Fortunate Man
Introduction:
A new family moves in next door. They encounter financial problems and I jump in to help them out – for a price.
I am one fortunate man. I am a sinner that the good Lord has given a great blessing to. This is a true story that happened a few years ago. The names and events are not changed as I really don’t give a crap.
I am an older gentleman who has been overly successful in my business adventures. I have a been able to stash a small fortune while living a very comfortable lifestyle, residing in an upscale neighborhood in New York. Remaining single with no children has enabled me the flexibility to travel for my work and devote the time to make my mark. Along with that, I have been blessed in having my manly needs attended to. There have been a few ladies along the way that have fulfilled some pretty wild desires. I must say, being well off finacially is something that works in my favor. Women always love a man that can provide.
But of all the women in the world, none compare to Jocelyn. She is truly the most erotic, sensuous and wonderful person that has ever been. It all started several years ago……
I was close to my neighbors, the May’s. A nice family and we had a lot of good times together; helping each other out and holiday dinners together. Sadly, they had to move for their jobs. We had a good farewell weekend and their house went empty.
A couple months later, a new family moved in just as the Summer started. A young couple, Mike and Jocelyn, with their 10 year old daughter Emma. Right from the start they seemed like such a nice family. But one thing was obvious, they did not seem to have the means to afford this neighborhood. He drove a beater of a car and they did not have enough furnature for the house. They brought a home in a neighborhood they wanted, not what they could afford.
They soon made a replacement in my life that the May’s left. As we got to know each other through the summer, we got into a kind of routine together. I had them over for dinner at least once a week. I had time and they were busy with work and young Emma. Mike had a job as an accountant and Jocelyn worked at the grocery store that gave her the flexibility to care for Emma after school. When the holidays came through, they had me over for Thanksgiving dinner with her parents there. I was over for Christmas morning watching Emma unwrap her Santa treats. His parents were there for a pretty nice New Years Eve gathering with some others in the neighborhood.
On her days off and when Emma was at school, Jocelyn would hang out at my house. My work did not require me to be in an office every morning. My schedule was dictated by the work. Some weeks it was 18 hour days. Other weeks just a couple hours with phone calls and emails. When Jocelyn was over during the day, we would chat about all kinds of things. Soon we got to know a lot of intiment things about each other. I must say, I did rub a few out thinking what I could do with her. As Spring was approaching, she started opening up some more. Her and Mike were having some real difficult financial issues. They knew it would be hard when they moved in, but a few unexpected expenses in home ownership seemed to pile up. I did my best to assure her things would work out.
As I got close to Jocelyn, I also got close to Mike. I treated him to a weekend away in Vermont at Stowe for a late season ski. We had a great time on the slopes. In the evening we sat around the lodge and got toasted. He too opened up to me about their financial issues. He loved his family and so much wanted to provide them a good lifestyle. He pushed things to the limit but just could not get there.
In my personal life, I was becoming frustrated. I was “in between” lovers. I had no steady companionship. The best I had was a few high end ladies that charged for the night. Good for an outlet, but always left a void.
I remember the weekend it really started. March 15th. The weekend before St Patty’s day; which should be national holiday. We had a cookout and a few beers at my place. A nice spring day. I was cooking some ribs on the grill talking to Mike while Emma and Jocelyn played in the yard. Mike mentioned that he was at a loss and could not make the mortgage payments. They already stopped paying some of the utility bills. I was thinking how in the hell can things go that far south in less than a year. Not much planning on their part moving to this place.
This became a turning point in my life – much to the better.
Later in the evening we were back at their place. Emma was asleep and we were in the living room yapping and having a few more beers. Soon enough, they both shared their financial concerns. They were not sure how much longer they would be living there. They said how lucky I was to be able to afford such a life without any worry. I reminded them I had no family. They were the lucky ones.
I had everything but companionship. I told Mike how lucky he was to have a sexy wife. She blushed a little. When we were alone i have told her she is sexy and erotic. This was a first to mention it in front of Her husband. Jocelyn was a tall slender woman. She had small breasts but they just screamed sexy. Then I broke the ice. I said to Mike, if I could have just a moment of what he has, I would gladly pay to keep them where they are. Jocelyn perked up and asked what that meant. I said if I could have one day a week with her, I would give whatever it takes to keep them as my neighbors and friends.
