Me & Shari Pt. 03 - Sink or Swim

It was pool party day. I checked out my tan in the mirror before dressing, I have not been this dark since I was a kid and spent every waking moment outside playing, only difference, I was all over tan thanks to several lovely days on Shari's secluded patio. First suit was a jock strap style, open in the back and had a hole in the front that my cock and balls came through, the elastic around the opening was just tight enough to act like a cock ring and push everything out front. Next was a speedo style that was just big enough to cover what I wore under it. The front pouch cupped and supported me, making sure I was on display. Lastly was a pair of surf shorts just to be decent for the drive over. I threw on a T-shirt and sandals to complete my look. Not too bad for an old man, I told myself.

Normally I would be excited for another fun filled night of sex, sex, and more sex, but I had not been in a relationship like the one I was in with Shari for one of these before. I kept telling myself that we had met and a party just like this only a month before, but I was not sure how I was going to react watching her with others, or how she would react while watching me. I looked at myself in the mirror again and told myself that everything was going to be fine.

I grabbed my food for the party from the fridge and headed for the car. Backing out of the drive I noticed how early I was, but I really could not wait to see Shari. She had refused to let me see what she was going to wear but teased me repeatedly that I was going to love it, so I would not tell her what I was going to wear either.

I drove slower than usual to eat up part of the hour I was ahead of schedule, but it was still a short drive to Shari's house. Arriving 40 minutes early was not too bad I told myself. I rang her doorbell and let myself in, a habit we had started with each other a couple of weeks in to seeing each other. Shari shouted from her bedroom that she would be right out and to make myself comfortable. I got a glass of water and sat at the kitchen table admiring the view out the back of the house nervously waiting for her beauty to overpower it.

She emerged from her room dressed in a flowing sundress that was all orange, red, yellow, and pink that made her tan, several shades darker than mine, absolutely glow. The sleeveless dress was low cut to show nice cleavage and only buttoned to midthigh, showing off her gorgeous, tanned legs. I whistled at the sight of her, and she gave me a spin so the dress would fan out.

She gave me my first deep enthusiastic, kiss of the night and sat beside me. I figured you would be early and try to catch a peek, so I was ready for you, she teased. I confided in her that I was apprehensive about tonight. I felt that we had grown close over the last month and had seen each other exclusively. I told her that, even though we met at a swinger's party and that I was comfortable with that lifestyle, I had never been to one with someone I cared about deeply and cared about me as well. She thought a moment and asked I wanted to only do things together for this first time. My turn to think, I told her no but let's start out together and things would work out as the night progressed.

She stood and gave me a quick kiss. I tried to grab her and pull her onto my lap be she resisted. She promised me that the first and last one that was going to be fucking her tonight was me, but I had to wait to see the goods when everyone else did. I gave her a playful slap on the butt and was told not to start something I did not have time to finish. I looked at her questioningly and said, Oh! We have not traveled down that road yet, have we? She said that, considering how we met, she thought maybe it should wait. Good point was all I could answer. She did then come around the back of the chair and put her arms around me. We're Good, she said, reaching down between my legs, grabbing my package. I turned and kissed her cheek and said, we most certainly are.

Jim and Jan's house was just outside of town, The house sat on top of a knoll with a long lane winding its way up the hillside, there was a large circle drive in front that allowed for plenty of parking. A marked path led around the side of the house to the back of the house where the walkout basement emptied out to a huge pool and patio area. A sunken hot tub that could hold ten people butted up to the side of the pool so you could easily slip from one to the other. The rest of the back yard, well there was not any, the pool and patio filled all the level space and the rest dropped off steeply down the hillside. Complete privacy as far as you could see.

Jan greeted us as we came onto the patio. I introduced her to Shari, and she was sorry that they had to miss the last party, she had heard it was a good one. I told her that I had sure benefitted from it. We were running early and only a couple people had arrived so far. Shari offered to help finish getting things ready with Jan and left me with a quick kiss. I joined Jim at the grill to offer the required assistance to the master griller. He said he only needed a fresh beer and some details from last month. I got the beer and told him briefly about my last month with Shari. He told me that he was happy for me and could not wait to meet her.

