Families Vacation

In the August before my sophomore year of college, my family and I went on vacation with the Williams' (Mr. and Mrs. Williams, Cory, Lauren and Carly) and the Romas (Mr. and Mrs. Roma, Tommy and Vicki) to Miami. We stayed in one of those timeshare communities. It was four stories of condos around the exterior with a pool in the enclosed interior. It was all within about 100 yards of the beach.

On Wednesday all the guys were going to play golf, but I had other plans. The night before, during a private moment after dinner, I pulled Mrs. Williams aside, "Ellen, I want you to meet me in my room tomorrow at 11am for some fun while everyone else is out."

"No Rick, we can't. I was going to spend the day at the beach with your mom and Mrs. Roma."

"Did you forget already? It was just a month ago that you promised I could ask for anything and you couldn't say no."

"I didn't forget," she said with teeth clenched, "I just don't think we should be messing around on this vacation with all the families around. As soon as we get back home, then we can do whatever you want."

"Sorry, I'm calling it in now," I said with a smirk.

"Fine, 11am, I'll be there," she said reluctantly.

It was just about 11am. My mom had left for the beach around 9:30am and knowing her she'll be there til the sun goes down. My brother went with all the rest of the guys to play golf around 10:30am. I pretended to be sick to get out of it. Around 11:15 I went out my door and leaned over the railing by our fourth floor condo to see if she was coming from her apartment on the second floor near the opposite end of the building. I went back inside, but when she hadn't shown up by 11:30, I made my way to the elevator in the middle of the building. As I rode the elevator down, I saw Lauren and Vicki by the pool. I got off and made my way over to them. They were both reading magazines. Lauren was wearing a red and white striped bikini top and black shorts. She was tan with long black hair. Vicki had on a green bikini top and khaki shorts. She had a darker tan than Lauren and long brown hair with curls.

"Hey girls, do you know if our moms went to the beach already?"

"My mom went to meet your mom on the beach about 10 min ago," Vicki said putting down the magazine she was reading.

As Lauren put down her magazine, Carly showed up and claimed the empty lounge chair next to Lauren. It was hard to believe she was only 18, a year younger than the other two. She looked like she was at least 22. "Mom says she has a headache and is going to lay down for a while."

"Well I guess that answers that. I'll just wait for my mom to get back, to ask her then," I said. "You girls have fun today." I left them and went back to the elevator. I rode it back to the fourth floor, but instead of going right towards my condo, I made a left and made my way to stairs on the opposite end. I made my way to the second floor and hung the right towards the Williams' condo.

As I got to the door, I looked back towards the pool and saw the three girls talking and laughing. I knocked on the door and after a minute the door opened.

"No, you shouldn't be here," Ellen said as she tried to close the door in my face.

"No, we should be back in my place right now," I said as I forced my way into the condo." She was wearing an oversized pink tank top and black shorts over what looked like a light blue bathing suit. I closed the door behind me and followed her down the hall as she walked away. "Did you forget?"

"No, does it look like I forgot?" she asked as we walked into the main bedroom. Laid out on the bed was a sheer black teddy, garters and thigh high stockings. I felt my cock swell in my shorts as I pictured her in them. "I couldn't go through with it. Not here."

"Well then you shouldn't make promises. I'm going to fuck you right here and now, " I said as I took off my shirt and loosened my shorts. They fell to the floor and my hardened cock sprang forward.

"I said not here," she insisted putting her hands on my chest and pushing me away. I wasn't about to give up. I pulled the tank top over her head and even though she resisted and tried to stop me, I unbuttoned her shorts and let them fall to the ground. She stood there in her strapless, one-piece light blue bathing suit. Her nipples were hardened and poking through the nylon material. I leaned in and kissed her on the mouth. I pulled her closer and her arms weakened against my chest. I grabbed the top of her suit and yanked it down. We continued to kiss intensely as I fondled her right breast and she stroked my rock hard shaft.

I laid her onto the bed and told her to close her eyes. She complied and I kissed down her neck and along her collarbone. I then took each of her hands and kissed them before using each of the thigh high stockings to tie her hands to the headboard. She opened her eyes and looked from hand to hand and then stared at me in shock as I stood at the foot of the bed.

"I'm going to enjoy this," I told her with a smirk. I spread her legs and kissed her inner thighs. I felt a shiver run through her and she arched her back. I worked my way to her moistening neatly trimmed mound. I ran my fingers around the outside before licking her pretty pink pussy lips. I bent her legs and pushed her waist up slightly. I then began to lick her asshole and played with her clit between my thumb and forefinger. She moaned with pleasure and squeezed her legs around my head.

"Yes, mmm, you're tongue feels so good."

"OH THAT'S THE SPOT," she yelled as I began to finger her now soaking we pussy. I shifted my tongue to her clit and sucked on it.

"I'M GOING TO CUMMMMM!"

"YESSSSSSSS," she exclaimed as her back arched before collapsing back to the bed.