Mike looked at Jocelyn as she asked what would that entail. I said if I could have her compainionship for just 24 hours each week, I would pay their mortgage and all the utility bills. They both knew me enough to know I could afford it and that I would follow through. They both started asking questions. What exactly would happen in the 24 hours? I said I would want Jocelyn to be my compainion from noon on Saturday to noon on Sunday each week. What happens would be between to two of us. We would be a couple for that time. Then at noon on Sunday she goes back to Mike until the next week. No secrets from Mike. He would be entitled to know everything that happened if he asked. As long as I felt fulfilled in the compainship park, I would pay the aformentioned bills.
They looked at each other with an inquisitive gaize. Each seemed to be asking the other for approval. I took the last swallow of my beer. I asked them to think it over and talk to me tomorrow. With that, I got up and left them alone.
The next day, Mike came over. We talked about what was said the night before. He seemed agreeable. He said Jocelyn felt the same way. They had spent the rest of the night talking about it after I left. They very much wanted to stay in the neighborhood and they both like being next door to me. I spelled out some rules. I learned long ago in my business dealings that laying out the conditions for both parties at the start is a solid path to success. I said I need companionship and someone to hold. That if Jocelyn could belong to me once a week as close as she belongs to Mike, the deal was good. The condition was that she likes it. I am not one who forces something on a woman. If she did not want my companionship or did not enjoy being with me, I would not want it. She truly had to want this. And so must he. If he felt uncomfortable or was uneasy about it then we would not proceed.
A couple of days later, Mike and Jocelyn came over to my place. They said they both were wanting this. I said that emotional events like this can take unexpected turns. As things progress we need to be open and honest. But also remember this is a business transaction and we must keep focused on what benefits each of us need and what it is we must do to earn them. It was Thursday. We would start on Saturday.
I poured a fine brandy for Jocelyn while Mike and I had a single malt scotch, Oban. We toasted for the future.
On Saturday morning I went over to their house around 9 am. I sat with Mike and reviewed their overdue bills. Damn. He was right. He stopped paying all of the utilities months ago. I wrote checks for the electric, water, trash and fuel oil. I paid the cable and upgraded them to the top package. I paid the mortgage 10 days early. I made a spreadsheet for myself to note when each was due next. I asked Mike to put them in my door drop when he gets the invoices. I asked that he change the billing address to me. I just took his mortgage coupon book.
While we wrapped this up, Jocelyn was talking to Emma. She told her daughter that mommy was going to be spending some special time with Joe on the weekends. She explained how I was a good friend looking out for them and she in turn would be looking out for me. She gave Emma and big hug and kiss goodbye. She got her overnight bag and kissed Mike as we walked out the door. It was 1230.
Back at my place. It did seem a little strange and new. Countless times we sat in my kitchen and talked alone. This afternoon was different. Jocelyn put her bag down and gave me the biggest hug. She said she could never thank me enough for what I was doing to take care of her family. I stood there and held her for a long while. It was so nice to be holding her. Feeling her embrace and smelling her hair.
Soon enough, I took her up to my room. My bedroom was rather large. You had to pass through a sitting room before entering the master bedroom. We set her stuff up and she unpacked her toiletries in the master bath.
Back downstairs I made her a light lunch as we nervously chatted. There was a feeling of unease as both of us wondered what the next 22 hours would hold. But as always, I had a plan to work from; ready to adapt if the situation changes. Always have a end game, develop the plan, be flexable with the plan. After lunch we curled up on the couch and watched a movie. A great way to spend a rainy afternoon. It was nice just to be holding her. After the movie and a Family Guy episode, we got ready for dinner. I took her to a very nice restaurant on the water, Harvest on Hudson. The rain cleared and after dinner, we sat outside and had a few cocktails. What a beautiful woman. All dressed up, smiling with the moonlight in her hair. After a long evening out, we went back to the house.
