Summer Job. Small World.
I was working a summer job with a major marketing company when I was an MBA student when one of my fellow summer interns, Nancy, asked me to be "chaperone" of sorts on a double date. Seems one of the brand managers had just separated from his wife of less than one year and less than two weeks later had asked her out on a date.
Hello! Can you say sexual harassment? Hostile work environment?
But Jim was cute in a "I wanna get laid but you don't have to worry, I'm cuddly not dangerous, so I'll keep trying but no force or coercion will ever be part of my tactics while trying to get into your panties" kind of a way. You know the type. Mother's love these guys, they are charming and funny and have dimples at the door. 5'9" so they look harmless when they pick you up and your daddy meets him and thinks, "Geez, does this guy really have what it takes to keep up with my daughter? She's too much for him..."
Okay-- that last part, yes, that's what my father must have thought sometimes. I developed early, got started early, and, ahem, didn't initially realize how vocal a lover I was or how sound carried in my parents' house or at our vacation home or on a yacht. So poor Daddy heard way more of his daughter's recreational sex life than any father should have to until one day Mom took me shopping and in the car said to me, "Dear, it’s not a good idea for you to have sex if your father and I are in the same place as you. Don't be upset, we don't mean to spoil your fun or to imply you're doing anything wrong and we trust you're being safe, but we think you're not aware that we can hear far more than you might suspect."
My response was , "Huh? Like what do you hear?"
Mom turned to me with a "Really?" expression on her face and simply said, "Everything, Dolly. If I didn't know it was you I'd think your brother needed to turn the volume down on his porn. You do so well in school, you're a champion athlete, you're beautiful, I guess we shouldn't be surprised that you'd be world class in sex, too, but please dear, unlike your report cards, medals, and pageant results, this is not an area of your talents that your parents want to hear about."
Not sure I've ever been so embarrassed.
But mom was cool and followed up with, "let's get you some heels and maybe some lingerie while we're shopping; just because we don't want to hear it doesn't mean your loving mother isn't thrilled for her daughter to enjoy life so much. Just please, dear, somewhere else, a closed door doesn't do it."
Note to gentlemen: Hotel doors, being required to meet fire codes greater than residential doors, muffle the sound much more. Go ahead, make me howl, we're safe at any incall where I host."
So where was I? Oh yes, cute newly separated Jim and Nancy were going to go out on a date and she wanted protection from him trying anything so I was her choice for a double date. But I didn't know anyone in the city where I was working that summer. Hey, it was early summer. By August, (ah, smiling!) yes, I knew lots of men in that town. *Wink.
"That's the easy part, Dolly," Nancy told me. 'Jim's college buddy is coming out to visit him and he can be your date. You can both keep Jim in check."
Nancy, Nancy, Nancy. Why go out with a fellow if you want him kept in check? Like I said, Jim was cuddly, harmless and cute. I had him pegged for a premature ejaculator if he'd been with me. I think I was far more aggressive than he was used to. But I wasn't the one going on the date with Jim, Nancy was. Nancy was five foot five, about one twenty, a C-cup brunette with some natural auburn to her hair, and blue eyes. More tushy than I'll bet she wished, and fair complexion. A seven. Pretty, but not a head turner, no one ever walked into a wall or drove into a fire hydrant because their head was turned to view her.
I was wearing a pair of white capris and a colorful blouse with a scoop neck, tight to show off my curves, with some sandals to show off a new hot magenta pedicure, and Nancy was in a red fuck me summer dress when the boys picked us up. Jim was in blue jeans and a polo shirt, and since I also knew Jim from work he said, Dolly, this is my friend Rich."
Rich was wearing a big smile. I was wearing a look of shock, I suppose.
We'd gone to high school together. Several states away from where we stood, about to embark on a blind date. He was two grades ahead of me. He'd been the captain of the baseball team and was recruited to play at a big time college baseball program, while I was a ranked junior tennis player and then tried to tour a bit before college and business school followed when I realized I wasn't going to become #1 and I'd gotten about as much out of tennis as I would. So I hadn't seen Rich in a number of years. I didn't know if he'd recognized me.