I moved up the bed next to her and kissed her softly on the lips. I then positioned myself on top of her and slowly slid my throbbing cock into her moist crevice. She let out a long gasp of pleasure as each inch entered her. I began to quicken my pace. Her arms strained in their restraints as her legs wrapped around my waist.

"You feel so good inside of me," she said with teeth clenched.

I squeezed her left breast and flicked the nipple with my tongue as I continued to fuck her with a steady motion. I then felt her back arch again as her legs spread and her toes curled.

"OH YESSSSSSSS!" she yelled after biting on her lower lip.

As her body went limp again, I pulled out and moved up the bed. I knelt by her face. "Taste your self on my cock," I told her as I slid my cock between her lips. She sucked my cock and ran her tongue around the shaft and it wasn't long before I was ready to cum myself. I pulled out of her mouth and stroked my cock, preparing to shoot my load onto her face.

"NO! Not on my face," she pleaded.

"Put it back in my mouth"

"NO! STOP! DON'T!" she begged loudly.

"NOOOOO!!" she yelled.

"STOP! Leave Her ALONE!" said a voice as footsteps ran down the hallway.

We both turned our eyes to the door. At the same time, I shot my load across Ellen's face. I looked back down at her and she looked back toward me. "I told you not to cum on my face," she said disappointed.

A gasp came from the doorway, and we both looked back in that direction. The previously clutched umbrella fell to the ground with a crash and there stood Mrs. Roma with her jaw practically on the floor.

Apparently I had forgotten to lock the front door of the condo behind me. Mrs. Roma had come to check on Mrs. Williams to see how she was feeling.

Mrs. Roma finally composed herself and began to walk away.

"Sandy wait, we should talk about this," Ellen called after her.

She came back looking toward the floor with her eyes shielded, "Ellen, I thought you were in trouble. I never would've thought you were tied naked to the bed with Rick, our sons' friend, ejaculating on your face."

"Sandy, you don't understand . . ."

"Oh I understand; this is obviously the 'great sex' you've been having. I thought it was with your husband, not another guy, let alone our sons' friend."

I began to untie Ellen's arms as she struggled to sit up, "Adam is always at the hospital and has barely touched me. You remember how we sit and talk about how handsome and sexy some of these young guys are? Just the other day we were having drinks and you mentioned how you wished you could be "fucked silly" by a young stud. Have you seen Rick? I think he qualifies."

I felt aglow with pride upon hearing this, while getting dressed.

"Oh I think I've seen enough of Rick. I can't get the image out of my head and I don't think I want to hear any more about it!" she exclaimed as she stormed off.

"I need to go after her, but first I need to clean myself off and get dressed. I can't believe you came on my face."

As Ellen went into the bathroom, I went out the door after Mrs. Roma. I got to the elevator just in time to see it close with her in it. I tried pushing the button again, but it did not open. The other elevator arrived and the girls got off.

"What are you doing here?" Lauren asked.

"Just had to drop something off for your mom, you girls take it easy."

"Bye, Rick," Lauren called after me.

I skipped the elevator, as someone else had gotten on the elevator and was going down. I ran for the stairs and sprinted up them two at a time until I reached the fourth floor. I saw Mrs. Roma nearing her condo, which was across from mine. I looked back towards the Williams condo and the girls were gone. They had probably gone inside. I reached Mrs. Roma just as she was opening the door.

"Rick, go away. I just need to be alone right now."

"I know you're kind of in shock right now, Mrs. Roma, but don't be mad at Ellen. You just need to talk this out," I suggested, following her into the condo. This time I locked the door behind me, so no one could over hear our conversation.

"I don't know what I'm feeling right now. I just witnessed my best friend getting a facial from YOU! That isn't something you can easily process. I can't get the image out of my head," she stated as she took out a small glass and poured a little vodka into it. She quickly drank it down and poured another, which she also promptly drank. I put my hand over the glass before she could pour a third. She just stared at me.

"I don't think you should pour any more. Besides she said you were talking about how you wished you could do something similar just the other day. Everyone deserves to be happy, and this made Ellen very happy," I told her.

"The funny thing," she said as she pulled the glass away and poured another, "The young stud we were talking about was you." She then smiled and gulped down the vodka. She walked down the hall, "She just decided to make it happen. I thought it was a silly fantasy. I think you should leave now," she told me as she entered one of the bedrooms.

I was frozen with shock. It was quite a risk for Ellen to be talking about me like that. What if Mrs. Roma noticed something between us? Well I guess that's out in the open now. Before I could leave, I had to make sure Mrs. Roma was going to keep what she saw to herself. I entered the room and she was leaning on the vanity and staring into the mirror.

She saw me in the reflection and turned around. Her expression was one of sadness mixed with anger. She leaned against the vanity and flipped the hair out of her face. "I said, I think you should leave now," she stated more firmly.