I was exhausted and she looked pretty tired herself. We went up to my bedroom. I held her and gave her a kiss goodnight. Our lips touched. Our mouths opened our tongues touched. Wow. What a feeling. I broke it off and said goodnight. We have a long road ahead together. No need to rush anything tonight. I went into the sitting room and closed the doors to the bedroom.
We slept late and around 8am I was up making breakfast. Jocelyn came down in her nighti looking all cute and bed heady. Her nipples were sexy, poking through under the light material. I gave her a kiss on the cheek and poured the coffee. Over bacon and eggs we shared more stories of our lives. Through last nights dinner conversation and this morning we learned more of each other than since she moved in. After breakfast she took a shower as I cleaned up. She watched the news while I took a shower. When I went into the master bath, I saw the she left her panties on the bathroom vanity. Right there for me. I smelled her fresh scent. Mildly moist in just the right spot. They were hot. I rubbed one out as I sniffed them. I blew my load right on top of her wet patch.
After my shower, it was almost noon. I came downstairs and gave her a hug. I said I put the rest of her things in her bag. She smiled, thanked me and we kissed. It was so nice holding her. She asked me to lick her lips. Then she got her bag and left. I looked out the window and she looked back at me. As Jocelyn got to her door, Mike and Emma greeted her. She hugged Emma. Then she gave Mike a passionate wet kiss. Devious lady. I could work with this.
The next Saturday at noon, Jocelyn came over. She set out her stuff in the bedroom and came back down. I asked her how Mike felt about this. She said he was unusually turned on. She got home last weekend and unpacked and Mike asked her if we ‘did it”. She said no but it was a fantastic weekend. She told him we kissed. And about leaving her panties for me. While unpacking she noticed the cum on her panties. She said she got all giddy about that. She was rubbing the wetness when Mike noticed. She handed him the cum soaked undies. She said he put them to his nose and smiled. He started rubbing himself. Then he wrapped the panties around his cock. Spanking the monkey a few times, he blew a load on top of mine. All I could say was,”Nice”.
She got up and gave me another passionate kiss. Then she looked in my eyes and asked if we would be making love this weekend. I told her, “Soon, but not this weekend”. (Plan: Wait until she asks – and politely turn her down twice. The end game works when they are begging and you have the upper hand).
But I did have a very special weekend planned. She is such a lovely woman, she deserves to have some nice things. This afternoon we would be going shopping. We went to the Woodbury Commons Outlets. I took her to the stores she likes. Jocelyn picked out several casual outfits with matching shoes. She got a couple evening dresses. Shoes to match each outfit. She picked out some very nice earnings and necklaces. We made several trips back to the car.
The last stop was Victoria Secrets. I said this is a purchase for me. She had fun picking out different items and I was showing some things to her. My heart and my imagination were running as she held up different outfits. Finally we filled a few bags and headed to the car.
On the way home we stopped at Doubledays for dinner. The talk started with her saying how happy her and Mike have been over the past week. No more financial issues. It was tearing them apart for months and now it seemed like it was over. Even Emma noticed a glowing change in the atmosphere. Jocelyn wanted to pay me back in any way she can. I told her that the companionship was worth ever penny. Her and Mike saved me as much or more than I saved them. (Plan: Be overly generous in the beginning. Tell them they are being even more generous).
When we got back to the house, it took a few minutes to unload the car. She brought the loot up to my bedroom. She said she wanted to try everything on again and give me a fashion show. I could do nothing but agree. I told her I would retrive one of my finer bottles of wine, two glasses and will be waiting in the sitting room.
I was back in my sitting room, resting in my leather recliner when she came out. She first came out in one of the evening dresses with the earrings, neckless and handbag. Damn. She looked like a hot lady ready for a night on the town. She came over to me and we toasted the wine. After showing me a few poses, Jocelyn went back in the bedroom to change. She kept coming out showing off all her new clothes. After the last L.L.Bean outfit, she said there was one last set to show. I refilled our glasses and said bring it on.
She started with the least revealing nightgown. Then she came out in just a matching pantie and bra. Good lord almighty! What a well crafted body. My heart still pounds when I think of this first time I saw Jocelyn’s body. She is truly one beautiful and erotic woman. To this day I don’t know why I did not get up and bang her right there. She turned get back to me and bent over. Oh fuck me. What an ass. She stood straight up and went back to change. After a few sets, she said time for the last one.
