Dolly's Summer Internship
I saw the cutest young spinner type blonde, maybe 20-21 years old, in an elevator today on my way to meet a friend at his office for lunch. No, not that kind of lunch, it wasn’t a Dolly date, but this young hottie was in tight white jeans that stopped at her ankles, sexy closed toe heels, very mature for her age, and a youthful but appropriate blouse considering she was clearly a summer intern running errands for the company on whose floor she got off. No pun intended about her getting off. But what it brought to mind was one of my own summer internships, “back in the day”, as they say. She happened to get off at the same floor as my destination, so watching her young sweet ass a bit longer might be what made my mind linger on her, and think back to my own younger adventures.
Was it sexy or raunchy when my boss, that summer which I’m recalling, told me, “Dolly, you should ALWAYS have a bare midriff, your flat toned abs will get you inside any door you need to get through.” Does your answer to my question change if I told you I was eighteen when that was said to me?
I was slender, lean, fit, in my high school tennis and track body, as I think of it. My "girls" were young and perky, though not quite yet up to their current D cup status. I work hard these days to keep my ass desireable (How’m I doin’ on that, boys? Wink) but at eighteen and playing tennis, these buns were young fresh steel with no extra specific effort. My legs were, as always, tan, fit, though a tad more slender in the quadriceps, but just as defined in the calves. South Florida girls know how to show skin and make men hard. So, what was the answer, was it sexy or creepy of my thirty-one year old boss at the public relations firm to tell me how nice my abs were?
Let’s call him Tim. Which wasn’t his name at all, but since my memory of him includes “first manscaped shaved-pubes man I ever personally got naked with”, I needed something more normal to call him. He was hot, married (though not for long, he was on his way to what became three divorces to date) and he drove a Lamborghini. Maybe the married part would have scared off other girls, but to me that was just a challenge – I wasn’t pursuing him, and I hadn’t taken any vows. Was I really sexy enough in high school to make a hottie in a hot car chase me? Saved me the trouble of chasing him I guess.
So Tim wanted me to be at a big fancy bash on South Beach, lots of important clients and beautiful people, and he told me that the firm had hotel rooms (I won’t divulge which trendy hotel) in case things developed. What sort of things, Tim? Whatever, he told me, with a wink. I frigged myself off in the shower thinking about the possibilities just before I got dressed in a short leather skirt, bare midriff sleeveless blouse (Dolly can follow a man’s directions) and black “come fuck me” spike heels. Black bikini panties. Magenta mani-pedi (I know, cheesy, but I was eighteen and it was Miami).
I flirted, met everyone I was supposed to, enticed everyone to make an appointment to come in and see us, or if they were already clients, to come on back and discuss how else we could help them get to where they wanted to be. Nice little double entendre. I had many arms draped around my shoulders, way more touching than was appropriate, and I lost count of how many pairs of eyes looked down my blouse. Tim was smiling, pleased, and when things were finally winding down at 3:00 a.m., he said, “I’d offer you a cab home but as hard as you worked why don’t you use one of our suites. It's okay for you to be out, isn’t it?”
This wasn't my first time not to make it home. I’d spent the night out before. And I figured my parents wouldn't be too worried. My father knew the owner of the firm – which was how I got the interview (I got the JOB on my merits, thank you.) Really, by the end of the summer, when Tim’s wife had moved out and he and I ended up having hot sex at lunch time in his high rise condo, he told me that yes, I was sexy, but if I’d been stupid or couldn’t do the job, they never would have hired me. He pointed out how much client contact they gave me even though I was eighteen. How sweet that he sucked my nipple before saying, “if you were simply sexy, we’d just have brought you back and wasted your time with a second interview and tried to see if you might have gone down on us with your talented mouth. You’re sexy AND talented.” I blushed, then sucked his cock until he burst onto my tits. “God are you talented,” he sighed.
