Unexpected Nightcap

Author's note: A big thank you to Angel Love for volunteering to be my editor. She reviewed my work and in the process made it much better than it was originally. I believe that her insight and experience not only improved this piece, but will make the rest of my work even better. Thanks again.

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It had been a perfect day for a pool party. Things got underway early in the afternoon and there wasn't a cloud in the sky all day. It had been a hot sunny day and lots of drinking and eating took place during the afternoon and evening. The house was very quiet now. It was late; maybe a little after ten and the partiers had headed home. My wife Sonia had headed up to bed about an hour before announcing that she'd had way too much to drink and needed to lie down. I had just escorted the last guests to their car and returned to do a bit of last minute clean up. As I walked back in the house, I thought I'd get comfy, and changed into a pair of silky boxer shorts.

Having personally escorted most of the guests to their cars, I didn't think anyone was still in the house. Waylon and Willie were still playing when I walked into the bar in the lower level and to my surprise, Brandi one of our daughter's friends was sitting at the bar sipping a fresh drink. She's in her early 30s and I've had the hots for her ever since she blossomed into an adult. Brandi and I had been bantering back and forth all day teasing each other. It had started off as good natured kinda teasing, but as the day wore on the teasing definitely took on a sexual overtone.

Brandi is tall, about five ten with dark sexy features. She has shoulder length brunette hair, very small breasts and a pierced belly button which is usually on display. She still had on her tiny white bikini top but had changed into a short pleated skirt and three inch heels. She was sitting on a bar stool with her legs crossed and most of her thigh was exposed. I couldn't help but wonder if she had anything under the skirt. She definitely looked red hot.

As I walked across the room Brandi smiled and asked if she could fix me a nightcap. I smiled and replied, "Please do."

She slowly slid off the barstool showing lots more thigh as she did and moved gracefully behind the bar. She mixed Bacardi with diet and then headed back to the front of the bar and put the drink in front of me. As she did, she put her right arm around my shoulder and leaned around me with her left hand. She pressed her tits into my shoulder. Like I said, Brandi has smallish tits. The kind that always seem ready to pop out of whatever she's wearing, but they never do. It looked like she was continuing the teasing from earlier in the day.

I turned my head toward her to say thanks and without hesitating, she leaned in and gave me a little kiss on the lips and then stepped back. The kiss was more than just a peck but not long enough to become sensual. The smell of her perfume mixed with the muskiness of the day made my cock start to stir. As she climbed back on her stool, I could see that her nipples were now rock hard and straining against the thin fabric of her top.

As she settled in and crossed her legs she raised her glass to toast, "To a great party and having a great time." Our glasses clinked and we each took a sip. I wondered if there was a special meaning to the way Brandi said, "Having a great time."

I took another sip of my drink to stall a bit while I tried to assess the situation. Finally, I set my glass on the bar and turned a bit toward Brandi. I had decided to push this as far as I could, but I wanted to get there slowly. I told Brandi how hot she looked in what she had on and how great she looked today in the new bikini. As I continued to talk about how her outfits and complimented her great figure, I ran the fingers of my right hand up her left arm which was lying on the bar.

Brandi didn't flinch or try to move her arm. She blushed a bit and thanked me for the compliments. She slowly crossed her legs but I only got a glimpse up under her skirt. I continued to rub her arm as I told her how much I liked how hard her nipples were and how good her tits looked in the small white top. She just giggled nervously. I told her that lots of the guys and even a few girls had commented how hot she looked in the bikini. She took a sip and told me that she thought it was time for her to get a suit that showed off her body a bit.

I agreed with her adding, "I was really very happy that you felt comfortable enough to wear such a daring bikini to one of our parties. You know, when your suit is wet, it's pretty much see thru."

I think she was shocked a bit and she replied, "It is not Michael."

I had just enough to drink and smiled at her saying, "Hmmmm. Well, your areolas are about an inch and a half in diameter, and you only have a small tuft of hair above your otherwise shaved pussy. You know, the ladies I talked to really liked the way your pussy looked in your bikini."

