Its Only Fair 3

Holly and I decided to take a long weekend to an exclusive island resort in the Caribbean. The resort was very private and catered to clothed, nude and swinger clientele. The public areas of the complex were divided as such. With three separate pools, beaches and lounges guests could decide and feel comfortable with their surroundings.

On the flight over and once we arrived at the hotel, Holly insisted on having a wine and another and another. At 5' 6" and a size 1 a little alcohol goes a long way. I kept reminding her that she can't handle more than two drinks but to no avail. I virtually carried Holly into the elevator, down the hall and into our bed. Resisting the temptation of taking advantage of the situation I removed her street clothes, awkwardly pulled on an oversized t-shirt and tucked her into bed. I surrendered to the fact that this night would be uneventful and drifted off to sleep.

The next morning, I woke early as always and made some coffee, took a shower and decided to hit the gym. One look at my lover confirmed she would be sleeping a while longer. Now Holly is a sweet lady and very beautiful. Medium height, proportioned well, even after breast enhancement surgery, and blessed with a smile and a laugh that could melt the North Pole. Unless she has a hangover. All rules change. All bets are off. I learned to be patient while she grumbled and frowned her way through the dreaded morning after. This morning would be a perfect example of that behavior.

I placed a water with some aspirin next to a note on the nightstand and apparently made too much noise as Holly looked at me and growled "Go away!" I smiled and left our room as quickly as possible.

Even though most of the resort was divided by clothing or participation choices the gym was not. It was generally expected that you remain clothed, albeit minimal, while working out. No sex in the gym was allowed either. Fine with me, when I work out I need no distractions anyway. My workout clothes consisted of running shorts and running shoes. My plan was to hit the nude pool afterwards to finish my morning exercises. Hopefully by then the werewolf of room 302 will have returned to her human form. I started my chest routine and as I mentioned earlier I stay focused on my workout and don't like to chat or be bothered. Perhaps that's one reason at 45 years old I wore 33 inch pants, had almost abs and boasted larger than average arms and legs. I also kept my body shaved and maintained an all over tan. A nice, white smile and a touch of gray helped me to earn the occasional approving glance of a lady near me. With Holly often being the center of attention it didn't hurt her image to be next to a fairly handsome man.

After a few different exercises I noticed that a lady had entered the gym and was starting out on a treadmill and with headphones on took off a good pace. Since I like being left alone while working out I extend the same courtesy to anyone else in any gym. Add the fact that the in a swingers' community approaching the lady without acknowledging the gentleman is greatly frowned upon. After several different exercises for me and a couple miles for her she pulled a cell phone out of her gym bag and made a call. Since I couldn't help but overhear her conversation it was apparent her husband was being as ambitious as my girlfriend.

When she hung up she looked in my direction and said" Sorry, was I too loud on the phone?"

"Not at all!" was my reply. "I have a sleepy head in my room too." Hoping to generate a conversation. It turns out her husband didn't overindulge, he was a workaholic and hadn't taken a break in several months. We chatted and stretched for probably too long when her cell phone rang. My first thought was that my nice conversation with a good looking lady was now over. Luckily for me I was wrong.

As I left self-pity world and my attention returned to reality she said "Say hi to my husband Derek, he wants to talk with you." I must have displayed a surprised look to which she replied "It's Only Fair!" This phrase become popular when couples were stating limits and expectations. The general guideline was to acknowledge someone's partner before engaging in any activities. Derek was nice and put it simply that he was exhausted and that his wife was attracted to me and needed some attention. I promised him in return that I would respect any boundaries and would do my best to help her out. As Sherri put away her cell phone, she looked at me and asked "Aren't you going to call your lover, it's only fair?"

Gulp! Holly the Terrible. Holly the Walking Dead. Holly the Leave Me Alone Until Tomorrow or I'll Kill You. I walked over to the house phone and dialed the room number on speaker phone. After several rings she answered with an over dramatic "What!?!?" I recoiled and quietly told her about my new friend and that we may be spending some time together. We were both quickly informed that Sherri had permission to "fuck his brains out" as long as no one disturbed her again. Fair enough. I smiled sheepishly at Sherri and promised that my mate was actually a very nice person and I'm sure they could become great friends. Sherri smiled and took my hand in hers.