But that was later, at the end of the summer (did I spoil the ending? Sorry. Some of my friends complain some of my blogs are too long. So I thought I’d let you know a bit about how it all turned out sooner, rather than later). Back to South Beach client and prospect night, I took the key (remember when hotels used actual keys? ) and thanked Tim, then reached up to the back of my neck and tried to crack my own neck, exhaled and said it had been exhausting, but fun. “You did a great job, you deserve to relax and tomorrow you are taking the day off. My orders – sleep in late, order room service, go to the spa, charge it all to the room. But the spa is closed this time of night of course, so I guess I need to give you a neck rub.” I gave him my Dolly grin. Handed him the key back, and told him I’d take him up on that. “Lead on, Tim.” We went to the suite, overlooking the waterway, and what do you know, there was champagne. He opened the bottle, I collapsed into an oversized comfy chair near the glass wall overlooking the lights of the city, sipping champagne, and he stood behind me. God I was so wet in anticipation of this older gorgeous man taking me.
“You’re too tense. You need to relax, this should help.”
He lectured me as his fingers massaged the tension from my shoulders. I smiled. I hadn’t realized how great Tim’s hands were. I knew he was hot, and we’d been working together for a while but nothing more than the flirting until that day. As his fingers moved over my shoulders and arms, I felt a stirring of arousal. I also should mention that with all the time I was putting into the internship, I hadn’t been laid in more than three weeks. With my eyes closed, I felt myself relaxing. I also felt Tim’s fingers slide inside the neck of my blouse to rub my bare shoulders. Laughingly he commented about the lack of bra straps on my shoulders.
“Strapless. More comfortable.”
I reached up and unbuttoned another button on my blouse to give him more room to work with. Subconsciously, I probably did it so Tim could have a better look down my blouse. Okay, consciously. Tim’s fingers were amazing. His touch was firm but not rough. The tips of his fingers were moving lower and lower, stroking down my lower neck. I think we both knew how this was going to end, but that didn’t make it any less exciting. I could hear Tim’s breathing getting a little more unsteady and rapid. My panties were already soaking. I unbuttoned another button. There were only three buttons left on my blouse.
Tim’s hands started to move down lower but he stopped, hesitated. Reaching up, I covered his hands with mine and moved them down. His finger tips rested on the top of my breasts.
“I didn’t come in here to take advantage of you. I came in to help you relax.”
“What if I wanted you to take advantage of me, Tim? But yes, I do need to relax.”
Unbuttoning the rest of my blouse, I said lucky for him I need a lot of relaxing. Spreading my blouse open, I game Tim a good look from above of my white strapless bra, barely holding my C-cup breasts. My nipples were hard, pushing against the satin. Tim’s fingers continued their massage over my neck and shoulders and then down to cup my breasts through my bra. I shivered when he slowly pushed his fingers down inside my cups, stroking my nipples. My with eyes closed again, I concentrated on how his fingers felt. The tips were a little rough as they moved up and down over my nipples. My nubs were hard, elongated. He pulled and pinched each one. When he withdrew his hands, I shivered.
Tim moved around in front of me, standing in front of the window. Reaching behind me, I unhooked my bra and tossed it on the floor. His hands reached down to cover my breasts again as he knelt in front of me. When his mouth closed over my nipple, I nearly came. Tim wrapped his lips tight around my right nipple and sucked, pulling my nub into his warm mouth. The suite echoed with the sounds of his sucking. As his mouth tortured my tit, his other hand was stroking my left breast. Pushing it up and then releasing it, he squeezed my flesh over and over again. I was moaning. Tim moved his mouth to my other breast, sucking it hard and fast. His hand dropped down and rested on my thigh. Sliding his hand up under my skirt, he moved past my garter and straight for my pussy. When his finger moved up and down over my panties, I nearly shot out of my chair.