The last set was a pair of crotchless panties and a bra that had holes for the nipples. Sweet baby Jesus. Oh sweet baby Jesus and that is Holy. My first view of her well trimmed bush and those sweet nipples. All the money I shelled out over the past couple weeks was worth every penny of what I was looking at now. She did her few poses and turned around. Again she bent over. I had the best view of her lady bits and an almost clear view of her rosebud; well framed by the panties. I almost blew a load right then. Seriously. I was so turned on by the build up that I almost came.
Jocelyn turned around and walked over to me. I stood up, not hiding my boner. We hugged and she pressed her body against me. We kissed. I was in heaven. She whispered in my ear that she wants me to take her. I pulled back an looked into her eyes. I told her I wanted to, but tonight was not the night. We got some things to make herself feel good and special today. We will have time later. Jocelyn said she would be right back and disappeared into the bedroom. She came back out with the panties she was wearing all day. She said to have fun with them. We kissed again and said goodnight.
I put the panties on the table and went to sleep. I wanted to wait until the morning so I could give her a fresh treat for to go home with.
The next morning I got up early and ran an hour on my treadmill. A day always goes better when you wake up to a good workout. I put on the coffee and went in to wake up Jocelyn. Her sleepiness was just so sensuous as she rolled over in bed to smiled at me. I kissed her on the forehead and said coffee is ready and soon the french toast She slept in the nude. As she got up I turned to walk out the door. As much as I wanted to soak up a good view of her nude body, I had to be the one in control. I had to let her know I will look at her when I want to.
She came down in one of her new nightgowns. Perky nips and sweet hips. We had a nice breakfast. After we were done, she was doing the dishes. I brought up the fact that she now had a lot of her clothes upstairs still in bags. I said I would clear one side of my walk-in closet for her things. I would go out later this afternoon to buy a dresser for her. I told her the clothes she got were for my pleasure. I wanted to see her well dressed. They would stay here.
After taking a shower, she had fun unpacking her things into the closet. I emptied some of my older stuff into bags for goodwill and consolidated what was left. It is strange and almost a waste to donate $1000 suits to goodwill, but an expensive suit that does not fit just right is worse than a good fitting cheap one. Jocelyn moved in and switched her stuff around several times, trying to find out what worked best.
I disappeared into the bathroom for my shower. Before I got in, I took the panties she gave me last night and added a special Joe present. After my shower, I got dressed for the day.
It was almost noon. Jocelyn got her bags packed. I let her know I added the panties to her bag. She gave my another passionate kiss and let me for her husband and daughter.
That afternoon I went over to the gun club to bust a few caps. It was a nice early summer day.
Chapter 2: A Special Weekend
That Tuesday evening I invited Mike and Jocelyn over for dinner. Emma, of course,was in tow. I was ready for the next big step.
After dinner, Emma went in the den to watch some cartoons on Netflix. I sat down with Mike and Jocelyn to discuss our next time together. I came right out and stated the next time I will to be making love to Jocelyn. Her face flushed when I said that. Mike seemed to have his ears perk up a little. But, I added, I am a very practical man. All of us would get a full battery of testing done. STD’s can be a very serious issue. I wanted to have unbriddled passionate times with Jocelyn. Looking at her into eyes, I said we would be exchanging lots of body fluids.
We would get tested the following evening. I had the talk about what to expect – and that is what we should do if one of them comes back positive for something. We had to all agree that there would be no questions or judgements. If a positive comes back we simply get treated and move on. If it is something that is not treatable, we need to have a discussion of what to do from there. Also, I had my nuts cut a few years ago. I would add another test for them that validates I’m still sterile.
Then, we had to owe it to each that we would remain to each other. If any of them stray, they could come to me in confidence. We agreed before that there would be no secrets, but there are times that some confidentiality is in order. They both agreed. I let them know that I had to travel to Dallas for business and would be gone over the weekend. This gives us some time to get all the results back before the next time. Since I would not be able to have Jocelyn for the weekend, I wanted the two of them to go have dinner on me at the Harvest on Hudson. Get a babysitter for Emma and spend some time together.
