I would like to say I had a sob story, but like most people I am over dramatic about my own life. I grew up in a good home, until my parents divorced when I was in 6th grade. While my parents were both supportive and loving, I lived with my mother and missed out on a lot of Man time with my dad, so I never learned the unlimited self confidence a lot of guys have.
I have seen many guys who were ugly, broke and balding still have no trouble going up to any woman they liked. I wish that was me. I had two girlfriends in high school, a couple in college and a couple through the years. I am a pretty handsome guy I have always been told, and I have great hair and eyes.
The relationships I had were fine, but most were relatively short lived. The longest one was a year or so and she had checked out a few months earlier. The issue of my low self confidence was partly not having my pop around a lot, partly due to never being good at earning money, partly due to being to smart for my own good (and talking myself out of things) and partly just my introverted personality. Once I was comfortable I could chat up almost anyone, but for some reason, even now, at 42 I got tongue tied and nervous around pretty women, especially the younger ones.
I would see the local college girls often on my walks around town and I wished somehow I could get one. I didn't want a whore, though I did turn there for a while. I usually went off Craigslist, and then Backpage because it seemed to be the only place young ladies could be found.
While I am decently handsome, I have never been much of a workout guy. I was a bit soft all around, a few extra pounds but not much. I am only about 5 foot 8 and my dick, while a decent almost 7 inches erect, was a grower and not a show-er, and it matters. Or seems too. I had impressed a few women in my time, and once a pretty hot one but when they saw my small size flaccid, it killed enthusiasm.
One expensive hooker, the one time I blew my Christmas bonus, did an over night. We had a decent first run and the next morning as we awoke she said she had a Christmas present for me and pulled the sheets down to blow me only to stare at my barely 2 and a half inch softy and suddenly didn't seem to want to touch it. Though she knew I had decent length hard, again, it seemed to matter.
So while I had dated a few women and seen a few hookers, no one ever seemed impressed by my bedroom talents. They seemed to like me, but something was missing. For a while I was visiting some Asian massage parlors, and through the thin walls I could hear some gals moaning from the good fucking they were getting. They never made noise with me, even if I could tell they liked who I was, I wasn't getting anyone off.
That further deflated my confidence and left me 42, with a shitty job, no real prospects and a sadness that I would never have a woman I really wanted. A young, sexy, feminine bombshell. Even the hot women hookers I had seen were obviously in their late twenties or possibly even the early 30's. That was annoying. Then the next year, everything broke my way.
I had been writing a novel in the evenings and weekends and when I finally finished and sent to publishers I was elated that one decided to ink a deal with me for royalties and a initial payment of $50,000. I quit my job to write more and the royalties from my first book started to roll in. I continued to frequent the AMP's, as I really dug Asian women and they usually seemed to be at least under 30 years old in those places.
But it was still a very detached sex life and even with my success now and a career I could be proud of, I still didn't feel very confident. Later that same year my book crossed a sales threshold and they asked for a sequel and offered me a $300,000 signing bonus. That was wonderful but after my student loans, credit cards, a new modest car and a 3 bedroom home bought free and clear, I was broke again, though the royalties kept me at about $2400 a month.
I finally got the second book finished and this one was an instant hit. I got a better royalties deal this time and while I was hopeful for another nice bonus for the third book, at least my monthly stipend was closer to $4000 a month. That was when the website What's Your Price got my attention. If you don't know, it is a site where women can auction themselves off for a date. You probably think what I did: some hot young college coeds who need money, and know they have a valuable asset sell a night or hour or however long of passion in exchange for a nice sized cash payment.
I was excited when I found the site. I thought I could finally get the kind of pussy I really wanted, and had plenty of money to burn. I bought a new suit and took some pictures and mentioned that I had plenty of money to play with. At first I was kind of disappointed as most of the women rejected my flirts, apparently they wanted marriage minded men who were gorgeous and rich.
Really rich. I could give them $500 for a good time but they wanted ongoing relationships for $1000's a month. The really attractive ones even wanted a base AND extra for every meet up, not to mention an apartment. Though frustrated I kept at it and finally found two different women.
One was a mixed French and Filipino and the other was a Latina, both were insanely attractive. The first was only 18 and the other was 22.
Suffice to say, I was incredibly excited going to both dates as I figured after a nice dinner I would get to fuck these beauties and maybe get an ongoing thing going if the price was right. Instead, both dinners were an hour and a half or so at a very pricey restaurant and they $300 and $400 price I agreed to was what they demanded just for the date.