Tim’s mouth never left my nipple as his fingers pushed against my skimpy black bikini panties, rubbing my pussy through them. I was soaking wet. I tried to spread my legs wider but was restricted by Tim and the chair. His finger slipped inside the side of my panties and slid over my wet lips. Moaning, I pushed out at him. It was exquisite torture as the tip of his finger parted my fold and slipped inside my pussy. Slowly, he fingered me, slipping and sliding his finger in and out of my hole. I was moaning. His mouth sucked my other nipple again as he withdrew his finger. When he slid three fingers inside me, I groaned. Twisting his fingers in and out, my pussy clenched and unclenched around him. I felt my orgasm and grasped his arms, digging my nails into his strong forearms. Moaning, I pushed out and came on his fingers.
Withdrawing his fingers, Tim brought them to his mouth. I watched as he licked and sucked my juices from his amazing fingers. He stood and tried to back away. Reaching out, I grabbed his belt and pulled him towards me. Rubbing my hand up and down his huge bulge, I felt how hard he was. And boy was he a rock! Undoing his pants quickly, I reached in and took his cock in my hand. He was average length but thick. Tim groaned as I slid my hand down his shaft, twisting slightly as I did. The tip of his cock was almost purple as I flicked my tongue across it. I tasted his flavor and moaned. Wrapping my lips around his cock, I sucked slowly. Pushing my mouth down, I twisted my fingers to the base of his cock and then followed my mouth back up. Over and over again, I sucked Tim’s cock, wrapping my lips tighter and tighter around him.
Releasing Tim from my mouth, I held his cock in my hand. Licking the underside, I enjoyed Tim’s shaft as if it was a lollipop. Mmm yummy! Spitting on the tip, I pushed my hand down his shaft again, pumping him. Tim was moaning, pushing his cock into my hands. Leaning down, I pulled his balls into my mouth and sucked. I felt his cock stiffen even harder in my hand. When he started to moan that he was going to cum, I took his cock back in my mouth. I sucked fast and hard, pulling my mouth up and down his cock. Tim moaned and pushed deeper. His cock exploded in my mouth, filling my mouth with his cum. I kept sucking and stroking, swallowing every last drop like a good girl. Yeah right, like I’d ever been a good girl!
Licking my lips, I stood up. Tim reached around me and unzipped my skirt. Pushing my chair out of the way, Tim leaned me up against the desk. Tearing my panties down, he tossed them to the side. I was naked except for my heels. Tim sat me on the edge of my desk. Opening my legs, he stroked my pussy with his fingertips. He smiled and then knelt down in front of me again. This time, it wasn’t his fingers on my pussy. It was his tongue.
I nearly exploded when the tip of his tongue flicked across me. With slow, languid licks, Tim tortured me. His tongue covered my pussy, licking upwards to flick across my clit. Using his fingers to open me wide, he pushed his tongue inside me, slowing inserting and withdrawing the tip of his tongue. I was moaning, rubbing my own tits, begging him to eat me, fucking eat me Tim, oh shit Tim… wow, I still get worked up thinking about that night. His mouth covered my pussy, sucking my lips into his mouth. Then, he released me again and went back to licking. Over and over again, he changed actions. I was begging to be fucked. Begging to cum. Tim rubbed just the tip of his finger over the bottom of my pussy as his tongue worked over my clit. My pussy tingled, my orgasm was building. As he pulled my clit into his mouth, sucking hard, and his finger slipped inside me, I came hard, moaning and twisting on my desk.
Without saying a word, Tim stood, opened my legs wider and then retrieved a condom from the trousers I’d taken off him. I felt a little disappointed not to feel flesh on flesh, flesh IN flesh, but I was young and thank goodness he was responsible (while being irresponsible enough to fuck his eighteen year old intern). Tim unrolled the condom on his thick tool and rammed his hard again cock deep inside me. I fell back on my desk and begged him to fuck me harder. Tim lifted my legs up over his shoulders, pulling my ass up off the desk, and slammed his cock over and over into me. I came again quickly. Pulling out, Tim lifted me off the desk and turned me over. Setting one knee in my chair, he opened me wide and slid his cock back inside me from behind. I love doggy-style. Tim’s cock filled my pussy as he slammed again and again into me. I grabbed the edge of the desk and looked up. Oh my god! I was in heaven with this hot older lover initiating me into lust (okay – maybe I wasn’t being initiated exactly, but it was my first office affair. At least, I think it was. Not that I’m going to publish very much about the fun I had under the age of eighteen. Other than to say, no, when I turned eighteen, I wasn’t a virgin.).