The next evening, all of us went to get the blood work drawn. A professional staff at this place. The three of us getting blood taken while Emma was running around. No strange looks from the ladies there. Pros.
I made arraignments with the restaurant to take care of them and headed off to Dallas. If I could – more like when – I pulled this project together, I would come out with enough to cover the cost of this endeavor and then some. As the plane took off I ordered a stiff drink and settled in for a good flight.
I returned the following week. All the tests came back negative. Now I was getting a little flushed. This coming weekend I would be enjoying the body of a very beautiful woman.
Saturday at noon my doorbell rang. I let Jocelyn in and we had a long kiss. We held each other tight. We were both ready for this.
We had a few snacks and chilled for an hour or two. Then she went into the master bedroom to get ready. She took a long bath and enjoyed the soak. Once done, she took her time getting dolled up. Stockings, a nice evening dress, earings, hair done.
When she came down to the living room If was in awe. A limo pick us up to go to an early dinner. I wanted us to be able to enjoy the wine.
All through dinner, I was just wanting to rip her clothes off. We had a wonderful meal and a couple bottles of wine. Most of it was a blur. Bad business form to get too excited for something. But this something was just too much.
Limo ride back was nice as I held her in my arms. No fondling yet.
We got back early in the evening. As I closed the door behind us, we were ready to take each other. I gave her a kiss and our hands went all over our bodies. I pulled away and took her by the hand walking upstairs to my bedroom. We stood by the bed and started kissing again. My hands slipped down to her buns and I started massaging them through her dress. I pulled up on the back of her dress and was now rubbing her buns over her panties. She had her hands on my sides and slide them over to the front and over my bulge. I pulled her panties down and she stepped out of them. My hands were all over her soft ass cheeks.
Jocelyn was rubbing my cock through my pants and dropped to her knees. She undid my belt, unbuttoned my pants and unzipped. She pulled my underwear down and my cock fell out in front of her. She grabbed it and moved it around on her face.
I’m evil. I stopped her and asked to to be still. I got my phone out and dialed Mike’s number. I handed the phone to Jocelyn, I told her to tell Mike she loved him and that we were now home from a lovely dinner. On her own, she added that we were just starting the best part of the weekend. As she said this, I rubbed my cock down the bridge of her nose.
After she hung up, she undid my shoes and took my pants off. I damn near ripped my buttons out getting my shirt off. She was still in her dress and on her knees in front of my nakedness. She took my cock and put it against her lips. I slid my hands on either side of her neck and under her ears. I grabbed her head as she took in my cock. What a most exquisite sight. Looking down at her beautiful face as my cock slid in. Those cheeks moved in as she gave a good suck. Jocelyn’s tongue rolled around the head as she sucked some more. In a slow rhythmic motion, I started moving my hips and pulling her head back and forth as I gently pushed my cock in and out of her face. Oh how lovely the feeling of the way she worked her magic.
Jesus must love me.
Time was lost on me. After a while of doing this, I stood her up. We took her dress and bra off. We embraced our naked bodies and kissed. I pulled us over to the bed and sat on the edge of the bed with her standing in front of me. Jocelyn got back down on her knees to start sucking my cock. She expertly rolled her tongue down my shaft and under my balls. She licked and sucked on the little boys. She flickered her tongue all the way down almost to the backside. She came back up and swallowed my cock. I was leaning up watching then fell back to close my eyes and just enjoyed life. What an awesome feeling. A great blowjob is proof enough that God loves us. She said don’t hold back. After an eternity, I got to the edge. I stopped her for a second and got all the way on the bed. She came up with me and I played with her titties. Then she got back to work. I felt it coming up. I moaned and instinctively held her head. She had me half way in when I spurted. She moved her hand along the lower shaft as she sucked in my cum. She moved her tongue fast along the underside of the gland as she sucked for all she was worth and swallowed it all. Fucking A.
She held my cock as she pulled it out of her mouth. Jocelyn looked up and smiled. She milked the snake and a droplet came up. She rolled the tip of her tongue across my cockhead and took in the drop. I could hardly breath. The rush was unbelievable.
