A Craigslist’s Encounter By Will Dawson
Dear Penthouse,
I am writing to tell you about the experience I had last summer while studying in the city. The first thing I did after getting my internet connection was to start browsing the craigslist ads. By the end of a full week of replying to the personal ads on craigslist’s I was so frustrated by the lack of positive responses I had gotten I began browsing the erotic services section as a possible alternative to my lack of action. At first it was just to look at the pictures though after a few more days of disinterest from the women in the dating section I seriously began to consider arranging a pro. I even went so far as to email a few of the girls to ask for more photos so I could make a decision about who to choose and to try and negotiate a better price. A few of the girls wrote me back with some more photos attached though my attempt at negotiations didn’t get me very far.
Two weeks into my attempt at using craigslist to get some free action I had been pretty much given up which is when I came across an unusual and very intriguing ad in the women seeking men category that soon after reading would prompt me to write one more reply.
The Search title read…Art School hottie seeks adventure (27)
Most of the description inside was pretty standard, it included most of the usual descriptors—cute, alternative, educated, single girl into yoga, art, Sunday’s in bed, hanging out in the park, and seeking slightly older interesting man…etc.
It was the third paragraph where the ad took an interesting turn—I am a sexually adventurous girl who loves to explore all aspects of her sexuality and would really like to partner with a male that has the same interest. Especially interested in dating men willing to explore MMF and strap-on play.
Since I was fascinated about knowing more about the kind of girl who would write such an ad, not to mention I had always been bi-curious, I couldn’t help but reply. To both my surprise and delight I got a reply from Sally, with her picture attached, the very next day asking for a picture or two of me which I promptly sent.
The picture she sent me was suggestive though not explicit. She was dressed in a pair of tight blue jeans and naked above her waist with her arms partly covering her breasts. She had mid-length dark brown hair with a slightly Eastern European look to her. Sally was the kind of girl who could hide her beauty by dressing plain though if you really looked you would notice she was down right stunning. I of course readily agreed to meet her for coffee—Thursday night at 8pm.
We hadn’t really discussed how things would proceed between us so despite my eagerness I told myself to play it cool. By the time I got to the coffee shop Sally was already sitting at a table. She was wearing one of those wrap around skirts over a pair of jeans plus a half Indian, half hippie, purple top. Unlike me, she was totally at ease from the moment I introduced myself. She then talked a little about how she was a struggling artist and I told her about the PhD I was working on. We also talked a little about our backgrounds like where each of us grew up and went to school and such.
After a slight pause in the conversation Sally grinned a little and said “My ad wasn’t quite like the others was it?”
“No, not really!” I replied honestly.
“So do you have any experience with men?”
“No, though I have been curious for a while.”
“Oh one of those guys eh, not quite sure they want to cross that line?”
“Maybe, perhaps I haven’t found the right guy yet?”
“Suuuurrrre that’s it, so what is your type?”
“Ahh.”
“Come on, you know!” Sally pressed.
“Okay I do, I would say…tall, dark hair, thin but muscular, successful, older…there was once this yoga instructor I almost asked out, I just wasn’t sure if he was gay.”
“I might have to see if I can find us your type, you never know what is just around the corner.”
“Keep me informed!”
Sally then leaned slightly towards me, looked me directly in the eyes, and said with just a hint of desire “So do you want to go back to my place or what?”
Trying to act cool I replied “Well it had crossed my mind.”
“Oh, just crossed your mind, so what you are not that into me?”
“No, um, I mean it is the only thing that’s been on my mind.”
“Now that’s what a girl likes to hear, so let’s get going already.”
Sally lived on the second highest floor in what could be described as a bachelor style apartment with a separate kitchen. Once inside she took my hand and walked towards her bed. There really wasn’t anywhere else to sit so I took the hint and pulled her down onto her bed with me. Despite the modest apartment Sally had super soft, probably rather expensive, sheets.