"Dolly, " he said, eyeing me up and down before thankfully returning his eyes to mine, "you might not remember me, but we actually went to high school together. Small freaking world. Didn't you go play Wimbeldon? When Jim told me I'd be double dating with him and told me your name, I thought, "No, it can't be her, what are the odds?' but here you are."
"Oh my God, Rich, I totally remember you, How the hell are you, you dated Clarissa Golden when you were a senior, she was my tennis team captain!"
Now, Clarissa was team captain because she was a senior. I was far and away the #1 player on the team, but seniority was very important in high school. Clarissa was also bi-curious and we did some hot and luscious making out at Friday night parties when I'd get invited along with the seniors during my non-tournament weeks. Having a hot body scored me a lot of invites, and Greg Kirkland had dated Clarissa the semester before and I hooked up with him at a party and then later commented to her, "did you think he was a slobbery kisser? That boy needs a kissing lesson." Clarissa laughed, hugged me, whispered, "but he had that nice fat cock, it took a couple condoms before he could get the thing to go on without struggling so much he lost his boner,"
I laughed and had to speak into her ear to be heard at the party, just like she'd spoken into mine. Whatever perfume she wore, Oh My God, it should have been called, "Lesbian Seduction" because I just spontaneously kissed her neck after I said, "I know, my jaw is still sore for sucking him." And I felt Clarissa embrace me, dig her nails into me and moan. She nipped at my ear and said, "who needs Greg, come with me, let's take a walk."
Mouths did not meet pussies that night, but fingers did. Not my last night with Clarissa. Who at the time was dating Rich, so I was staying away when they were together because I just didn't want to cause a scene.
"No, I haven't said anything to Rich. I like boys, but you're too hot to resist and there's something so erotic about being with a sexy girl like you, Dolly, feels so naughty, like I'm corrupting you," she told me another night when she and I made out and sucked each other's nipples in a car. "I think he'd freak out. You're just so cool with this." Then we kissed some more.
Returning to my then-present, my blind double date with Rich, I wondered, what did he remember, other than tennis.
"And yes, I played Wimbeldon. My best was a quarterfinal. Got blitzed one and one by a Williams sister."
He laughed. "No shame in that. Which one?"
"Didn't matter. That was the third year in a row one of those girls crushed me at a major. There were TWO of them. I realized the quarters was about as far as I was going to make it on tour, and having gotten there, I decided it was time to retire and go on to something else. I went to college as a twenty-three year old freshman. Lived off campus, so my experience was different, but now in business school I feel much more ready than many of my classmates since I'd been around the world and managed my career. The tennis tour had been my business for five years."
Rich took my hand in his, and I just naturally interwove my fingers with his. I did some math. So I'd made it through college in three years, now a year of MBA school, I was late twenties, and he was close to thirty. We walked a few steps to catch up with Jim and Nancy, who'd headed on foot toward the chic bistro where we were having dinner."
"So, Jim and Nancy, they need a chaperone? What do you know, all I know is that he just got separated and makes excuses to come by our department, what's the scoop on your buddy?" I asked. Could Rich tell I was really asking if he and I needed a chaperone?
"Remember Virginia Merrill from high school? Nancy is sort of like her." Rich said. This familiarity thing was just blowing my mind. Yes, I knew exactly who he was talking about. "Virginia the Vestal Virgin? Biggest cock tease in the county! Oh my God, is that what Jim told you Nancy is like? Why would he go out with her if he thought she was just a tease?"
"Well let me turn it around, Miss U.S. Open, what do YOU know about your friend Nancy?"
"She's gorgeous, a spoiled daddy's girl, and hasn't gotten laid so far this summer, best as I can tell, because we're splitting a sub-let."
His eyes got wide. "Splitting a sub-let? So you've seen her in the nude, like when you shower?"
I rolled my eyes. "You went right there, didn't stop to pass "Go" or collect $200, straight to naked women in the shower?" I shook my head. "What am I going to do with you?"
Now truth be told, I had seen Nancy nude, she wasn't into any experimentation (a pity, she was really pretty and immaculately groomed, spent way too long in front of a mirror and only stole a couple glances at me, probably comparing boobs--a competition I won!). And I was getting a little moist in the kitty all this innuendo and flirting.