Jocelyn moved up and we hugged. We kissed. (guys- women appreciate a real man that will kiss her after taking a mouthload of you cum; it’s a way of saying tank you). She snuggled in and was rubbing her wet pussy on my left thigh. I had caught my breath by now. I pulled her to sit on the edge of the bed as I knelt on the floor before her. Her sweetness was right in front of me. Her milky smooth legs were opened up and I was looking right at that glisteing pussy. I started rubbing her thighs and quickly worked up. I started rubbing and exploring her cunt. Rubbing her labia and mons. Expolring and enjoying the beauty of her. She was getting wetter with each rub.
Then I cupped my hands under her buns and my thumbs were on either side of her lady lips. I spread her lips open. I moved in and licked the insides of her freshly exposed labia.
Fucking A.
I have been down on a lot of women in my days. More than I can remember. But I know this – none have ever tasted so nice as Jocelyn. Maybe it was reality or maybe like a placebo, I wanted so bad for it to be true that it was.
Some beautiful women I have eaten were pretty rough down there. Sometimes the Lord does not bless them. You take them out or a nice date. Maybe get to know them for a few dates. You get a little chemistry going between each other. You get all worked up. Alone in your sanctuary and get down to business. You work your kisses down to her sweetness and BAM. It aint so sweet. Not so with Jocelyn.
Jocelyn was well blessed by a tasty pussy.
I licked her labia then up around her clit hood. Down again on the outside of labia. Back to pulling them apart again and licking the inside. She grabbed my shoulders and let out a nice moan. It is good to be appreciated. I moved to lick her clit this time. Gently. Gliding my tongue around the hood and over the clit. I worked back own to her opening. I rolled my tongue in and out like a little piston. With a free hand I rubbed her clit. Her juices flowed down my chin. It was wonderful.
I grabbed her ass cheeks and pulled her in as I felt her ready to orgasm. She pulled my head into her as she started panting and let out a load moan.
She relaxed as I gave her post orgasm kisses around her pussy. Both of us were feeling alright. We moved up to lay on the bed next to each other. We snuggled and kissed. By now I was rock hard again. Some precum, or maybe some leftover from earlier, wiped along the outside of her thigh was we embraced.
Now I was ready to take her. I rolled on top of her and my cockhead naturaly came to rest at the entrance to her pussy. I gave her a big kiss. She reached down and guided my cock into her pussy. I worked it in and out slowly at first to make sure we had well lubricated parts. She was soaking wet; making this real easy. I picked up a rhythm and started moving faster. She bucked her hips up against me in perfect harmony. My halls were slapping against her making that familiar noise. I already blew a load , so I was set to last awhile.
I pounded alway. I arched my back and bent down so I could suck on those boobies. It slowed the pace down but neither of us complained. The feeling was intense. She began to climax as I picked up the pace again. She screamed for me to keep it up as she crossed the edge. She wrapped her arms around my back and pulled me in as she howled. Holy crap did she yell. An unbridled howl. As her orgasm subsided, I slowed the pace and gently moved in and out. Then came to a halt.
I rolled her onto her belly and pulled her hips up as I kneeled behind her. I spread her ass cheeks and looked down at her ass and pussy. I easily slid my cock in her cunt and started pounding away. I pushed and pulled on her hips as I watched my cock moving in and out. I watched how her cunt lips molded perfectly to my cock. Her juices flowed. I then pressed my chest to her back, reached under and started pulling on her nipples. Twisting and pulling ( but not too hard). She was banging her hips back and forth against my cock. I slid my right hand down and rubbed her clit. Alternately sliding two of my fingers along her cunt lips feeling my cock and balls slapping in and out.
I let go of her pussy and grabbed her hair with my right hand while still rolling the nipple with my left. I had a good hold on her hair and pushed her face down on the bed. She let out a loud moan and was yelling for me to keep fucking her. Good Lord I hope she is not this loud when she has a kid in the house. She was letting loose.
