

"I think I would like a drink," I said, and Wendy reached over and offered me her glass of wine. I took a swig. I couldn't stand the taste of alcohol and it made me sick to my stomach. I drank once a year on average, and even then it did nothing more for me than affirm my dislike of alcohol. It was fruity but bitter. I tried to avoid making a face but I couldn't hide my revulsion.

"You didn't like it?" Wendy asked. I could only shake my head no, still trying to swallow the wine, feeling it burn its way down my throat. "Aww," Wendy said, and she put her arm around my shoulder.

Whoa, physical contact. We had held hands a bit and shared a couple of awkward kisses, but this was the first time that Wendy had really touched me. I instinctively moved closer to her. She was large and soft, the complete opposite of my short and petite ex wife. I put my head on her shoulder and she gave me a squeeze.

We sat like that for a while quietly, enjoying each other's company. I started to relax a little, and I turned my head toward her. I found that she was waiting for me, and our lips met. We kissed slowly, lips on lips. I turned toward her, and placed my hand on her neck.

I realized that Wendy was rummaging around in her pocket. I broke the kiss with her. She pulled out a piece of paper. "Here," she said to me. I took the paper from her, puzzled. I opened it up and looked at it. It looked like some kind of medical report. I couldn't make heads or tails of it. I looked back at Wendy.

"It's an STD test," Wendy said. "I take it after the end of all of my relationships, just to make sure I didn't catch anything, and then I can show the next guy."

"Oh," I said. Romantic, I thought sarcastically. I kept staring at it. Everything said no or negative, so I guessed she was telling the truth. I had just figured I would wear a condom and I wouldn't have to worry about disease.

"What about you?" Wendy asked. "Do you have..." she started to say, and then thought better of asking me if I had been tested, seeing the look of utter confusion on my face. "Are you clean?" She asked.

"Well, I haven't been with anybody since my ex wife," I said, "And before her was 9 years ago. I don't even know, do they check for things like that at regular check-ups? I've had plenty of blood work done..."

"No worries," Wendy cut me off. "We'll just use protection."

Of course we'll use protection, I was thinking to myself. Even if STD's weren't a concern, I was going to take every precaution that I wasn't going to get her pregnant. Good god, what if I still got her pregnant somehow? Condoms aren't 100% effective, I thought, and broke into a panic. Maybe this fuck buddies thing wasn't such a good idea after all. Slow down, I thought. Nothing has to happen that I don't want to have happen. Maybe we wouldn't even have intercourse; I thought to calm myself down. We'll just use our hands on each other, maybe some oral. I didn't have to fuck her. I just wanted to get off, and get her off.

Wendy was shifting position beside me. She placed her hands on my shoulders and started rubbing them. "You're so tense," she said.

"Mmmm..." I mumbled, feeling her strong fingers press into my neck and shoulders.

"Feel better?" Wendy cooed into my ear. I felt her press her breasts against my back.

"Yeah," I said.

Wendy continued on for a couple of more minutes, and then she said, "Okay, my turn!" I felt her turn around behind me. I shifted around. Wendy was gathering up her long brown hair and pulling it away from her neck. I stared at her thick neck, red and freckled from too much time in the sun without sunscreen. I wrapped my hands around her neck and pressed my thumbs into her rough flesh. I heard Wendy exhale and felt her relax as I began to knead her neck and shoulders.

I massaged her for a couple of minutes. I needed to make a real effort to press my fingers into her thick neck and shoulders. Wendy was clearly enjoying herself though. She was breathing deeply and occasionally moaning contentedly when I hit a good spot. She rolled her neck around, and then she turned to face me, kissing me and pressing herself into me, pushing me back into the sofa cushions.

We kissed like that for a while. Eventually I pushed my tongue between her lips and found her tongue. We tongue wrestled for a bit. Wendy made a noise and shifted her position. She started pressing herself more against me. I started sliding sideways along the sofa.

Wendy broke the kiss. "Do you want to go to my bedroom?" She asked.

"Sure," I said. Wendy stood up and held out her hand. I took it and she led me to the stairs. I followed her up the stairs and into the master bedroom. I was relived to note there were no toys in there, but it was still a mess. The bed was unmade. There were clothes piled on the dresser and overflowing from the closet. The floor below the bay window was littered with dozens of pairs of shoes. The woman was a slob, I thought to myself.