As Sherri led me past the clothed pool then the nude pool and opened the gate to the swinger pool I thought my smile would crack my ears. As an added bonus I took in Sherri's form on the walk. She was 5'3", thin, toned and tanned. Her efforts in the gym yielded great results. The gate closed behind us and she immediately removed her workout bra and spandex shorts. With a smile she went to the open shower and began washing herself. I stood mesmerized as she wet her hair and applied a body wash to her arms, chest and stomach. As she bent over to soap her lower half I received a nice smile that begged for me to join. I took the bottle of body wash from her hands and dropped to my knees in front of her. Starting at her feet I took my time and thoroughly washed up to both knees. I then turned her around and worked up the backs of her legs and onto a very nice, tight rear end. Making sure was clean and rinsed she turned around without any prodding from me. Now with Holly I learned to start out slowly and kiss and tease for a while. Sherri would have nothing to do with that. She grabbed the wash back into her hands, hastily placed one leg on my shoulder, washed and rinsed herself quite quickly. After dropping the bottle on the floor, she grabbed my hair and pulled me directly into her pussy.

When I started kissing and avoiding she firmly stated "Don't tease me. Go straight for my clit." It didn't take long before she pulled harder on my hair, pulled my face close and starting shaking. Her head tilted back and she let out a long, low moan. She stayed almost frozen for several seconds and slowly relaxed her grip on my hair and took her leg off my shoulder. The image of a small, tanned blonde climaxing in a flowing shower will stay in my brain forever. She looked down and smiling said "Derek's work has forced him to neglect my needs. It's been quite a while. Thanks."

Sherri helped me up from my knees and walked me over to an oversized pool chair with thick cushions. I laid on my back in the center when she kneeled between my legs and grabbed my raging hard on. She looked at me and smiled "It's only fair." What started out as teasing soon turned into a world class blowjob. Licking, sucking, ball fondling, she did it all. I rarely orgasm from oral sex but Sherri made it impossible not to. I soon warned her of her immediate future and she smiled and stuck with it. When the spasms started she continued like a real trooper. Soon I was begging for her to release me. The sensations were too much.

As I lay panting and recovering Sheri giggled and jumped into the pool. She shrieked as the cool water enveloped her hot, naked body. I rolled over on the cushioned bed and watched her swim around and splash. "Aren't you going to join me?" was all the tempting I needed. I dove in and actually enjoyed the change in temperature. We grabbed each other, laughed and flirted some more. The swim was relaxing and fun at the same time. When she swam to the bottom and came back up for air I took the opportunity to wrap my arms around her and give her my best passionate kiss. She responded. We swam together to the closest ladder and walked back to the pool lounge. We laid side by side and explored each other's bodies. Her nipples and breasts were amazing to touch and suck and she obviously enjoyed the attention. As I rolled her onto her back and took my spot between her legs she paused and asked if I had a condom. Dam house rules. If one partner requests a condom the other must oblige them. Apparently my disappointment showed as Sherri smiled and stated again "It's only fair." Remind me to punch the guy that came up with that saying, was my thought.

Even with the condom on she felt amazing. I took my time pushing slowly, enjoying the feelings and making sure she was feeling it also. This time I was in control and I wanted to make it last. The bad news is when I wear a condom it takes a long time for me to cum. The good news is when I wear a condom it takes a long time for me to cum. I'm not sure how much time had elapsed since we left the gym but I didn't care. Just as we both starting sweating, grunting and really getting into the unbelievable feelings Sherri whispered "We have company." I paused what I was doing and looked towards the gate. There stood a younger couple, both attractive but both covered in loose fitting sweat outfits. The young man was about 6'2", dark hair and handsome. The young lady was short, thin and wore a baseball cap so it was hard to see what her face looked like.

I looked at Sherri and continued my slow, controlled thrusting. The fact that we had an audience only spurred us on. I kept the pace slow, almost too slow for Sherri but her body was responding just fine. As I shifted positions from laying to resting on my knees and elbows to allow for some faster action, it happened.