Once we were both laid out on the bed Sally rolled on top of me and began kissing me with a single minded focus. We kissed like that for a while and then Sally let her body fall to one side of me. At which point her hand was free to reach down and then undue my belt buckle, followed by my button and finally my zipper. Once she had created some access for herself she slid her hand down and grabbed my cock that already had begun to push it’s way free. Sally managed to free my cock completely from my cloths so it stood straight up at which point Sally began to ever so gently slide her finger tips up and down the shaft of my cock. The sensation sent chills flowing through me. After a few more gentle caresses Sally began rolling the tip of my cock between her fingers. It felt like magic to go. I probably would have cum if she had continued but instead Sally lifted herself up onto her knees. Then just when I thought Sally was leaning in to give me a very
promising blow job she hopped up from the bed and said “Just give me a few moments, I’ll be right back to take care of all your needs and more.”
I rolled over onto my stomach in a moment of frustration, closed my eyes, and tried to find a calm patient place in my mind. I heard Sally came out of the bathroom a couple minutes later. However, since I was lying on my stomach with my head turned sideways I didn’t notice until she was lying next to me that she had fitted herself with a black leather harness which held a large purple silicone cock. Before I had a chance to comment on her new look she was slipping her tongue back into my mouth. She then kissed her way to my ear while using her hand to play with the back of my neck. She certainly had me all revved up. After sucking my ear lobe Sally whispered in my ear “I want you to suck my cock!” Sally then lied down with her back to the bed and cock sticking straight up in the ear and waited for me to go down on her. I of course had a choice to how to proceed though it wasn’t long before I was on my knees and very willingly indulging Sally’s
request.
Sally urged me on “Ya baby take it all” as I tried to fit her cock in my mouth.
Sally added “Oh ya you are making me sooo hot, I think I might come in your mouth, I bet you would like that!”
Just when I had got used to the girth Sally said “Okay baby that’s enough, it is time for me to return the favor.”
I immediately rolled onto my back with my legs extended over the bed slightly and with my cock still very much at attention. Amazingly Sally took my whole cock into her mouth with ease. In doing so her lips pressed against my shaft which made me shudder in the deliciousness of the sensation. Each time I felt my cock hit the back of her throat I thought it would send me over the edge. I managed to hold off though I knew it wouldn’t be to long before I filled the back of her throat with my steaming hot semen.
Just when I was beginning to really loose myself in the delicious blow job Sally was giving me she pulled her lips off my hard cock to say “Okay so I think you are ready for me to make you a new man!”
At which point she got off her knees, grabbed the bottle of lube from beside the bed, and heavily greased her cock one last time before re-positioning herself so she could enter me while my legs still hung over the bed and rested on the foot stool. She had, unknowingly to me, strategically positioned me so she could easily fuck me.
Just the sheer size of her cock overwhelmed me when she first pushed herself into my cavity. I pleaded with her to be gentle. I could tell it wasn’t her first instinct to be kind in this situation though she did seem to restrain herself as best she could. She gave me nearly a minute to get used to her girth before pushing deep, deep inside me. I was surprised at how hard my cock had become despite the pain like sensations I was feeling.
After pausing for a moment to re-lube her cock, Sally began to slide her cock deep in and then almost all the way out of me and then back in me, again and again. The whole time she used one hand to steady her cock at the base. Sally began to use her free hand to jerk me off simultaneously as she fucked me. I had never felt so much fuckin intensity in my life. I thought I was going to pass out in pleasure. When Sally felt my orgasm bursting out of me she pushed her cock deep inside of me and held it there while she furiously jerked my cock. I cried out as I climaxed “I can’t stop it.” At which point sticky hot fluid oozed out of my tip, which Sally was gripping with her hand, and into her fingers. When I finally stopped shaking from my orgasmic experience Sally pulled out of me.
While I rested for a few moments Sally excused herself to get unharnessed. When she came back she jumped on the bed beside me and said “So how you feeling?”
“Like a high school cheerleader who just got pinned for the first time by the quarterback on prom night!” I whimpered.
“Oh that is a hot image, so I guess you liked it!” Sally said with a grin.
“It was intense that’s for sure”
“So listen I have an early morning, like normally I would get you to return the favor but I think I am just going to get myself off while you shower okay.”
“If you are sure that’s what you want?”
“Ya I am sure, don’t worry you will get your chance to have me soon enough!”
While I was waiting for the elevator to take me down to the street I couldn’t help but wonder if I would ever hear from Sally again. Perhaps it was just her thing to take a guy’s backdoor virginity and move on to her next girl-a-fication target. Perhaps playing out a kind of reverse victimization fantasy was her intent all along, now I didn’t feel like a victim though perhaps that was her modus operands. She had certainly got me to play along rather effortlessly. Needless to say I was anxious to see her again despite my doubts on it happening.