I moaned louder as Tim drilled my pussy. Reaching down, I grabbed one of my tits, squeezing it. I looked up and watched Tim pump away and work my body, bending me however he needed, enjoying the slender eighteen year old version of Dolly. His huge hard on lasted so much longer than high school, or even college boys. He didn’t take it out. He just stood and fucked me like I wanted him to. Tim was moaning, ramming his cock harder and harder into me. He pulled out all the way and dropped down to run his tongue over my pussy again. I moaned and pushed back against him. Rising, he slammed his cock into me again. His hands were around my waist, holding me. I felt another orgasm. I looked up at Tim and that intensified how hard I came watching him. He wasn’t in love with me. But there was something so …primal. That was the hardest I’d ever cum up to that point in my life. Tim wasn’t far behind. His cock filled the condom while deep in my pussy. Pulling out, he again dropped down behind me, licking me. I’d never had a man lick my pussy after his cock had just been inside me.
I was moaning, thrusting my pussy into his face. When I came again quickly, I pulled his head back.
Turning around with my back to him, I reached down and grabbed hold of his amazingly still hard cock. Slowly, I guided his cock up into my waiting pussy. This time he didn’t have a condom close at hand. “Are you clean?” I asked him. Nowadays, this would never do. So I am lucky to have survived my teenaged sex years without ever having contracted anything or getting knocked up. “Yes, always.” Though I now fully declare this behavior to be in the “Don’t try this at home” category, all I knew that night was I wanted more, my boss said he was clean, and I knew I was on the pill.
As I lowered myself, sitting in reverse on his lap, Tim moaned and grabbed my hips. Pulling me down onto him, his cock filled my pussy. Bracing myself on the chair's arms, I slowly started to fuck Tim. His hands helped me, raising and lowering me onto his cock. We both moaned and grunted. I wasn't sure what kind of stamina he was going to have, since he’d just cum. I was in for a definite surprise.
Tim reached around me with one hand and found my hard clit. Pushing his finger against it, he fingered me as he fucked me. I was bouncing up and down, begging for him to fuck me harder. Yeah, now that we were fucking a second time, all bets were off and I was talking dirty! I couldn't believe I was cumming again. Tim reached up, grabbed my tits in his hands and held me still as my orgasm subsided. His cock was buried deep inside my tight pussy. He stayed perfectly still.
After a couple of minutes, when my body had stopped shaking, Tim lifted me up and off his cock. Turning me around to face him, he thrust two fingers deep inside my pussy. I grabbed hold of his shoulders, bracing myself as his finger drove deeper and deeper inside me. I felt yet another orgasm begin and push over me. Tim looked up and told me to suck him again. I loved that he didn’t ask – it was a command! Dropping to my knees, I took his cock, now wet with my cum, in my mouth. I sucked hard as he thrust his cock deeper and deeper into my mouth. I licked his balls. I sucked his cock. I stroked his shaft. Over and over again, I fucked him with my mouth. He still hadn't cum a second time.
Pulling my mouth off his cock, Tim told me to stand up. I did and waited. Tim smiled. He told me to lay over his desk with my ass in the air. He wanted to fuck me the way he'd fucked me before, from behind. He told me he loved the sight of my tight young ass when he fucked me. Married men say the sweetest things.