"Excuse me!" "You're standing in front of the gate!" "Do you own the whole place!"

Hey everybody it's Holly, back from the dead and charming as ever. Now, even hungover Holly was a sight. She had obviously showered and put on her favorite bright yellow thong. The top covered enough of her boobs to be legal and the bottom had plenty of material in front and not very much in back. The sharp yellow material contrasted with black clasps at the sides of the thong bottom and the front of the top. She had ordered an entirely too expensive bottle of water and topped it off with wayfarer sunglasses and a white ball cap. Still, absolutely stunning. Holly practically pushed the young couple out of her way and pranced over to the large lounger next to Sherri and I. With a look of pure annoyance, she glared at Sherri and reminded us "I told you to fuck his brains out. What are you waiting for?"

Now Holly and I have both enjoyed watching each other engage in sex on several occasions but not when she's in her mood. The fear that I may shoot too early definitely just left. I looked at Sherri and started moving slowly again. She closed her eyes and focused on the task at hand. After a couple of minutes, we started enjoying the outdoor fuck we were having. Once again we reached the point of grunting, shifting and twitching. The kisses became more passionate and the movements a little more irregular.

Then I heard "Excuse me, Missy? You, young lady. Are you just going to stare or can I put your friend to good use?" The young forgotten couple looked at each other and then back at Holly. "Yes, you two. There's no one else here is there?" "Oh my God! Boy, come here and take off your clothes!" The two checked with each other, then with me. I smiled and nodded yes. The young man walked the twenty feet like he was going to the principal's office. Standing in front of Holly with his right side to Sherri and I he awaited further instructions. Holly looked into his eyes and began to fondle her nipples under her bathing suit top. After a minute of this she snaked a hand under her thong bottom and started teasing herself. Her bathing suit was unlined so any trace of moisture caused it to cling to her body.

One of Holly's favorite positions was to lay her legs flat and prop her upper body up on her elbows. She has said this position allows her to watch the action and positions any dick that's inside of her to hit the spot that gives her a great orgasm. She rose to her elbows, laid her legs flat and scooted towards the end of the lounger closer to the young man. She looked up at his tall body and barked "Take off your clothes and put on a condom!" The boy pulled his sweat shirt up over his head and both Sherri and Holly gasped simultaneously. This kid was built like an Abercrombie model! Holly took her left foot and ran it over his picture perfect abs and chest. When she stopped he leaned forward and lowered the pants of his outfit. If the ladies were impressed with his top half they were amazed at his bottom half. Well defined legs, tight ass and a larger than average cock. He was already half erect having watched Holly's little show. Holly then looked at him and asked about his condom. Uh oh, the principal is going to be upset! He, they, apparently didn't have any protection with them. Now Sherri and I had laid and watched without much movement. It seems we both liked to watch as much as being watched. If anything I could feel her throbbing around my latex encased cock.

Holly looked at the apologetic young man and shook her head in almost disgust. She unsnapped the side clasps to her thong and let the front piece sag loosely at the same time she took her foot and began teasing the young man's dick. It didn't take long until he was fully erect and breathing heavily. "Listen to me carefully. You can put the head of your dick up against my favorite bikini but don't move. You can't push or I'll make you stop. I'm going to get my morning orgasm since my boyfriend is fucking someone else. Do you understand what I've told you? Just the head, don't push and don't ruin my new suit." He moved a little closer and I noticed a slightly perturbed look on his face. Holly was playing with fire and her last set of instructions just fueled that fire a little more.

Since the oversized loungers set up high it wasn't difficult for her young stud to slightly lower his body and place the head of his above average dick at her protected entrance. She looked at him sternly and while propped on her elbows began rubbing her clit. Sherri started wiggling beneath me and reminded me that I had work to do. I started slowly and moved side to side instead of thrusting. This suited Sherri just fine. After a few minutes Holly let her lean backward and closed her eyes. A true tale sign she was working towards a climax.

