"Kiss me," she said. My heart flipped at her demand.
A cold breeze was blowing, chilling us both through our winter clothes. A shiver ran down my spine. I couldn't tell if it was because of the situation I found myself in, or the cold Kentucky night. I leaned in and kissed her, cautiously, exploring her lips with my tongue gently. I could taste the wine she had been drinking and her lipstick, which only made the moment more erotic. As I stepped back, we stared at each other. A nervous grin crossed my face.
"Do you want to fuck me, John?" she asked, her voice barely above a throaty whisper. Then as I was almost dumbfounded, she added, "Cutie-pie?" making sure my eyes were on hers.
"Yeah ... I do..." I nodded in reply.
She grinned. "Follow me, then..."
As we walked, making small conversation, my mind ran over how I found myself following this near total stranger back to her room. My girlfriend had left me six months prior, leaving me just to have fun with my guy friends. But really my mind had been made up; I loved pussy, and after my first taste with my girlfriend Sara, I knew I had to have more. I wanted someone more experienced, which really I did not know how to reach out to, so it left me depressed. I moped for the better part of five months, trying to find some way to really be taken seriously for my love of an older woman, not only as a sexual lover, but as a LOVE. Finally, I made a resolution to myself: I was going to party it up more. Be less uptight. More fun. More outrageous. More sexual.
I turned my computer on almost immediately and posted an ad on an adult "dating" website, complete with picture. I toyed with what I wanted in my mind. My ex-girlfriend had been fun, but more of a voyeur then anything else. She liked watching me with Steven or Dave, and she would play with herself and just need me for that final release. I knew I wanted someone loud and exciting. Willing to try anything. Someone totally debauched. Someone with experience to spare. I thought up labels for people, based on the porn I watched. I said I wanted a MILF, a Cougar, someone into all sorts of kinky shit without being specific. I said I wanted a cougar or MILF to teach me how to please her in all of her favorite ways. I wanted to be her boy toy.
I certainly got what I was looking for in Nicole.
I was working at my job when her email came. Whenever I got responses, I lost all concentration and had to analyze the email in total detail. This time was no different. Most of the time I was disappointed, either old gay guys looking for a quick fuck or spammers looking to add an email address to their collection.
When I glanced down at my phone to see who had emailed me, I felt myself stiffen immediately. She classified herself as a BBW. And though I loved thicker women; women of shape and curves, I knew that some that called themselves BBWs were not really what those initials spelled out for me. Big Beautiful Woman - some were BIG alright, and the thought of fucking a whale made me positive I wasn't going to respond. She said she was as kinky as they came. Her email said she was a squirter. That was about it. I closed the email and went back to work, disappointed that my fantasy girl hadn't messaged me. After all, I had put some thought in my ad, I had written more, and all this chick did was say that she was a BBW and a squirter, it really did not seem like a good fit.
When I got home after my TaeKwonDo practice, I went through my usual routine, meaning grabbing a quick bite to eat and watching porn. My mind immediately went back to the email since I hadn't received any others. Curious, I began watching some BBW porn. I unzipped my pants and began stroking myself, watching a large woman devour some guy's cock. Yes this way I could choose the BBW that I was stroking off to - the chubby ones, the chunky ones, sometimes the sites said fat, but they were not fat at all. Round and big tits, not fake, but mmm I was getting hard, and actually had made myself cum two times.
I clicked on a couple more videos. Big women with nice round bellies and huge tits performed all sorts of debauched acts on my screen. I came one more time and tucked myself back into my pants.
"Oh well, those are porn stars. I'm sure she looks like an ogre." I tried to bring myself to the reality and truth of what I have found out so far.
The next day mom dropped me off at work, because she needed the car later. I couldn't stop thinking about what I had seen the night before. Could there really be a woman with big tits and a full blown sex drive for me? I opened the email again. I felt myself stiffen again. Before my shift started, I sat down in the bathroom and started typing a reply.
"Hi there, I really hope you're still interested. You sound really sexy ... I'd love to chat with you on Yahoo Messenger or texts sometime. Add me or text me any time." I thought about it, and it didn't seem enough, so I wrote more about me. About me being bi, about not being experienced, about my secret kink of wanting to suck on a woman's breast until I could really taste her milk. (Oh, I was getting hard just writing about it.) I figured I would not hold back and if she was the one for me, she should know, I was putting it out on the limb sort of. Again, I thought about the brevity of her first response, and I knew it did not deserve the e-mail I was sending now, but I wanted to reach out. I was in full blown HOPE at this point.
I sighed nervously and went out to the stock room. Hours passed. Despite checking my phone every five minutes, no reply came. I put it in my pocket and tried to forget about it. Just then, I felt it vibrate. My penis immediately stood erect. She had added me on Yahoo, and sent me an IM! My heart was racing. I clocked out and took my lunch break an hour early.