At the end of the next day after getting back from class I checked my email hoping to see a message from my new friend. Unfortunately she hadn’t sent one yet so I had no way of gauging her satisfaction from the night before. I wrote her a brief message saying how much I enjoyed our experience and would luv to see her again soon. At that point all I could do was wait. Since I had no plans, for this particular Friday night in my new city, I decided to organize my email a little. It was during this process where I was shocked to discover that the email Sally had sent me was from the same address that MsBlue, one of the escorts I had written, had used to write me back from craigslist. There was of course only one possible explanation—Sally was a pro. Like a crazed maniac I went through MsBlue’s web page. Unsurprisingly her page advertised how she offered strap-on services for men with such interest. Perhaps a little more surprising she offered her
services along with a male friend for men who wanted to experience MMF threesomes. She also quite plainly stated how she was disinterested in women. Her services were offered at 500$ per hour with a 2 hour minimum. She also stated she only saw one client per night.
It took me half the night to process what I had just discovered. I basically decided I could hardly complain since I had gotten her services for free. I certainly didn’t expect that she was celibate before meeting me and we didn’t have unprotected intercourse so I wasn’t all that worried about std’s. Plus, I had freely chosen to jump in bed with two feet first. My mind turned more to the future. What did Sally or that matter Msblue have in mind for me? Not only that but perhaps more importantly how would I broach my new found knowledge with her? I quickly realized I might not even get the chance. I anxiously checked my email the rest of the night. I couldn’t help but wonder if she was too busy with a client to write me back.
It wasn’t till late Saturday afternoon that I got a message from Sally. She wrote how she also had a great time and wondered if I wanted to have Sunday brunch and then perhaps go back to her place for some afternoon adult recreation. I wrote her back right away telling her to just name the place and time and I would be there. Looking back I admit part of me wanted to ask why she couldn’t get together that Saturday night though I was pretty sure I knew the answer to that question and I didn’t want to lose my chance to see her again by being too invasive and/or needy.
At brunch I tired to act causal though by the time we were done eating Sally who must have sensed my inner turmoil took a deep breath before stating “So I guess you figured out what I do for a living other then my art, you know I just realized this morning I had written you back using my discreet email, I kind of guessed you would put it together sooner or later, so how do you feel about it, you’re here so that is a good sign I guess?”
“Umm honestly, well like morally I have no problem, though you know I can’t say I have much experience dating aaah…”
“Hooker, call girl, escort, or companion…I am okay with any of them.”
“Okay call girl, I don’t have much experience dating a call girl.”
“Ya I understand, I want you to know I am always very safe and get tested nearly monthly.”
“Well that’s certainly reassuring to know.”
“And so besides that, could you be with me?”
“You know, could we just take it one step at a time, it is a lot to take in and consider.”
“Okay, sure, that’s fair, so do you have any questions you are just dying to ask?”
“Well are you going to be asking me to go on calls with you?”
“Ah well, not unless you ask me to—is that something you would be interested in?”
“You know, no girl has ever asked me that before?”
My comment made us both start to laugh. Before I got a chance to actually answer her, the waiter had returned to settle the bill, so I just let the question rest. Once Sally paid for brunch I followed her back to her place.
I was expecting another hardcore session with Sally taking the lead though from the moment we entered her apartment I could tell she had something different in mind.
At first she lit candles and put on some funky 70’s music before slipping into the bathroom. This time she came out dressed only in her panties with her succulent breast fully exposed though of course minus the bend over boyfriend gear.
While I finished folding my pants Sally lay on her stomach beside me. Once I unbuttoned and removed my shirt I placed my hands on Sally’s back and began to explore every inch of her delicious figure. I tried to worship every curve she had with my fingers as I moved my hands over her entire body. Each kiss I tired to seduce her soul into surrendering to the absolute delight of orgasm.