Bending over the desk again, I spread my legs and begged him to fuck me. Not that he’d needed the invitation. Tim guided his cock to my pussy and then stopped. I could just barely feel the tip of his cock against my pussy. He slowly, pushed just the tip inside and then pulled out. He did this five or six times before he finally plunged all the way in my pussy. He moaned out how tight my pussy was as he fucked me. His hands grabbed my waist, holding me and pulling me back to him. With each thrust, he was drilling me deeper and deeper with his cock. I was moaning, telling him how good his cock felt, to fuck me harder. Tim did, fucking me till his balls were slamming against me.
Reaching down underneath me, Tim ran his fingers over my pussy. Slipping them inside next to his cock, he stretched me wider. I came hard on his cock and his fingers. Pulling his fingers free, I expected him to lick them clean. Wrong. I shivered when I felt his wet fingers at my asshole. The tip of his finger slid slowly inside me, stretching me. I knew what was coming next and I braced myself. Tim withdrew his cock from my pussy and pointed it at my tight asshole. As he slowly pushed against me, my phone rang.
I reached up, trying to sound normal, and answered my phone. My parents! I explained that the party ran long, that the company was worried about me taking a cab so late, reminded them I’d mentioned that we might stay overnight. (I hadn’t, but since they only half-listened to the eighteen year old version of me, I figured they’d believe that I had told them and assume they’d forgotten.) I told them that my boss and his wife had checked me in. I knew the part about his wife would reassure my mother, and apologized that I hadn’t called but it had been so late. Tim at least slowed his fucking from slamming to twitching while I spoke to my mother. But I gasped. What’s wrong dear, she asked. Bumped into something, I hadn’t turned the light on yet when you called. Mom told me to be careful and she’d see me in the morning, Might have been the first time I ever told one person I loved that person while another person was fucking me. Wouldn’t be the last. Still love you, by the way, Mom.
Tim rammed his cock into my tight ass, filling me full. He laughed at my call and fucked me harder. Reaching down, he fingered my pussy as his cock drilled my ass. I felt a continuous roll of orgasms wash over me. I'd never cum so hard or so much in one day. Tim continued to fuck me, pounding his cock in my ass. His fingers spread my pussy as he rubbed my clit. I was groaning, begging for him to cum inside me. I’d never had a bare one in my back porch before Tim. Love, exciting and new – NOT!
With a hard thrust, Tim grunted and filled my ass. Pulling out, his warm cum shot over my ass. I was breathing hard, totally and completely satiated. Tim sat back in the desk chair, his cock still dripping. I stood. Pulling me back against him, Tim slowly licked my ass clean. Damn, another new boundary crossed for me that night. I moaned as his tongue wiped across my ass. As I made my way to the bathroom and tried to clean myself up a bit below the waist, Tim got himself back into his pants. No washcloth. How raw! I smiled.
"I’m going to let you get some sleep, you seem relaxed now; you’re much less tense. Like I said sleep in, treat yourself to whatever, and no need to come in until you’re ready. I think the best way to deal with this little situation is for you and I to sit down and discuss it only away from the office, don’t you think? How about tomorrow night, right back here, seven o’clock, we’ll make an early night of it so you won’t have to lie to your parents again."
I smiled, got up on my tiptoes and kissed his lips. We hadn’t kissed with tongues yet, and didn’t at this point, either. He’d been the best fuck of my then young life. I walked him towards the door. Just as I opened it, Tim had one last comment. "No panties."
Ah, I wonder how that cute spinner of an intern’s summer is going? And the funny thing is, Tim’s at a new firm all these years later. And that’s who I was going to visit for lunch. We’d stopped fucking after a few weekend get-togethers after the summer ended, when he was in the process of his first divorce and I was onto my college romances and sexual adventures. But we’d always stayed friends, and he had even encouraged me to be an escort as his form of compliment to how I keep myself in shape. If only he knew. But then, Tim might not be my target client in the hobby, he seems to still like them young. When Tim’s secretary led me into his office a few moments later, I saw the intern walking away from his office, her eyes wild with anticipation. Some men never change!
Purely fictional fantasy for your reading pleasure!