I looked at her message: "You sound really desperate, lol."
biJohn: "Haha, well, I missed your email. I was really hoping you hadn't lost interest."
39BBW4U: "Not at all."
The next half hour was the most awkward conversation I'd ever had. I'd never done this before, and I wasn't sure how to act suave or cool to someone that much older than me. Thankfully, she saved me by cutting to the chase.
39BBW4U: "So tell me what sort of kinky things you're into, John."
biJohn: "Anything you want me to be in to ;) I want you to tell me exactly what you want. I want to lick you for hours so you can squirt down my throat. I want to please you with my tongue, my lips and my teeth - my fingers and of course my cock too."
39BBW4U: "Mmmm ... what if I told you I was masturbating right now?"
Shit, I had to do something about this. I was rock hard. I sneaked into the bathroom and all the stalls were empty. I undid my belt, unzipped my pants, and started jacking off as fast as I could.
biJohn: "Now look what you made me do ... I'm in the bathroom touching myself too."
39BBW4U: "Oh fuck that's hot. Rub yourself for me, baby. I want a picture of your meat."
The luridness of her statement made me cum almost instantly, out of nowhere. I hadn't cum this hard in months. My jizz sprayed out all over the toilet seat. A single bead dripped down my still throbbing shaft. I quickly snapped a picture of it and sent it to her and licked up all my cum
39BBW4U: "Oh fuck that's so hot, I'm gonna cum too."
biJohn: "Mmmmm ... My cum tastes good too, I would love to share it with you."
She logged off at that point and I didn't see her again all evening. The next morning, I awoke to an apology in my inbox.
"Sorry, cutie-pie, the battery on my Blackberry ran out last night. I'll make it up to you, though. I'm going to call you at exactly 6:00 PM today. Don't pick it up. -Nicole"
My mind was racing. What did she plan to do? Leave me a message? Six o'clock couldn't come fast enough.
Sure enough, at 6, my phone rang. I was working when it happened, and I had totally lost track of time. I immediately excused myself to take a break and went back to the bathroom. I immediately checked my voicemail. She had left me a four minute long recording! I hit play and listened intently. She had the voice of a professional phone sex worker. I was practically salivating...
"Hey cutie-pie ... I'm naked in my bed and I'm soaking wet."
I stopped the recording. I listened if there was anyone else in the bathroom with me. I was hard and so I pushed my pants to my ankles and had my hand on my cock as I listened to the full message.
"Hey cutie-pie ... I'm naked in my bed and I'm soaking wet. I'm going to tell you all the things I'm going to do to you. First I'm going to strip you down and swallow your hard cock. Mmm ... I'm going to lick your shaft from base to tip and then suck on your purple head. Fuck, yeah. I'm going to keep going, fucking your cock with my mouth until you cum all over my face. You want that, sex toy? Yeah ... Mmm..."
I was masturbating furiously. I was so hard it hurt.
"Then I'm going to get you hard again and bend over in front of you. You're going to stick your fucking cock inside of me and fuck me until I squirt all over the floor. Oh, fuck yeah. Fuck! Mmm..."
The rest was three minutes straight of carnal, erotic moaning. She screamed into the phone as she came, and I came with her. I cleaned myself up and sat back for a moment before heading back to work. That was the sexiest thing I had ever experienced. It was official, I needed to meet this woman. I needed to fuck her. And it needed to be soon.
As I stood in her hotel bedroom, Nicole lay spread eagle in front of me. Despite the nervousness I felt, I was rock hard. This was totally uncharted territory. Was this right? This woman's older than me -- much older than me. I don't even know her. Should I just leave? What should I --
"Fuck me!" Nicole commanded, breaking my train of thought. I stood, dumbfounded. "Come and fuck me, hard. Now." She wasn't playing around. I got on my knees and moved in towards her. I leaned forward and felt our stomachs touch, followed by my cock pressing against her soaked pussy.
"Shove it in me!" she demanded. I did as she said, and I slid my cock inside of her. She immediately moaned in delight as I filled her to the core ... Every time, it was like when we first met.
This was the tenth time I had met her in her hotel, and she was still leading me around like a puppy.
The next two days felt like they took weeks. Every morning I'd awake to another incredibly sexy email from Nicole, my cougar BBW. We discussed our fetishes in depth with each other. What a coincidence -- we were both absolute freaks. I said I liked lactation, and she said she had always wanted to induce and make her tits fuller then they already were. She also said loved pissing on guys (which I wasn't that much into); I said I had a thing for squirters, she squirted gallons at almost the slightest touch. She said she loved facials and cum on her tits, I told her I would love giving her all my cum. I said I wanted someone to teach me how to eat pussy, she was happy to oblige. We had incredible sexual chemistry.
