I guess every boss who has an attractive secretary has at one time or another fantasized about having sex with her. I know I certainly fantasized a lot about Lilian, who had been my secretary for about 2 years. She is a very attractive sultry Venezuelan, about 5’4″, with long dark hair and a lovely voluptuous figure, perhaps slightly overweight, but in a very sexy way. We had a great relationship at work and I’d even been out for drinks with her a couple of times, although nothing happened except that I would get home and masturbate while fantasizing about her.
About two months ago, we finally got a chance to travel together to an island in the Caribbean where a conference was being held. At the time, Lilian was nearly five months pregnant, although it didn’t prevent her from travelling. In fact, she thought it was a great opportunity. The resort we were going to stay in was one of those really classy, expensive ones, all paid for and we found that we had been given adjacent rooms on the beach side of the resort. We seemed to have plenty of free time during the conference and spent quite a lot of time socialising together over the first few days. By the weekend, we were very good friends and had got quite used to slipping in and out of each other’s rooms. As often as not, I’d be in my shorts when she walked in and I’d gotten used to seeing her look approvingly over my torso and occasionally eye my groin. After several days away from home, I’d begun to wonder what it would be like to have sex with her.
On the Saturday evening, we decided to have dinner together at the resort restaurant. I dressed and then dropped in to pick up Lilian. She had just about finshed dressing, wearing a very attractive black dress with a plunging neckline, and with her thick black hair tied up.
“Hi, just let me finish putting some make-up on.” she greeted me.
“You look great already.” I smiled, watching as she slipped on a pair of shoes and then applied some deep red lipstick. She did in fact look amazingly sexy and I felt a slight stirring in my cock as I glanced at her freckled cleavage. God, I needed a fuck badly, and if Lilian didn’t oblige I was going pussy-hunting tonight.
Dinner was pleasant and we got on really well. Of course, Lilian wasn’t drinking, but I had a couple of glasses of wine and then we watched a little of the cabaret show before heading back to the room. The disco had started and I was planning to head that way later to see if there was any nice pussy to be picked up. Back in Lilian’s room, we sat on her huge bed and chatted for a while over a coke. I said I would soon let her rest while I went to check out the disco.
“Hmmm…I noticed you checking out some of those Caribbean chicks.” she laughed.
“Was it that obvious?” I protested.
“I’d say it was. You couldn’t keep your eyes of one of them.”
I laughed ruefully, “Well, I can’t deny it. It’s not easy being in a resort with a beautiful woman but in a separate room. I guess I’m just getting horny.”
“Since I got pregnant, I’ve been horny all the time.” she giggled.
“It’s normal.” I smiled. “Anyway, it’s easy enough to take care of, isn’t it? I bet your husband likes it.”
“Oh he does, but he’s not here right now, is he?”
“Hmmm .. that’s true,” I said, playfully, “there’s always masturbation, though.”
“Oh yes … but it’s not quite the same thing though. Not the same as a good stiff cock.”
By now I was totally aroused and so replied, “Well there’s one of those right here in this room.”
She moved her face a little closer to mine. I could feel the warmth of her breath as she whispered in a sultry voice, “So why don’t we make good use of it, then?”
Instinctively, we kissed. A hard, deep, passionate kiss, her tongue probing my mouth. I responded likewise, pulling her into my arms and feeling the warmth of her body against mine.
“Are you sure about this?” I asked.
“Oh yes.” she replied. “Just for tonight. I need it as much as you do.”
We kissed again. This time, as I kissed her sweet-scented neck, I ran my hands over her firm, warm breasts. She responded with passionate kisses, harder and harder.
“Would you undress me, please?” she sighed.
I helped her stand and, turning her back to me, unzipped her dress, then slowly slid it off her shoulders and down to the floor. Underneath, she wore a black bra and panties. I unclasped her bra and then running my hands over her shoulders, gently slid it off, so that now my hands were cupping her heavy breasts, her head pressed back against me and my fully aroused cock pressing into her buttocks. I felt her nipples swell against the palms of my hands. Her breasts, normally a 38C, were already larger than usual, and her nipples were now huge and dark from her pregnancy. At least three inches in diameter, they must have been at least an inch long now as I continued to tease them between my fingertips.