The first one, the half Asian, seemed bored the whole time and as soon as her dinner came she scarfed it down and grabbed the envelope and left saying maybe we would meet up again.
But we didn't. The second gal I wised up a bit. I told her she had to give me her phone number first. She did and we talked a few times on the phone. I told her in no uncertain times that I was willing to do $600 flat for the date but it was entirely dependent on her coming back home with me. She told me that was fine but that I had to bring the money to dinner to prove I had it, she was afraid of getting stiffed.
The first gal had been pretty, though she was obviously using photos from a few years ago, and had used flattering angles and maybe even photoshop as her skin was just average. But this second girl, the Latina, she was the real deal. Five foot two, thicker but fit as could be. Long jet black hair, big eyes, typical outstanding Hispanic breasts that threatened to pop out of her top, which was very tight and low cut black mesh, and her tanned brown legs in high black heels in a black mini skirt floored me.
We met at the bar, where my shyness was instantly taking over and there is no doubt in my mind she quickly knew she had the upper hand. She laughed at my jokes, put her hand on my thigh a couple of times, gave me coy smiles.
By the time we sat down for dinner I had a raging hard on under the table. I was having trouble even conversing as all I could think about was getting her home, tearing off those tight clothes and trying to hold my cum in for more than a few seconds. I would definitely see this one more than once. Part way through dinner, thoroughly convinced she was the real deal, she asked to see the cash to be sure I was legit as well. I slid an envelope over with the $600 and she checked it out and put it in her purse.
I was happy to see the desert cart show up, I was ready to get out of there and have the real desert. She passed on a desert as did I, glad to get moving. I asked for the check and before it arrived she stood up and said, "this was great, but I have to be up early for a photo shoot tomorrow. Send me an email and we can see if we can move this forward." "Wait a minute", I said, trying not to get angry.
"We had a deal, that cash was for the whole kit and caboodle, not just dinner!" I kept my tone hushed, she did not. "What do you think I am buddy? Some kind of fucking hooker? No I won't just fuck you for money!" She said it very loud and everyone was looking at us.
I was so embarrassed my ears went red and my head drooped while the gorgeous young tart walked out the door. I paid my check quickly and left, mortified. I went home to write a scathing message to her and then did the same on my own profile, saying I was done with this bullshit, paying huge money for a single dinner date was stupid. Then I promptly went to her profile, saved her photos and took my laptop to my bed and jacked off looking at her pictures and imagining the fuck I thought I was going to get from her.
Needless to say, I came really hard. I thought of ordering a hooker, an expensive one, but I was tired of professionals, I wanted a woman who wasn't fucking 50 other guys a week. That was the last I thought about the site for 6 months. Then I suddenly got an email saying a gal had favorited my profile and sent me a wink. I ignored it for a few days but curiosity got the better of me and I logged in. I clicked on the link and it went to her profile.
She listed herself as 22, no kids, never married, was going to school for marketing and music promotion. She wasn't jaw droppingly hot like the types I had been hitting up, but she had a very girl next door quality and I loved the way she dressed in her pictures.
She was 5 foot 5, she had bleached blonde hair, b cup breasts that weren't overly attentive but did the job. Her legs were a tad bit on the thick side, but still very feminine, and her face was a cross between a nordic woman and an italian woman. Dark eyes and eyebrows, thin lips and a button nose. She actually reminded me a bit of Chip and Dale with her nose and the way her eyes were placed.
I don't mean to infer she was unattractive, she was very cute, in that scrunchy face. Her smile was what sold her though, it was perfectly symmetrical with blazing white teeth. Like I said she was no model, but she was plenty desireable and she wore a skirt or dress in all her pictures and always had her hair done a different way. Lipstick and eye shadow, the whole nine yards.
I still had some credits on my account so I sent a modest $150 bid and got an accepted reply almost immediately. I used the last of my credits to unlock the messaging and contacted her. I was nice but firm in asking if she had read my profile.
She wrote back that she had and that was why she contacted me. She wanted a no nonsense guy who wasn't looking to date, because she wasn't. But since she wasn't ethnic or with dark features she didn't think I would bid for her. It's hard to explain, but the way she wrote seemed so much more sincere than the others I had conversed with. She seemed genuine in her interest in me and it was obvious she had read my profile thoroughly as she mentioned the bands and movies I had listed as favorites.
I didn't want to beat around the bush so I asked her if she had read that I was tired of paying just to have dinner. She wrote back that she had. I asked if she was willing to do single night dates. She said she thought so, but wasn't sure she knew what I meant. So I finally wrote back that I wanted a per visit sugar baby. She wrote back to me "I had a sugar daddy before, that was why I originally came on this site. That plus your not expecting a regular date sounded just right to me." I was a little stunned.