Wendy pulled me close and kissed me again. I felt her hands behind me, reaching for the hem of my polo shirt. She grabbed it and started to pull it up and over my head. This was it; I thought excitedly, we're actually undressing! I pulled away so that she could get my shirt over my head. She tossed it aside. I took my undershirt and pulled it off myself. I reached tentatively for Wendy's blouse, waiting for her to stop me for some reason. She didn't. I took her blouse and pulled it up and over her head.

I stepped back to get a look at Wendy in just her bra. It was big and black, struggling to keep her huge melons in check. Wendy was reaching behind her back, and I watched as she fumbled with the hooks on her bra. She eventually got it loose, and pulled it forward and down her arms.

I gaped at the sight of Wendy's naked breasts. They were indeed shaped like melons, practically the size of her head. Due to their sheer size and obvious weight they hung down over her stomach. Her large brown nipples were pointed downward.

"Well?" Wendy was saying to me. The words 'what do you think' went unsaid but the insecurity was obvious in her voice.

What do I say? The sight in front of me reminded me of the ads you see on porn websites, older ladies need love too, or fuck a fat lady tonight. Wendy was an overweight 37 year old. Did I expect her to take her clothes off and look like Kate Upton? I glanced again at her huge sagging breasts and her protruding belly. I didn't exactly have a flat belly either, I thought to myself, and I'd been wondering what those enormous breasts would look like in the flesh ever since I first saw her picture on the dating site. I looked Wendy in the eye, and smiled. Yeah, I'm cool, I thought.

Wendy smiled back and started moving towards me. I held my hands out and grabbed her breasts when they were in reach. I brushed my fingers across her nipples. Wendy gasped and I felt her nipples stiffen. I took a firmer hold of her breasts and hefted them in my hands, feeling their size and weight.

"Do you like to have your breasts fondled?" I asked her.

Wendy shrugged. "Eh, it's nice," she said. "I know most men are obsessed with breast size. I don't get the fascination. For me they're just a bitch to carry around. What makes you so fascinated with my breasts?"

"I don't know," I said, still kneading and fondling her breasts. "Maybe it's an evolutionary thing, like our caveman ancestors thought the women with the largest breasts could feed more children."

Wendy laughed and I joined her. "I could totally see that," she said, and she pulled away from me and pretended to hit herself over the head with an imaginary club. "You can feed my children," she said in a mock caveman voice and we both cracked up laughing.

When the laughter died down Wendy said to me, "I want to see yours." I undid my belt and unbuttoned my slacks. I pulled them down and my underwear followed. My dick popped out, fully erect and pointing straight ahead. Even at 40 I could still get hard just anticipating sex.

Wendy was staring at my 7 inch erection as it bobbed in the air. "Not bad," she said, and she patted the bed next to where she was standing. "Lie down," she said.

My heart was pounding in my chest. My ex had only made one half-hearted attempt at a blow job the entire time we were together. This would be my first real blow job in nearly 10 years. I kicked off my slacks and climbed onto the bed, lying flat on the bed, staring at the ceiling. I felt Wendy climb onto the bed beside me. She leaned down over me and kissed me, her huge breasts pressed against my chest. She began to kiss her way down my body, my hairy chest and stomach. It was a quick trip. This wasn't romance, this was sex.

Suddenly Wendy's lips were around my cock. I exhaled sharply as I felt her take my full length into her mouth and start to bob up and down. I moaned as I felt her tongue moving against my shaft. Wendy definitely knew what she was doing. She pulled away from me with a plopping sound. "Ooh, I want to wrap my lips around your dick," she said in the same phone sex operator voice, and we both broke out laughing.

Wendy replaced her mouth with her hand, and my hips jerked when she ran her thumb along the sensitive underside of my cock, just below the head. I realized with all the excitement and the anticipation that I wasn't far from orgasm. Wendy was continuing to stroke me. I gave a louder moan to convey how much I was enjoying her attention and that if she didn't let up I might be about to cum. I felt something soft pressing against me. I was still staring at the ceiling, so I lifted my head to see what was going on. Wendy was using her free hand to press her breast against my cock. "Do you like that?" She asked. I moaned in response.

"I like it when guys cum all over my tits. Do you want to cum all over my tits?" She said.

"Yeah," I whispered. Wendy was still stroking me vigorously. Then she stopped and took one enormous breast in each hand. She pressed them against my cock and started rubbing them along the shaft.

"Oh my God," I said, and I went over the edge, my hips jerking. A huge spurt of cum flew into the air and landed on her left breast. A second and third spurt followed and covered her breasts around my cock. I continued spasming for another ten or fifteen seconds while Wendy rubbed her breasts against me. "Wow," I finally said, staring at her ceiling.