I just stood there a step inside the room. While she looked beautiful, with the sun shining through the blinds making her hair and body glow. Her shoulder length hair even more golden brown, her tanned body illuminated, and she was wearing a one-piece red bathing suit with a sheer untied kaftan over it. For the first time in my life I was ready to go against my natural instincts. I felt my cock swelling in my shorts, but my moral compass was telling me to leave. I turned to leave, when she asked me to wait. I stepped toward her and she stood up straight. I noticed her squeezing the sash of the kaftan in her right hand.

"Why did you have sex with Ellen?"

I wasn't sure how to answer it, especially since it had been going on for a while now.

"You do realize that she's married, don't you?" she asked before I could answer the first question. "She's the mother of your friend, she has a family," she declared as she stepped even closer to me. "What makes this OK?" she yelled at me and pushed me back. I almost fell onto the bed but caught myself. She was about 5'10", and as close as she was she barely had to look up at me. Her eyes welled up and she clenched her fists.

"Doesn't Ellen deserve to be happy? She's a beautiful woman who isn't getting the satisfaction she deserves. So I helped her out with that."

"So if I think I deserve more, would you tie me up and cum on my face?"

"No, I wouldn't"

A look of surprise appeared on her face. "You don't think I'm as deserving as Ellen? I think your cock disagrees," she said and then promptly pulled my shorts down, revealing my fully erect member.

I gave her my own look of surprise. "I didn't say I didn't find you sexy. It's obvious I do. What I meant was you deserve something else." I took her hand in mine pulled her closer. I then leaned in and kissed her softly on the lips. As our lips parted, her eyes remained closed and she seemed to be floating on just the tips of her toes. I slid the kaftan off her shoulders and her eyes opened just in time to see it glide to the floor.

"Wow," she said softly as she looked into my eyes. Her hand was still holding mine. I brushed the hair out of eyes with my other hand before leaning in and kissing her again on the lips. This time with a little more pressure and our mouths opened ever so slightly and our tongues touched. After our lips parted this time, I leaned in and kissed her neck. She purred with delight and I worked my way along her left shoulder sliding off the strap of her bathing suit at the same time. I proceeded to do the same on her right side. I looked her in the eyes and she gave me a slight nod as she gently bit her lower lip. I began to kiss along her collarbone before slowly peeling down her bathing suit and revealing her seemingly perfect tanned 38D breasts. I continued to peel down her suit until it fell to the floor. Her pubic area was completely smooth and the only area of her body apparently untouched by the sun. We kissed again and she took my shirt off over my head and began to kiss my chest.

Together we pulled down the comforter and got into the bed. We kissed passionately and then she nibbled on my ear lobes. I slid down and proceeded to fondle and lick her breasts, circling her nipples several times before finally sucking and nibbling on them. I traced the curves of her body with my right hand before sliding it between her legs. Her body shivered as I inserted first one, then two fingers into her soaking wet crevice. We kissed again as I continued to rub the inside of her pussy with my two fingers and her clit with my thumb. Her hand had found my throbbing member and she began to stoke it and fondle my balls. We continued at this pace for a few more minutes until she looked into my eyes and declared she was ready.

She pushed me onto my back, got onto her knees and positioned herself over my cock. "Oh my God, that feels so good," she said through clenched teeth as she slid down onto my cock. Her pace was quick at first as she rode me hard. I massaged her breasts and pinched her nipples, as she bounced up and down.

"You are so hot. Your pussy feels so good around my dick."

Our hips began to move in sync, my upward thrusts with her downward motion

"YES! YES," she moaned.

"I'm gonna cum," I told her through heavy breath.

"I'm almost there," she said as she arched her back and leaned back on her hands. Her breasts bouncing as I held her hips.

I blew my load inside of her, but continued to move with her while I was still hard.

"Oh GOD! YESSSS! OHHHHHHHH!" she yelled before collapsing on top of me. "That was amazing," she panted.

We just lay there for what seemed like forever as we tried to catch our breaths. She rolled off me and laid on her back. I turned my head and stared as her breasts rose and fell. Once we had begun to breathe normally again, we both turned towards each other on our sides. I ran my hand through her hair and she kissed me softly on my lips.

"That's what you deserve," I told her with a smile.

She laughed and smiled back and me. "I don't think I've felt like that in years. That was just . . . wow."

"I think so too."

"But we can never do it again. It has to have been a one-time thing. As much as I would love to do that all the time, it wouldn't be right. Don't worry no one will ever hear about this or you and Ellen."

As much as I wanted to protest, I understood. I got dressed again and she put on a purple robe. She walked me to the door and kissed me softly one last time on the lips before opening the door. She poked her head outside, "The coast is clear."

"Bye, Mrs. Roma. You're an amazing and beautiful woman. Let me know if you ever need anything."

She smiled at me and I held her hand until the last possible second as I walked out the door and around toward my condo. I looked back at her door and smiled before going inside.

*****

As always the names and some of the facts were changed to protect the identities of the characters.