For the first time a girl seemed to be telling me she was willing to be a amateur whore for hire. That was definitely what I wanted, and while not really my type, she was worth fucking for sure. If she was half as sweet in person, it would be worth every penny. I wrote back that everything sounded perfect. She wrote back that she though so too and asked if we could meet for dinner the next week. I checked my schedule and so did she and we agreed on the next Wednesday because she had no early classes on Thursday.
I actually make my own schedule but didn't want to say that as I didn't give away my job on the site. I was anxious all day waiting to see her but tried to keep my expectations low. I figure no one looks as good as their pictures and she would probably be older than she said, and all that. I was wrong.
I was sitting at the bar in a trendy Mediterranean restaurant when she walked it. She told me she would be wearing a pink top and a black flowered skirt. Her hair caught my eye first. It was recently bleached and sparkled an almost white it was such a light blonde. I was able to take her in for a few seconds before she spotted me. Every once in a while you find a person who just looks like a shell of who they are in pictures. She is one of those. Her skin sparkled of health and youth, her features were very crisp, she was taller than I expected do to her sandals that had cork heels and her skirt was made of a very nice silk and hung off her tasty rump in a flattering fashion.
When her eyes met mine I smiled and waved her over. When she got to me she said "you must be Marc!" Her voice was a beautiful soprano and her attitude was bubbly and matched her emails to a T. "Y-y-yyes I am", I stammered, already nervous. Not only was she far more attractive than I was expecting, but she had such a warmth coming off of her. She shook my hand and gave me a peck on the cheek.
I couldn't believe how young she looked. If the bartender hadn't been willing to serve her after checking her ID I would have thought she was 17 at the most. She had a great tan, and her hot pink lipstick matched her top. Her breasts were definitely on the smaller side, but she looked incredibly yummy. She had just been served her martini when the hostess called my name and seated us.
As she was seated across from me I remembered her saying that she had done the "sugar daddy thing before." Who was the crazy idiot who gave this girl up?
To be honest I still didn't believe I would ever have coitus with her, it was too good to be true. Plus my nerves had me jittery as could be. No way this little knockout was going to let my old, soft, self conscious dick darken her pretty pussy, would she? She could aim much higher.
Chloe turned out to be a marvelous conversationalist and she actually was very smart for her age. She was very well read, and I consider myself pretty smart, and she kept up with me every step of the way.
Then she told me she wanted to study abroad in Spain, which I had done and was my favorite foreign country. We talk about that for a long time. Then we discussed movies and tv shows and music and books. We were very similar in our tastes and I began to really want her. I wanted to flat out ask her what it would take to take her home right then. But oddly, I felt like it would be rude to her.
She had been a perfect lady up till then, compared to those other fake bitches, she was a delight, and I felt indebted to her. It was the first time in a long time I felt like any female cared about me, and I really missed that feeling. Despite not having many girlfriends, sparse sex with them, and bad sex at that, the last of those relationships was a decade ago. Sure, I had had sex with some hookers and Asian masseuses, but that sex was always hollow.
Even the sweetest ones, no matter how good their act, didn't really feel real. Yes it was a fuck, but it was no real release. In fact, I had never had an orgasm as good as the first few self gratifying orgasms when I was a kid, I just wasn't one of those types.
Those factors made Chloe even hotter to me. I didn't want to fuck her, I really wanted to make love to her, and my bottom of the barrel scraps of girlfriends couldn't be truly sexy if their life depended on it. Chloe oozed sexiness out of her pores. Her large pink plastic hoop earrings, matching her lips.
The multiple gold and pink bracelets on her right arm knocking together and back and forth with her arm movements. The necklace that looked like a silver string with oversized lime stones scattered around it. It almost looked like some thing from the Flinstons, but was just cute on her. Every thing about her, from her movements, to the constant smile, to the soft feminine voice, the giggle, the flicking of her hair, the flashing of her long eyelashes. I was sad when the waitress brought the check, I was having an amazing time with her.
I sighed and plopped my Amex in the bill holder and signed a nice tip to the waiter. "Oh my gosh, is it really 10:30?" Chloe asked, her surprise seemed genuine. "Yeah, it is. I didn't expect to have so much to talk about," I replied.
