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."