"I know one thing you can do with me..." I trailed off as I took his chin in my hand and kissed him, softer, and then as he held the kiss and I sensed he wanted me to lead, I offered my tongue, which his mouth accepted, and soon we were just plain making out.
The forced, fake coughing from Nancy broke the mood. "Our table's ready. Put your tongues back in your own mouths and let’s go eat." Nancy was so prissy. So, what did Jim want with her again? And damn if I didn't suddenly realize why Rich's kiss was so nice. Clarissa! My God, he kissed just like Clarissa! Or more accurately, just like someone kissing Clarissa ends up kissing, since Clarissa took charge. I'd been sort of imitating Clarissa ever since, and Rich was kissing like I did when I'd have some girl on girl make-out time with Rich's high school girlfriend (who again, was my high school bisexual same sex hook-up for a while during the same time as they were dating.)
And suddenly I wondered...had I ever tasted Rich's seed from Clarissa's pussy? There were a couple times she claimed she'd been exercising but there was something more than just cardio modifying her body those times.
We managed to get through dinner. I think I had fish. There was definitely a salad. And mixed drinks which I usually don't do, but everyone else was.
Not so naughty Nancy suggested we go back to our sublet. Hurray! I can get laid, I thought. Not so much. The lights were too bright, the mood was not there. They were at opposing ends of a couch tossing a remote back and forth, though eventually her feet ended up in his lap and he gave her a foot rub. That's not a foot fetish thing, if it’s just the rub.
I asked Rich if he wanted to see the city views from my bedroom balcony. I thought the daggers from Nancy's eyes would go right through me. I no longer cared, Nancy didn't need a protector, she needed a good fucking. Not that she'd admit that. Whereas I made no secret about wanting to be fucked.
I stepped behind Rich and wrapped one arm half way around the waist, the other hand I moved up from under his crotch and cupped his thing. Oh God yes, nice and fat like Clarissa had said. Yes, I'd masturbated to thoughts of Rich back in the day while using a big sized vibrator. I was going to ride this ride, I was definitely old enough to ride it now.
Rich spun me around, and kissed me, stronger this time, which I liked, and I moved from cupping the entire package to grasping his shaft, and then undid his belt, trouser button and lowered the fly to release that trouser snake. Big fucking snake. Already with a healthy dollop of prelube oozing. Oh he wasn't going to last.
An inner smile. A fast cummer means the second one will last. Or at least that's the broad generalization.
I was on my knees and Rich was stripping and I moaned onto his hot, hard manhood. Tongue-bathed him. His hands held my head, then he was taking off his shirt, shimmying out of his pants. I had all sorts of precum smeared around my lips and mouth, and Rich lifted me up by the shoulders and said, "fucking kiss me with that mouth, you feel so good Dolly." And then again, flashback to Clarissa as his kissed seemed to be licking his own flavor off me very deliberately, just like Clarissa used to do after I went down and feasted on her sexy pussy. Skills that I developed with her helped me cure the boredom on the tour a couple times. Wouldn't you love to know which players I tasted and pleasured? *Wink.
Rich had his fingers in my crease and then he was stripping me and it dawned on me that my door wasn't fully shut, like I gave a damn at that moment, hell, what was my downside, Nancy the tease might surrender to her urges and join us? (Wish that it could have happened that way, but alas, no.)
Rich was good with his fingers, and where he was missing the strike zone I reached down and re-targeted him. The first time I did that he broke that full mouth deep French kiss we were sharing and smirked, whispering, "nice, yeah, show me, that's hot" and I knew he wasn't going to be intimidated. Clarissa had taught him well, that sexy slut was take charge and he'd learned as a high schooler not to let his manhood be intimidated by a woman showing him what she wanted or taking the lead.
Guys, are you taking notes? Seriously, you book dates with Dolly Jewel and then some of you try to control me and get pissed if I go wild? Most guys know and understand how good it’s all going to be if I get my sexual way, but a few guys have had fragile egos, and I can let the man lead....but it’s so much better when I lead! But back to Rich who had me naked and was over me on all fours while I was on my back, and he was moving south on my body.