Right on cue, Shari came out with some plates for the table, and I beckoned her over. She slid right in under my arm, and I introduced her to Jim. She greeted him with a kiss and told him how much she loved the house and grounds. He thanked her and, looking her up and down, said, if you like it now, just wait until it full of frolicking naked nymphs and horny men. She teased back and said that she hoped it happened soon because she had too many cloths on for as warm as it was. I laughed because I knew that her swimsuit was all she had on under her light summer dress and I could not wait to see it, too bad protocol was to wait until after we ate.

More people started arriving and Shari excused herself to go help Jan with the food they brought. I had to think that she was fitting right in, she greeted those that she knew from last time and introduced herself to those she did not and told them that she was here with me. These pool parties always seemed to have a big draw with the group, like it was the mandatory party to be at.              Jim loved it because he got to show off his place and his grilling skills and have some type of sex with everyone in the group. Jim had the grill handled and I had already taken a couple of platters full of food the roasters to stay warm. I joined Shari who had relinquished her food gathering duties to visit and acquaint herself with the group, pretty sure that Jan had told her to go mingle and be with me.

Kurt and his wife, Becky arrived late, claiming that they had babysitter problems, their daughter called wanting them to watch the kids last minute, they had to decline, did not go over big with her. Shari greeted them like long lost friends giving them big, long hugs and kisses that they also shared with me. Last to arrive was Gloria, flaunting all she had with an entrance that surprisingly did not include a trumpet fanfare. She was dressed as a mermaid, and I have no idea how she walked up the pathway in her getup. Only Gloria would come to a pool party orgy dressed as a mermaid. Come to find out, that outfit was going to stay on all night. It had Velcro openings everywhere she needed them, and I do not think I saw her once having sex anywhere but the pool.

Jim rang the dinner bell and told us to eat and drink so we could all get to the merry lovemaking. We all obeyed and lined up to enjoy the feast, eating leisurely and beginning to start the flirtatious conversations. I watched Shari interacting with the others in the group. I was amazed at how easily she fit in, flirting with the women as much as the men and even promising Gloria and Suzi, the other trans woman in the group, that they were both going to get a turn with the two of us before the night was over. I found Chuck, the inventive member of the group, and thanked him for the gear he donated the night of my party and told him that I wish he could have been there to see it work. He told me that he had heard it was a success and assured me that it would be used again soon.

The afternoon sun was just starting its decent into evening when food clean up started. The food that needed to stay cold was removed to the house and all the rest was left out and covered to be grazed on throughout the evening. I checked the pool temperature, and it was perfect, as usual for Jim. Street clothing was being shed for the swimwear or less underneath as the pool started filling with bodies. Someone had helped Gloria to the steps and once she sat and got wet, her mermaid flippers pretty much disappeared showing her in all her glory.

Shari finally stopped helping Jan being hostess and asked me if I was ready to see her new suit. I pressed my hardening cock into her tummy with a hug and told her that I had been ready for weeks. She undid the few buttons holding her dress in place and let it fall.

I joined a few others nearby with wolf whistles. Her suit, what there was of it, was the perfect shade of orange to make her tan look deeper than it already was. Two small triangles of cloth cupped her breasts but allowed her perk hard nipples poke out. Narrow strips of material crisscrossed her body down to an equally small triangle of cloth covering but not hiding her perfect cock and balls, more strips of cloth emerged from between her legs in back, framing her bouncy, tanned ass. Wow, that is the perfect suit was all I could say. Let's see what you countered with she said, pulling my shorts down. The speedo I wore barely contained my bulging cock being thrust forward by the jock I wore under it. The white material also enhanced the tan I was sporting as well. Let's get wet she said.

We fell into the pool together with a big splash and emerged into a water fight, making sure that everyone too close was involved rather they wanted to be or not. I patiently waited until she turned away from me enough that she didn't notice how close I was and wrapped her in my arms. We wrestled around in the water until I had her facing me. I slid one arm around her neck, locking her face to mine and used my free hand to push the little triangle of swimsuit off her breast. She stopped struggling and settled in for some fierce necking. Her hand slid inside my trunks and pushed them down, letting my dick free.