"Well shoot. I don't have an early class but I do have a 10:00 one. I should probably get home." Chloe said to me, her constant smile still there. "Oh. uh, yeah ok." I said, the disappointment flooding over me. Maybe she just did her homework to know what to talk about to take up a lot of time and she could bolt with an easy excuse. I wondered if she realized she hadn't asked for the cash.
"So can you give me a ride home?" She asked sweetly. "You didn't drive here?" "No I took Uber. If you were boring I figured I would get drunk." She replied with a giggle. Such a great smile. "Well sure, I would be happy to." We got up from the table and I helped her put her light black cardigan on, though it was very nice outside.
She took my arm as I walked her out to my car, a modest Prius, I loved the mileage. I had to stop my self from spending too much time watching her mid thigh length silk black with red roses skirt jumping out from her butt as she walked. he had just a perfect amount of junk in her trunk. Again I wondered what the hell her last sugar daddy had been thinking. The drive was not far and she lived in a decent little apartment just outside of down town.
The neighborhood wasn't the best but, it also wasn't the worst. "Well Chloe, you were wonderful company tonight. Thank you." "You're not gonna walk me in?" Chloe asked in surprise. "Oh, of course!" I scrammbled out of my seat, fumbling with my belt enough to make Chloe giggle again. I went to her door and opened it and helped her out. She took my arm and I led her to her door. She got out her key and opened the door and grabbed my wrist.
"Come on in, we can have some coffee." Chloe said pulling me into her apartment. Once in the door of the apartment it seemed much nicer than it looked from outside.
Her furnishings were modest, a small HDTV, decent stereo system, a chair and a couch, a small dinette table, a very narrow kitchen, beyond that were two doors. Bathroom and bedroom I would imagine.
Chloe took off her sweater and hung it up. "Take a seat." She said as she poured beans in a grinder. "What?" She said as the grinder finished. "I said why are those framed paintings sitting against the wall?" She had an Ansel Adams, that one with the navy boy dipping his lady in New York and a diner painting.
All in nice frames. "Oh, well I want to hang them but I am a total idiot with tools. The last time I hung something it tore out part of the wall." "Oh you need to use the studs." "The what?" "Do you have any tools?" "Yeah, an old boyfriend left his tools at my place and I have kept them ever since.
There is a ton of stuff in it." She told me. Damn she had nice calves, flexed in the heeled sandals. She was good at doing the lean forward and then up thing to exaggerate her curves. I went to the tool box in the hall closet and found not only a hammer but a stud finder and a little kit full of nails and screws and things.
It took only a few minutes to hang all of her frames, the level making sure they looked right. She came around the corner from the kitchen. "Haha, my neighbors are going to complain about that pounding. . Oh wow! That looks great. Oh my gosh aren't you sweet?" She said in a sigh. She reached up and met me with a hug, forcibly and I fell back a step into the wall next to the frames I had just hung. "Oh. Yo-you're welcome. It was nothing." I held her lightly at her sides.
God her body felt great. Chloe began to pull back and stopped, then got up on her toes in her sandals and gave me a quick two second kiss on the lips, her hands cradling my face. She pulled back, looking me right in the eyes, and blinked her long lashes once slowly.
She giggled and leaned into me again, this time her lips parted when them met mine and her tongue slipped in my mouth. Our tongues tussled as she kissed me long and deep, while she slowly brought her knee up to rub my crotch, feeling my hardening penis in my slacks.
Chloe giggled as she finished our kiss. Without pulling her face back from me she said quietly, "Oh, someone else came to the party. Pleasure to meet youuuuummmm." She said as her lips kissed me again.
She danced in my mouth while her hand replaced her knee in massaging my erection. Of all the women I had dated, of all the women I had paid, I had never felt so turned on before. he was so much sexier than I had felt before. God it almost felt real. After rubbing enough to get some pre cum to make a slight spot on my grey slacks, she smoothly unbuckled my belt and dropped my pants. She continued to rub me through my boxers until two of her fingers slipped inside the front slit and rubbed back and force skin on skin with my penis.
God the bolts of intensity of pleasure it shot through me. I could scarcely believe what was going on, I was drunk with desire for her. Chloe pulled off my lips and kissed down my neck as her knees fell to the floor. On her way down, she yanked my boxers to the floor. I looked down to see her grab my cock lightly with her left hand. Her right hand on her knee. She looked at my almost fully hard penis right at face level and then kissed it right on the tip. She kissed it again but let her lips part just a bit and took the very tip of my manhood in her mouth and flicked it with her tongue.