When she finally sent me a picture, I was flabbergasted. She wasn't some gigantic monster at all, but a voluptuous, sexy, curvy woman. I steeled my resolve and sent her an email back.
"That does it, I can't take it anymore. I need to meet you as soon as possible. Are you free this weekend?"
I gulped and hit send. I hoped she'd get back to me early, I couldn't take the suspense. Sure enough, at 5 PM, when she got back from work, she emailed me back.
"Ooo, taking command now, I see? I'm not far from Louisville, I will drive in, and can you meet me at the Starbucks in the Highlands."
My heart sank. I was terrified of this situation, my brain said no, it's too dangerous, but my rigid cock said otherwise. I needed this woman, I needed sex, I needed to cast the memories of timid, silent, nearly motionless sex with my ex-girlfriend out of my head. I sent her quick email back and said I'd be there at 7:30.
When the appointed hour arrived, the feeling of nervousness had only reached a crescendo. I didn't think I would even be able to get it up, much less please this woman. What if the picture was a fake? What if she was a transvestite or something? My mind was racing.
"John?" I heard her voice behind me. I gulped, and turned around. There she was, as alluring as the picture. Her hair was wavy and down to her shoulders. She wore bright red lipstick and a gray skirt. The cold air made her nipples stand out from under her shirt and GOD were her tits big!!! She was certainly a BBW accent on the BEAUTIFUL; the picture had been slimming, for sure, but she was still incredibly curvy and especially sexy.
"You must be Nicole." I grinned, trying to play it cool. I hoped I wasn't giving away how fucking nervous I was. I felt like my knees were going to give way. Again, would I even be able to stay hard enough to fuck her?
"You got me." We stood, looking at each other, not sure of what to make of the situation. Realizing my nervousness, she took control, thankfully. "So ... do you want to go out and get something to eat or have a drink here, or just head back to the room I got?"
I was so nervous the thought of eating made me feel even more sick, as did the thought of drinking anything. "Back to your hotel would be great, I guess." I replied, still trying to sound suave.
She smiled, nodded, and said, "This way."
"Shit, I'm being way too forward here," I thought to myself. I followed her down the street and around a corner. There was a hotel close, and she must have walked here. Just outside the side door, before she slipped her card key in to let us inside the building, she turned to me and looked me directly in the eye.
"I've been waiting all evening for you, y'know. I've had more than a couple of glasses of wine. Do you want to fuck me?" she whispered throatily at me.
I gulped yet again, and nodded. "Yeah, I do."
"Kiss me, then."
I sucked in a deep breath of the cold air, leaned forward, and kissed her on the lips. Only the third woman I'd ever kissed, I was still keeping track at this point. I wondered if it was too late to run away at this point and stand her up. Then her tongue parted my lips. She kissed me, deeply, sensually. I pressed back with my tongue, entangling them in our mouths. We played back and forth for what seemed like five minutes. I could taste her lipstick and her wine. It was a heady sensation.
She smiled at me and moaned, clearly aroused. I loved how she pushed her boobs into me fuller and more solidly as the kiss lingered.
"You're a fantastic kisser." She said. I grinned, stupidly, not sure of what to say. She turned, opened the door and then went up the stairs. I was watching her butt as she was in front of me, I knew she wanted me to, and I couldn't help myself. She unlocked the door and stepped in. I was glad for the warmth of her room. It was a suite, nice and clean.
"Nice room." I managed. She laughed as she walked over to the desk and poured herself another glass of wine from a bottle that was half full.
"Would you like some?" she asked.
"That's alright, I don't really drink."
"I see..." She took a large gulp and motioned for me to sit down on the couch. I did so, and placed my hands on my knees, awkwardly. She sat beside me and placed her wine on the table.
"So ... what do you want to do?" she inquired. I shrugged, not really sure what the right answer was. What was the proper protocol for a situation like this?
"Do you want to watch TV, or a movie, or something ... maybe some porn?" She looked at me, mischievously. "Or do you just want to talk?"
Truth be told, I was interested in watching some porn with her. A woman as kinky as she claimed to be would probably be into some really interesting stuff. Not wanting to sound as forward as I had been before, though, I cleared my throat and sounded out, "Let's talk."
"So, John, I know what you do, you work at Best Buy. But you don't know what I do, do you?"
I shook my head. "No, I have no clue."
"Take a guess. What do you think a person like me does?"
"Um ... I really have no clue. What do you do?"
This was so awkward for me. Was she judging me? Was she going to look into the answers I was giving and figure out how I felt about her?
"No, really, come on, take a guess." She continued smiling that mischievous smile.
"Uhhh ... Medical Nurse?"