Continuing to play with one nipple, I slowly ran my hand down over her swelling belly and under the waistband of her panties. I felt the coarse thickness of her pubic hair as my hand probed deeper. She was already wet and began to writhe against me as I located the outer lips of her pussy. I withdrew my hand and, nibbling at her neck, presented my fingers to her lips. Sensuously, she drew my fingers into her mouth, sucking her scent off them. I slid her panties down over her full hips and allowed them to drop to the floor. She was naked. I turned her around and guided her back down on to the bed.
She spread her legs a little, drawing one knee up and let one hand stray down to the thick triangle of black hair between her legs while the other stroked her breast. “Now you get undressed.” she smiled. Standing in front of her, I stripped down to my boxers. Then, all the time looking at her, I slowly lifted them off my throbbing erection, which was now just about as hard as it was possible to get.
“Nice cock.” she smiled. “Come closer. Let me take a look.”
I moved closer to the bed, and she rolled over onto her side, reaching for my cock and taking it in both hands. “Mmmmm,” she purred, “I didn’t realize my boss had such a big cock.”
“And I didn’t realize my secretary was so horny.” I laughed.
“I’ve often wondered what it would be like to have sex with you.” she said.
“I must admit I’ve had that fantasy quite a few times.” I admitted.
“Really? I wouldn’t have guessed.”
“Haven’t you ever noticed me looking at your breasts?”
“Not really … you’re very sly, aren’t you?”
“Mmmm. Just keep wearing those button-through dresses, that’s all.”
She laughed and we kissed again, this time fondling each other’s bodies and then nibbling, kissing and sucking one another all over. Being careful not to place too much weight on her belly, I kissed her breasts, sucking hard on each distended nipple in turn. She groaned as I bit down, pulling the long, dark nipple into my mouth, feeling a small trickle of fluid drip into my mouth as I did so. I was kind of lying across her now and I felt her reach out between my legs, running her hand up and down my cock, then wrapping her fingers around it. I moved a little closer to allow her to get a tighter grip. At the same time I twisted myself so that I could lick her belly and all the way down to her navel.
Normally, I prefer shaven pussies, but I found myself enjoying the sensation of Lilian’s thick, dark hair against my face. She was fully aroused and her juices had already soaked her hair, filling the air with the heavy scent of her arousal. As I nuzzled her inner thighs, my fingers penetrated her moist bush to find her swollen labia, sticky with her juice. Gently parting them, I exposed the glistening wetness of her vagina. She moaned as I slowly ran my tongue from one end of her slit to the other, tasting the metallic saltiness of her on my tongue. We were both laying on our sides, her with one leg raised high and wrapped around my shoulder. I felt her press down on me as I thrust my tongue into her. At the same time, I felt her pull me towards her and take my cock into her warm, wet mouth, so that we were in a 69 position. She began giving me a very nice, wet, blow job. We went at each other for a while like this, my face buried in her cunt while she ran her lips up and down my shaft and caressed my balls. All of a sudden, she reached down and quickly slid a long finger into her pussy, wetting it with her juices. I thought she wanted me to finger fuck her, so I gently slid my own finger into her dripping hole, while continuing to suck on her engorged clitoris. In fact, the next thing I felt was her lubricated finger pressing on my asshole as she struggled to take more of my cock into her mouth. By now my finger was pressing on her g-spot and I felt her muscles tighten as she began to cum. At the same time, she was groaning, vibrating my cock to the point where I was sure I was going to cum.
“Hey, take it easy.” I protested, pulling away slightly, “You’re going to make me cum if you keep that up.”