"O-ohhhhhh-ohhhh-ohhhhhh." I stuttered out, staring at her pleasuring me. She pulled off, looked up and me with those big brown eyes and smiled and giggled. Then she looked back at my unit and began to slowly jack me off as she kissed around it. Each kiss lingering, followed by a few pumps of my cock. Then she cupped the top of my shaft with her hand and held my penis straight while she kissed the under base of my cock. She parted her lips just a bit and stuck her tongue out a pair of centimeters, as rigid as she could make it.
She ran her tongue and lips from my base to my tip, almost causing me to cum in the process. "Mmmm?" Chloe hummed as she looked up at me again.
She kissed my mushroom cap again, then again with her lips parted a smidge, taking just the tip. Then a bit further. Until the whole head of my dick was in her mouth.
"Oh fuck Chloe. Ho-ho holy shiii" I trailed off, my breath escaping me in a gasp when she took me in halfway. As she pulled back, I saw her spit left behind, my cock shining. "Mmmmmmm," Chloe moaned for me as she pulled back to my tip and inhaled me as far as her cute little mouth could. She had most of me inside of her body but the very base was out of her range. "Oh-oo-oo-oo-oo-oo-oo-oooh!" I cried out in a hoarse voice. I saw Chloe look up at me as she pulled back all the way off.
She swallowed, licked her hot pink lips and dove back on my cock, her hand reaching up to my stomach, her fingers splayed. I couldn't believe what I was feeling. The waves of pleasure were picking up power and speed. I could feel my balls tingling. I was almost ashamed to be feeling so much so fast, but her talents and watching her do it was far too much for me. With each back and forth Chloe would vary the pressure of her lips and jaw, keeping me from catching a rhythm.
It simultaneously was helping me hold my orgasm at bay just barely, and also incredibly pleasurable. Chloe continued to moan as she sucked me, giving me the most amazing blow job I had ever had. Not one of those fucking whores had ever done this. "Huuuu. Mmmmmm. Hhhmmmmmph. Ummmph." I was grunting from the effort to keep my cum from heading out. The waves began to radiate in pulses from my testicles, the pair feeling like they were about to clench.
"Mmmmmm? Mmmmm-Hmmmmm!! Mmmm-Hmmmm!!" Chloe moaned in agreement, pistoning on my cock faster and faster. "Oh Chloe!" I panted. "Oh shit!" My head fell back and my eyes closed as I lost my power over my orgasm and felt my balls start to pull to my body.
"Mmmmmmmm!!!" Chloe moaned loudly, still sliding me in and out of her mouth at varying speeds and pressures. "Ohhhhhhhhhhhhhwwwwwww!" I squeaked out as I felt Chloe cup my sack and slide her fingernails lightly along the meridian, just the right amount of pain and pleasure to force the cum to rocket up my cock faster than it ever had. My right hand grabbed the corner of the wall, my left grabbed a handful of her light blonde hair.
The flared and large curled locks waving in response to her movements. She took the first spurt like a champion, she didn't slow her speed or stop the pressure, she kept on chugging, my cum quickly coating my own cock from her mouth and tongue, now slick as oil. Uuuuuuummmmmmmmmmmmmm!" She groaned, and even gave a little giggle. The second shot of cum made my hips buck a bit, driving deep into her mouth, making her grunt for a second but she held her gag reflex and was pushing down on me as that second rope exited.
"Unngh. Unnf. Chloeeeeeuuh.!" I grunted through clenched teeth. The tingling waves of my orgasm washed over me, making my knees jelly. I spurted one more good third spray of my semen and panted, my head against the wall. While that should have been it. Chloe wasn't quite done. She went down on my shaft one more time, as far as she could. Then as she pulled back me pumped a wave pattern from the base of the tongue to the tip, pressing into the base of my cock.
Massaging my base with her rigid tongue waves as she pulled back slowly actually caused me shaft do a post orgasm compression and actually cleaned out the bit of left over cum in my cock and deposited the seed in Chloe's waiting mouth. She finished pulling off and pressed her lips and kissed the tip of my dick one more time. "Hmm-hmm-hmmm." Chloe giggled as she looked up at me, nearly asleep against the wall, my body feeling like liquid magma pleasure.
After a moment I felt Chloe's breath on me. I forced my head off the wall and opened my eyes to see her looking at me. She smiled at me and leaned forward for a long deep kiss. She pulled her lips free, pressed her forehead against mine and whispered, "Can you taste you on me?" I just put my arms around her and held her. She had showed me a pleasure I didn't know existed.
She giggled one more time. "Come'ere. I want to show you my bedroom." I fell in step behind her, watching her ass slither back and forth as she lead me through the bedroom door.