I was trying my best to hold back from going near her privates, she knew of course I was teasing her, so when she moaned “kiss me” and then rolled over, I knew she didn’t mean on the mouth. I had built up the suspense long enough so dutifully and wantonly I ran my tongue across her cunt. By the time I had repeated the motion 8 or 9 times Sally was beginning to squirm. I then pressed my face even further into her with the intent of securing a little death. As my tongue melted against the heat of her clit Sally’s body began to explode from within. The fireworks of temptation captured were resulting in a painful moment of satisfaction eased only by the pleasure of release. Sally shined more of herself across the room with each trembling wave of wicked pureness that poured through her every delicious nerve.
I was so in awe of how much she had let herself “just be” in the moment I didn’t quite know what to do next. Like her usual self Sally made sure I knew which direction to take by reaching her hand down between my legs to stiffen me up. When I was ready she pulled me between her legs and on top of her and then whispered in my ear “Gentle isn’t necessary.” Her statement in itself nearly made me explode right then and there though by taking a deep breath I delayed the inevitable.
Sally was so wet I slid right into her with little need for adjustment. Despite her earlier statement I started gently though as I could feel from her physical reaction she was definitely ready for more. My eagerness soon got the better of me and I began to unleash my inner beast and rapidly found myself pounding harder and deeper into the women I so was falling in love with. I made an effort to breath deeply hoping to prolong the ecstasy of our animalistic ritual. As my thrusts became harder and harder Sally began to clinch into my shoulders with her fingernails which only made me more aggressive. In a way she seemed to be taping into my inner being and tempting me to go even further into my unexplored inner beast then I had ever had before. The pleasure I was feeling was so intense it blinded me to the realness of the situation. I had become a warrior and Sally was the princess I had captured to be at my side. Sally began screaming though I didn’t know if it was in pain or pleasure—the truth is I didn’t care. I had become lost in the bliss of sexual rage and just when I owned my animalistic delight the waves of climax rolled through me like the thunder of a storm and I came more deeply then I had ever had before. And then instead of feeling the regret I would have guessed was coming I shockingly felt a oneness not just with myself but with Sally—somehow all my anger became kindness and all the darkness inside disappeared into the lightness of truth. I felt more complete, and whole, and worthy just when I would have thought I would feel the opposite. The unity I felt lead to tears. I was overwhelmed with emotion and soothing. I could feel myself shaking in the honesty of the moment. In what seemed like the longest time I felt truly vulnerable in the moment. In itself my vulnerability was calming and even enjoyable something I couldn’t have imagined it to be previously.
At some point I had rolled over and Sally had begun stroking my arm in approval. When she sensed I was a little more coherent she nudged me and said “Now that was Fantastic.”
“I didn’t hurt you, did I?”
“Only in the good way”
I started to speak “I …” though Sally put her hand on my mouth and said “Shhh you didn’t do anything wrong…now just be, enjoy the bliss” and with Sally’s words we both fell into a deep sleep and had dreams of togetherness.
------------------------------
We kind of got into a routine over the summer. Thursday we would have dinner and then Sally would fuck me. Sunday’s we would spend the day together and then Sally would more make love to me. That’s how things went till the seventh week. That Thursday after our session Sally told me she might not be able to see me Sunday because a client had booked her for the whole weekend. By that time we had exchanged cell numbers so I just said call me if you are free, I would like to see you.
I admit I spent that Friday feeling disappointed I wouldn’t be able to see Sally Sunday so when I got a call at 530pm and heard Sally’s voice I was pleasantly surprised. I could tell right away just from the way she said Hello Sally was anxious about something. “So what do I owe the pleasure?” I said. Sally replied “Listen I have something to ask you, just hear me out before you answer okay, so I am suppose to meet a client in his suite for dinner in 15 minutes, the thing is he is expecting me to show up with Jason, and Jason just called to say he can’t make it cause of the stomach flu, normally I would just tell the client what happened, the thing is he has already agreed to pay the both of us 10,000 for the weekend, so I would of course split it with you, and don’t worry I already discussed it with him, he is not into male anal he just wants to kiss and touch a guy a little, and if anything needs to be swallowed I will take care of that,
plus he is totally your type, tall, fit, dark hair, so ya you can totally say no of course, I would like to give you some time to think it over, but the thing is I really need to know like in the next five minutes, so what do you say Will you play for pay?”
Cum on out to the show tonight: Nightwood and friends rock out at Jupiter Room! More info on the show here. Also part of the first place prize is the latest issue of Lickety Split as well as two tickets to the show!!
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