I was having trouble reading the look on Brandi's face. I couldn't tell if she was angry by what I had just told her or whether she was proud. She was looking me straight in the eye and said, "Well, did you like what you saw?"

Now it was my turn in the hot seat. My cock was starting to stiffen as the conversation heated up. I didn't break eye contact with her and said, "I loved every minute of looking at your nearly nude body today. It almost fulfilled my fantasy about you."

Brandi smiled and thanked me again for the compliment and in her most coquettish voice said, "Tell me about your fantasy Michael."

My cock was now tenting my boxer shorts and Brandi could see the outline of my hardening shaft. I smiled back at Brandi and whispered, "It's for you to be completely naked and sucking my cock."

Without saying anything, Brandi put her drink down and slid off the stool. She reached behind her back and untied the strings holding her top up. When it was loose, the tiny white garment fell between us and landed on the floor. I could hear Brandi's breathing as she stood there topless in front of me. Her nipples began to grow even bigger. They were as least as big as my little finger and stood out at least three quarters of an inch. Against her smallish tits, her huge hard nipples looked incredibly hot and sexy.

Her eyes never left mine as she slipped a thumb inside each side of her skirt and pulled it down over her hips and let it fall to the floor. Underneath she was wearing a very tiny white sheer thong that did nothing to hide the patch of hair above her bare pussy lips. She grabbed each side of the thong and slid the tiny piece of gauze seductively over her hips and then it was gone too. She stepped out of her thong and then spread her feet slightly so I could get a good look at her bare pussy.

I adjusted my boxers so that my cock sprang through the opening. I looked at Brandi – she was just staring at my hardon. I said to her, "Now, suck my cock."

Brandi looked up at me coyly and asked, "Why should I do that Michael?"

I smiled back at her and responded, "Because you want to, but more importantly, I told you to."

She knelt in front of me and slowly lowered her head until I could feel her breath on my cock. Then she slid the head into her mouth and started to run her tongue all around it. After a moment, she slid my cock nearly out of her and tongued the tiny pee opening. Her mouth was hot and felt like velvet. I began to caress her face and head. She now was taking almost the whole length of my cock into her mouth and was playing with my balls through my boxers.

The feeling she was giving me was unbelievably good, but I wanted things to progress a little differently. I gently pulled Brandi up off her knees and pulled her to me. We were locked in a furious kiss and my tongue was busy where my cock had been just seconds ago. Brandi was breathing heavily and she was grinding her pussy into my knee. I captured each nipple between a finger and a thumb and rolled them back and forth. Brandi sucked in air and buried her face in my neck. I took her head in my hands and began covering her face with light feathery kisses. As I looked at Brandi's magnificent nipples I couldn't help thinking how erotic they'd look pierced.

I asked Brandi to turn around so I could see her cute little ass. She smiled coyly and when her ass was pointed at me she slowly spread her legs, bent a little at the waist and wiggled her sweet ass at me. She then moved backed in between my legs and started grinding her ass against my hard cock. After what amounted to a very hot table dance, Brandi turned around for another hot steamy kiss. While we were kissing, she played with my cock and I found her pussy. I played with her pussy lips, pulling them apart and tugging on them to see how big they might get. Once they had opened up, I found her clit and began to rub it softly in tiny circles.

Brandi's breathing started to get very heavy and she was bucking against my fingers as I played in her cunt. She was incredibly wet and it made playing with her clitty noisy. Brandi had stopped playing with my cock because she was now twitching and jerking under the pressure of my fingers on her clit. Suddenly her legs tightened and she buried her face against my neck. She stopped breathing for a second and then her first orgasm hit. She continued to ride my fingers and then she started shuddering again. She was into her second orgasm and I was going to take her to as many as she could stand. I stopped playing with her pussy for a minute so she could calm down a bit.

Brandi started to tongue kiss my ear so I decided it was time for another assault. As soon as I touched her clit again, she started twitching with yet another orgasm. I'd lost count as to how many times Brandi had orgasmed. Finally, she grabbed my hand and pulled it away from her pussy.