Sherri stopped squirming and pulled my ear close to her mouth and whispered "Look at his ass!" Beg your pardon? "He's wiggling his ass and it looks like he's in a little deeper!" She was right, this young guy had taken the slow approach and it was working. It wasn't just the head but about one inch out of eight that was helping to tease my girlfriend into an orgasm. Suddenly Holly looked at her young sex toy and frowned. He backed up and with a scowl she perched herself back up on her elbows and started again.

What happened next was completely unexpected. The forgotten young lady who was with the young man had removed her sweats and walked toward Holly and her boy toy. Wow! A top heavy gymnast is my best description. Light, flexible and bouncy was how she walked over to their lounger. Holly had just started wiggling on his dick and threw her head back again. This was the young lady's perfect opportunity. She crawled legs first behind Holly and then placed her legs on top of Holly's arms and under her body. This meant Holly could not move her arms out or down and was essentially in a full nelson trapping her upper body in a raised position. Holly looked around and quickly realized she couldn't move. Her arms trapped by the girl and her legs now held down by the boy. The girl wasted no time in bending over with a gymnast's flexibility and planting a long sensuous kiss right on Holly's mouth. At the same time, she snaked her right hand into Holly's bottom and her left under the left side of Holly's top. My girlfriend had a large cock pressing dangerously against her pussy, a small hand lightly tickling her clit, two fingers teasing across her left nipple and a tongue swirling with hers.

Holly's body immediately responded by wiggling and grinding. Her head now lay in the young lady's lap and she could not escape the lingering sensual kiss. The younger girl stopped the kiss and looked at her boyfriend. He backed up just enough for the girl to grab Holly's thong and quickly pull it off her shaved wet pussy. He eased forward until he once again had about an inch inside Holly's now unprotected swollen lips. He looked at me awaiting permission and I quickly nodded. The girl started fingering Holly's clit again with light and slow touches. She took her left hand from Holly's extended nipple, grabbed her hair forcing Holly to look into her eyes.

With a near evil grin "You insulted us, teased my boyfriend and now he's going to fuck you and cum inside you. It's only fair." Holly didn't get a chance to respond as the girl resumed her kiss, her nipple teasing and her clit teasing. The boy also held Holly's legs down and proceeding to inch more and more of his cock into her. Sherri and I could see Holly's body relax into the girl's lap. She was on her way to an intense orgasm whether she wanted to or not. The young lady released her kiss and gave her beau the go ahead to move faster.

The boy increased his pace slightly and eventually had all of his width buried inside Holly. The girl adjusted her legs to not hug Holly's arms so tightly and this allowed her to bend over further and trap Holly's right nipple with her lips. Her left nipple was soon being teased and pinched by the girls left hand. The boy resumed the task of tickling Holly's clit. Apparently this young man knew his way around a woman's body and rubbed indirectly and lightly. With all of this simultaneous stimulation Holly never stood a chance. Her face was partially covered by the girl's left boob as she was turned towards Sherri and I. Her eyes were closed and her mouth open. I could see her hands grasping at nothing in particular. Then with a combination giggle grunt her body went rigid. A silent scream, curled toes and vibrating body clearly showed she had been tag teamed into orgasm. She kept this position for nearly a minute and then slowly slumped down with her head in the girl's lap. The girl sat up releasing both nipples and signaled the young man to stop rubbing Holly's clit. He obliged but then put Holly's legs straight up in the air. He looked at his girlfriend and then at me. This time the look was not seeking permission but telling us both he was claiming his prize.

The minute he began a stronger rhythm, Sherri stated trembling and talking to no one in particular. The combination of watching three beautiful bodies fuck in front of us and my persistent side to side motion put her over the edge. I looked down in amazement as the pleasure took over her body. As soon as Sherri began calming down everyone could hear the groans of the young stud. He was leaning forward slightly, sweat glistening off his enviable body and staring down at Holly. His girlfriend barely held Holly in her place but she wasn't going anywhere. After another minute it started to happen. His strokes became more erratic and face became flushed. In an instant his ass muscles clenched and his head threw back. Holly reacted as if an electric shock went through her body. I knew right then that someone else had cum inside my partner for the first time. His tremors continued for quite a while and soon after evidence of his cum leaked around his dick and down Holly's ass.