She stroked me to firmness and wrenching free from my embrace, took a deep breath and disappeared under the water. Her mouth enveloped my cock, sucking it hard and fast. It felt like a long time before she came up for air but barely gasped when she did. I do not know how you even practice to do that, but I decided that it would be fun, so I did the same thing. A deep breathe to fill my lungs and under the water I went. I pulled the bottom of her suit to the side and found her cock. I covered it with my mouth and started working it with my tongue. I felt it growing in my mouth until it was nice and firm. My lungs gave out and I had to surface.

That was fun I told her once I caught my breath. We held each other for a few minutes, enjoying being close. She whispered in my ear that we had a few friends that wanted to join in. I told her that I guess I was ready to share and with a kiss, turned to embrace whoever was closest. Jan was right beside me anxiously waiting and Jim was beside Shari, also waiting his turn. Jan is a tall, thin, athletically build blond who played Division 1 basketball and could have turned pro but decided on kids and marriage instead. She was a trainer/assistant coach for the university now and could probably still out play most of the girls she coached. Jan told me that she had missed my oral skills and her pussy was aching for it.

We moved to the side of the pool, and I helped her up to sit on the side. I told her that I would never refuse a beautiful woman such a request. I lifted her shapely legs up on my shoulders and started kissing my way up to their delicious center. Licking the water from her legs, I teased at her meaty vulva lightly with my tongue. The folds of her mound opened wider with each pass of my mouth. Only when she had been properly teased and readied did I lower my aim and pressed my tongue against her asshole and start the slow trip up between her legs.

When my mouth finally parted her thick full pussy lips and my tongue dove into her, opening her meaty love channel, did her magnificent clit pop out of its hiding place and beg to be sucked. I ignored it for the moment, feasting on the copious juices flowing from her. My hand found her small A cup tits and I rolled her hard firm nipples between my finger and thumb. Holding herself up with one arm, she grabbed my head with the other and pressed my hard into her crotch.

Her quick little squeals let me know that she was coming, that and the fact that she was bouncing up and down against my face. I stopped everything I was doing and let her ride it out. I heard her finally take a big breath, and then I started back at her in earnest. Her cum covered my face. I pulled back enough to fill her sopping pussy with three fingers, her ass with my pinky, and took her clit into my waiting mouth. I had enjoyed doing this to her many times and had always loved the results. Jan had a big sensitive clit. Almost three inches when she got good aroused. I held it in my mouth and flicked my tongue over it while working my fingers in to her holes. When she started to climax a second time, I pulled my little finger from her ass and slid my hand easily into her pussy.

I pressed my hand against her clit from the inside and used my mouth to suck hard on the outside. She locked her legs around my head, holding me firmly in place while she rode out a massive orgasm. Her squirting juices ran down my arm into the pool and covered my face and chest. I eased my hand from her and gently held her shrinking clit in my mouth until she was able to recover enough to release me from her leg lock. Once free, she pulled me up and gave me a kiss and thanked me for getting her warmed up and going. She stood, a little wobbly and went off in search of her next victim.

I looked over at Shari and Jim who had finished their activities. They were shaking their heads at Jan and laughing. I moved closer and asked if they thought I did it right? Jim told me that Jan had told her that I ate pussy better than any guy or girl that she had ever been with, and it was always the best way for her to ready for a night full of fucking. Shari pointed to our friends, Gloria and Suzi and told me that speaking of a night full of fucking, they were waiting for what was promised. Shari gave Jim a quick kiss and led me away to my fate.

Jim, by the way, was also very athletically built. A Lacrosse player in college and a computer geek, he went on to build a very successful software company. Rather than retire when he was bought out, he worked out a deal that let him keep working for the company for a percentage of the sales of what they bought from him and any future products he designed on a graduating scale. The more things he brought to market, the more he made from them, and he only worked when he wanted to. He also was one of the better endowed guys in the group, second only to Chuck who sported a thick twelve incher and lasted like a porn star.