She gasped and all she said was, "Please, enough." I hugged her tightly and held her for a minute.

When her breathing had gotten back to normal I whispered in her ear, "It's time to fuck."

I turned her away from me and leaned her over the bar stool doggy style. I pushed my boxers over my hips and let them fall to the floor. The combination of her height and her heels, her pussy was just at the right level for my cock to slide right in. Her pussy was sopping wet and it only took one thrust to bury my meat all the way to my balls. She grunted as I filled her pussy. I started with slow strokes pulling my cock out to the head and then thrusting it back in slowly. I kept this pace up for a while and then Brandi began to push her hips back against me every time I thrust back into her. Brandi was furiously rubbing her pussy and I knew she was about to cum again. In seconds, Brandi was convulsing in the throws of another orgasm.

After a minute I slowly pulled my cock out of her drenched pussy. Brandi begged and whimpered for me to put it back in. Instead, I bent forward and stuck my tongue in her asshole. She jumped as if she'd been struck by lightning but I continued to rim her puckered opening as she continued fingering herself. When her rosebud was nice and wet, I stood up and placed the head of my cock against the tight anal muscle and slowly pushed forward. In three tries, my dick was all the way in. I knew that I was not going to last long in her tight backside so I picked up the pace and started to fuck her hard. She met my pace and her hips rocked against me on every stroke.

All of a sudden Brandi shuddered and froze for a moment as she started cumming yet again. I started thrusting faster as I could feel my orgasm approaching. Another couple of strokes and I shot my load into her tight velvety ass. I continued to fuck her and felt the silky smoothness as my cum filled her ass and lubricated my cock. We both were breathing hard, and sweating. I kept fucking her ass until my cock softened to the point I couldn't push it in anymore. I pulled my cock completely out of her ass. Brandi continued to lie across the stool while she recovered. In seconds my cum slowly oozed out and ran between her ass cheeks. I used my fingers to catch the gooey cum and rubbed it on her ass cheeks. I put two fingers against her opening and started to slowly finger her ass.

Brandi started moaning again and wiggling her hips at me. It was clear Brandi liked anal play. After fucking her ass with my fingers for awhile, I slowly, teasingly took my fingers from her backside. I lifted Brandi by her shoulders and pulled her tightly back against me. I reached around and played with her tits and pussy. Brandi pushed her ass into my dick.

She slowly turned around and said, "Michael, I haven't been fucked like that in a long time. That was wonderful. I'd forgotten how much I like having my ass fucked."

She kissed me hard with her tongue as she reached down to grab my cock. It was still wet from our combined juices. She slowly started jacking my cock up and down. My previously spent cock started to come to life again. As she did pumped my cock she said, "I want you to shoot your cum on me." I wasn't sure if I could cum again in such a short time but Brandi had my cock rock hard and I was ready to go. She played with my balls as she massaged my hardon. Between strokes, she would nibble my ears or slide her tongue in my mouth. I wanted nothing more to shot my load all over her. Her hands were working miracles and I could feel my orgasm approaching. A couple more pumps and I groaned to let her know I was about to shoot my load. She smiled at me and dropped to her knees just in time to catch the first glob on her tits. The next one hit her face and after that she held my cock against her tits until I was finished. Then she spread my cum all over her tits using my cock.

I looked down at her and said, "That was awesome."

She just smiled and said, "Thank you. You were awesome too. I'm all fucked out and I need to get to bed. May I spend the night Michael?"

I grabbed our clothes from the floor and led Brandi by the hand as we walked naked to the guest suites. On the way I told Brandi that I wanted her to join Sonia and me for coffee in the morning. Once in the suite, I tucked her in and told her I'd come wake her in the morning. As we kissed goodnight I noticed the dried cum all over her tits. Even a mess, Brandi looked incredibly sexy. I headed to my room to spend the rest of the night in bed with Sonia.

Well, that's the first time Brandi and I fucked, but it's not the end of the story. I'll chronicle those events in another chapter.