She stopped sucking and began muttering something in Spanish while continuing to masturbate my cock. I returned to her pussy, nibbling her clit while massaging her g-spot. She came with a sudden guttural cry, never letting go of my cock. As I continued lapping at her pussy, my face was suddenly drenched in a new jet of fluid … she was actually squirting. I couldn’t hold on any longer and felt myself cum, spurting once, twice, and then again as she milked me dry. I felt her lips close on my cock and suck the last drops out of me. As our orgasms subsided, I turned to look at her. Thick globs of my sticky cum covered her face and streaked her thick black hair. She laughed and said, “It would make a great cum shot, wouldn’t it? I look like a real slut”
“Sorry.” I said, “I didn’t mean to cum so soon.”
“Don’t worry, I love it. You tasted great too.”
“So did you.” I laughed. “Man, you get seriously wet, don’t you.”
“I do when someone sucks me like that. You have a great tongue.”
She turned to me and we kissed again. I could taste my saltiness on her and no doubt she could taste her own juices on me as my face was drenched in them. As we kissed and caressed I felt my cock begin to stiffen again.
“So, are you ready to fuck now.” she whispered in my ear.
“Do you want me to fuck you?” I asked.
“Yes.” she gasped, harshly. “Fuck me. I want it.”
I turned her over into a kneeling position, ready to fuck her from behind, admiring the way her heavy breasts hung down beneath her.
“Look in the drawer” she murmured.
I leaned over and opened the drawer of the night table. Inside was a slender vibrator and a small bottle of lubricant.
“Do you see it?” she asked.
“I’ve got it.”
“Use that in my ass at the same time.” she whispered.
I laid the items on the bed and moved back behind her. Stroking the smooth taut olive skin of her thighs and ass, I spreading her ass cheeks wide open. Then I again licked her swollen pussy lips and then slowly slid my tongue up to her sweetly puckered asshole. Very gently, I began rimming her. She began to gasp, her anus involuntarily twitching as I gently swirled my tongue around the edge and then flicked at the taut little hole. She spread her legs a little wider and moved a hand back to her pussy, beginning to frig herself furiously, her juices now flowing freely. I continued to caress her asshole with my tongue as she experienced a mini-orgasm, then I judged it was time for the vibrator. Reaching over, I grabbed the lube and spread some on her ass, then teased her by working my finger into her. She groaned deeply. Grabbing the vibrator, I turned it on and slid it gently into her about half an inch at first and then gradually deeper as she loosened up. She began to buck her hips back and forth, still masturbating hard.
“Now fuck me. C’mon, fuck me with your cock.” she grunted.
I stood up, still holding the vibrator in place in her ass. “Do you need me to use a condom?” I asked.
“No. No condom. I want you to cum inside me.” she gasped. “Quickly. Fuck me.”
I slid the length of my rigid cock all the way into her. I guess every boss has fantasised about fucking his secretary. Here was I doing it for real. It was a beautiful sight. My hard cock thrusting slowly in and out of her, glistening with her juices, with a vibrator buzzing on her ass.
She began to moan more loudly as I increased the pace, burying my cock as far inside her as I could and probing deeper with the vibrator. Her moans turned into a high-pitched wail as I located her G-spot and she came.
“Harder.” she whimpered. “Fuck me harder.” Abandoning the vibrator, I grasped her hips and began to fuck her harder and harder. As she approached another climax, I felt myself begin to cum and with a final deep thrust, emptied my swollen balls into her. I held myself inside her for a satisfying moment, before slowly withdrawing and allowing her exhausted body to roll sideways onto the bed. A wad of thick white cum oozed out of her swollen pussy and slowly trickled down her inner thigh, glistening with her own copious juices. I watched in fascination as she collected it on her fingertip and slowly lifted it to her lips, her tongue savouring the salty flavour of our mingled juices.
“That was nice.” she murmured. “Let’s do it again in a little while.”
Suffice to say, we did. And again, and again. In fact, the rest of the weekend was spent mostly fucking… but that’s another story.
So, what do you think ?