Shari led me to a huge lounger where the gurls were waiting. We were joined by Billie, Chuck's petit wife. She was all of four foot six inches and weighed a hundred pounds soaking wet, and yes, I have seen her take Chuck's monster cock all the way in all three holes. She was a little spitfire and her eyes always seemed to sparkle with mischief. Suzi, I knew but she had only started coming to the parties recently and I do not think we had ever hooked up. They laid me down on the longer with two of them on each side. Shari took my speedo off but left the jockstrap around my cock and balls. She stood and released the one clasp that held her swimsuit and as it fell off, she was still wearing a body strap that framed her breasts and came down to wrap around her cock and balls also. Everyone else was naked and ready for fun.

Suzi and Billie started kissing and fondling each other. Gloria and Shari both went down on my cock that had not had near enough attention yet this evening. They took turns filling their mouths with it. Suzi and Billie broke apart and joined in. Suzi straddled my head letting me feast on her well stretched cunt while she sucked Suzi's dick. Suzi was well endowed as well, at least seven thick inches, Billie had no trouble deep throating her and when I looked up to watch, I could see if bulging in her throat as Suzi fed it in. The warm mouths on my cock deserted it. My ass was raised up and a cushion was pushed under it. Lube was generously applied, and Gloria's cock entered me. Shari stood over me and fed her cock to her.

Billie lifted off my head then arranged herself over my cock and plunged herself onto it while eating at Shari's ass. Suzi lowered her glistening cock to my waiting mouth. The five of us fucked this way for several minutes, each of us urgently wanting to climax. I came first, filling Billie's pussy, she came when I did and shoved her tongue into Shari's ass as she did, Shari let the tongue ramming into her ass force her release and she emptied her load into Gloria's waiting mouth, Gloria rammed her cock into my clenching ass and filled it with her hot cum, I sucked hard and fast on Suzi's cock and she filled my mouth with cum that I greedily drank down.

While we crashed into a tangled, sweaty heap, breathing hard and still moaning with pleasure. Becky brought over some beers and canned drinks for us and told us that it was quite a show and she wanted in on the next one. We slowly untangled and sat up to recover. There was still a lot of action going on as well as some that, like us, were recharging. I noticed Jan on another longer like ours. Chuck was under her, and she was riding his huge cock with abandon while Jim did his best to keep up from behind. I could from the angle that they were both filling her pussy and you could hear her squishy cunt devouring them both. Kurt stood over them and she was devouring his cock into her hungry throat. We all watched amazed at the amount of cock she was filled with and when she could, begged for more.

Billie jumped up and told us that if she needed more then someone should give it to her. She walked around to one of the side cabinets, reached in and pulled out a dildo shaped like a horse cock and a bottle of lube. She climbed on the lounger behind her, squirted a big glob of lube on Jan's empty asshole, smeared some on the dildo and pressed it slowly into Jan's hungry ass. Jan's cry of I need more changed to yes, yes, yes. Billie picked up the rhythm to match the two cocks trusting in and out of her pussy, gradually feeding more of the eighteen-inch dildo into her ass. When it was all inside of her except for what Billie needed to hold, Billie leaned over and started talking into Jan's ear.

Jan stopped screaming and with a gush of cum and squirt and everything else in her body, climaxed violently. Her entire body throbbed with her orgasm and all three cocks that filled her holes jettisoned there loads into her at the same time. They all collapsed into a heap like we had just a few minutes ago except for Jan who went from cock to cock lapping up the last drops of cum while the huge dildo was still sticking out of her ass.

I whispered to Shari to remind me never to say I needed more around Billie. We all erupted in laughter. Billie reached out to Jan and started cooing and touching to get her calmed down. The guys moved out of the way so Billie could caress and talk to her. We could hear Billie telling Jan that it needed to come out, but Jan just kept saying no, leave it. It seemed like she was in a climax coma. Shari surprised me by hopping up and padding over to help Billie talk Jan down. Gloria noticed me watching that cute ass wiggle across the patio and punched my arm. That ass is yours for as long as you will have it, you know. I gave her a hug and told her that I sure hope so. Gloria started stroking my cock and it responded accordingly. I noticed that others had started the same type of activities. I reveled in Gloria's attention and reached for her cock as well. I watched Billie and Shari comfort and talk softly with Jan.