Nice tongue. Oh Gaaaawwwdd, nice fucking tongue! Usually the big cocked guys are one trick ponies and never had to develop other skills. Rich had a big dick and could still rub, flick, tug, tingle, tease, lick, suck, and everything else pleasant a boy does to a girl with hand and mouth as foreplay. Suddenly two fingers ventured into my very wet sexual landing cave and twisted up in a "come hither" motion and pushed me over orgasm cliff for the first time that night. I went cliff diving again not maybe two minutes later. Pretty sure I didn't stop convulsing in between. I begging him to spin around. "I need your fucking cock in my mouth, Rich, that big meaty dick, want me to suck it, swallow your cum?"
What a pair of chaperones, right?
Yes, found out the next day that Jim and Nancy watched, which got Jim hard, and he tried to grope Nancy and she cock-blocked him, with "not on a first date."
Again, so WHY was she out with this guy freshly separated from his wife? I've been the rebound girl, the first "new" pussy for a newly separated guy. Sort of like volunteering for the red cross, such a humanitarian thing to do, appreciated by the recipient on fundamental levels.
Jim ended up cumming in his pants, I learned, from a hand job through the pants (her hand outside the fabric) from Miss Tease, and for her that was giving in. They were watching me reverse cowgirl ride Rich's cock, which was straining under the magnum I had in the night stand. Where's a “Magnum Ecstasy” when you need one? He filled that condom while I was bent over the foot of the bed and he stood behind me, his Coke can cock buried in my womanhood, and later I titty-fucked and sucked him and he came on my chest. Nancy? No orgasms that night.
We hadn't even dozed off, but it was all of the sudden six a.m., and Rich and I showered together, passionately but we didn't out and out fuck, though we did kiss and fondle in the shower.
We made a sort of towel talk, you know, if we'd been in bed it would have been pillow talk, but there we were, intimately toweling each other off. We agreed to date again when the summer job ended and I'd be back at school and a heck of a lot closer, it turned out, to where he was working. I had a year left of business school. The fire was never the same, and after three dates we went from naming our children (part of his attempts to get me to let him fuck me bareback was to talk romantically about the stories we'd tell our children and who'd perform the ceremony and where we'd have the reception) to sharing intimate details of our prior sexploits with others, to just plain silence as we'd run out of stuff to say other than, "God that feels so good."
The magic had passed. Jim and Nancy? She told him they were better off as "friends" which was hilarious since the summer ended and they never saw each other again. Lost track of her after school. Tried Googling her, but she must have gotten married to someone with a common last name because I can't find anything about her on the internet.
And the final farewell from Rich was just that vague, "I'll call you when I know what my schedule looks like", a call that was never made.
But the call I did make was to Clarissa. Married, trophy wife, country club, two designer kids, Mercedes SUV, husband about a dozen years older than her, a dog from a breeder with AKC papers, mani pedi to die for, had gotten her tits worked on (ahem, what, like I'm going to criticize THAT? *wink!) and everything a golden girl could want. Except...
Except a muff buddy to scratch her Bisexual-itch with. We met for wine. My friend the concierge had booked me the presidential suite of a certain ultra chic Miami hotel for ridiculously cheap money (no one's using it, Dolly, and I'd still like to have a second go-round with you like the time you and that other tennis player came here during the Pro Open in Key Biscayne and you included me in an impromptu three-some, hottest night of my life." To which I was thrilled because meeting a straight concierge was like a needle in a haystack. I loved showing Clarissa how I'd matured as a lover over the years, and she had a few years of pent up pussy-desire, and she wore her huge diamonds and it was such fun to seduce a married loving wife to be my lesbian lover. We laid there after our third orgasms, perspiring bodies, hers still firm from yoga and pilates, and me, well I'm always in the gym, and we were panting, embracing, and she buried her face in my neck, her soft amazing lips on my throat, and Clarissa inhaled and said, "you still smell the same." I smiled and hugged her tight.
The she surprised me and said, "you'll never guess who called me, out of the blue, I wonder if you'll remember him. Do you remember Rich? I dated him in high school back around the time you and I first hooked up. I wonder how he's doing...."
I was about to tell her but then Clarissa guided my mouth to her nipple and I licked and played with her body, reveling in the reunion sex we were sharing.
Purely fictional fantasy for your readimng pleasure!