With the encouragement, I leaned back and pulled her head up. I had a good knot of her hair and pulled it tightly back. I was fucking going at it as I slapped her ass with the other hand. A cute little bun giggle was returned. What a good bitch. She screamed again as she seemed lost in another orgasm. Her face flushed as she gasped. I pounded away for a bit and slowed up. I pulled out and we caught our breath.
I went over to the night stand and poured a scotch. I took a sip and smiled at Jocelyn. What a beautiful lady. What a hard on I still had.
I laid on my back and pulled Jocelyn to take top. She pushed my head back and smiled at me. She moved her head down and took my cock in her mouth. My cock and balls were all wet from her cunt juice. She sucked on that cock and took in all she could. She licked the head clean and started licking my ball sack.
She then climbed on top and easliy slid her cunt down on my cock. She rocked a little then leaned forward to kiss me. Our lips and tounges exchanged a pluthera of body fluids. After the kiss, she leaned back and started riding for all she was worth. She worked those hips like nobodys business. Our bodies glisened in the heat. Life is awesome.
I felt my balls coming up and I was getting ready to explode. I pushed my hips up to meet hers. I grabbed her hips and pulled her down hard, let her ride up and pulled her down again. She knew it was coming and kept at it. Then I blew. What a feeling of release and my sperm squirted into that pussy. The wave of euphoria.
Jocelyn fell down on top of me and we just hugged again for awhile. What a feeling of accomplishment and companionship. A nice set of boobies pressed against my chest.
She rolled off of me and I moved over over to sit on the edge of the bed. I took a sip of scotch and she found the blow towel. We got up and held hands walking down to the kitchen. I needed a glass of cold grapefruit juice. She got an ice water and we stood there naked and not saying much. Not much needed to be said.
We went back up to the bedroom. I got towels out for us and we took a nice long hot shower together. The boner was long gone as we washed and explored our bodies. Getting familiar with each other. It was nice. We dried each other off and went back to the bed. We curled up together in our nakedness and I was out cold in a minute.
We slept late. She got up before me and went into the bathroom to pee and brush her teeth. She came back to bed and started gently fondling my balls. I started to get chubby. She felt the reaction and just moved her head down to take it. She gave the best morning after blowjob ever. It was just about the most relaxing and enjoyable cocksucks I have had. I held her head as I blew a small load. The good girl swallowed nicely.
We got up, took another quick shower, dressed and went to Dobbs Diner for Sunday breakfast. We sat there talking about everything and nothing over a good cup of coffee and eggs benedict. The sun came in the window and lite up her profile just right. I was one forunate man.
We went back to the house and it was almost noon. She got her things ready and headed for the door. We embraced and kissed. Jocelyn got down on her knees and unzipped my pants. She took out my cock and rubbed it all over her face. She then tucked it back in and zipped me up. She opened the door and headed over to her house and back to her family. As she stepped out, her door opened and Mike and Emma waved. They were standing there waiting as she walked over. Then I saw she had the blow towel in her left hand. She got to the door and gave Mike the towel as she picked up Emma. Emma gave her a big kiss on the cheek. She leaned over and gave Mike a kiss. Devient lady.
Chapter 3: A Routine (with a few kinks)
We developed almost a routine. Jocelyn came over every Saturday right at noon. Emma and Mike stood at their door to kiss her goodbye and wave.
Jocelyn and I really got to know each other as the summer came up. Our weekends consisted of watching movies on the couch, going to dinner and sometimes a trip to a broadway show. I learned more about her than I think Mike knew.
But a business deal this was. I paid some bills and got something back.
As the inevidable happened, shark week came upon her one weekend. I said she needed to do something to make up for it. And God bless her, for she came through. I asked for a really nice backrub and blowjob. She had me take a nice long hot shower while she got things ready. I came out of the shower into the master bedroom. She had candles lit and some soft music playing. She had me lay face down on the bed. She started to rub my sholders and neck. She took her time and worked my back and arms. She knew how to relax her man.
She rubbed my buns and worked my upper thighs. Now I was getting a little hard under there and had to adjust myself a few times. She continued down my legs and gave a kick ass foot massage. Then…..she worked her way back up to my buns. She massaged them and slowly started to pull them apart a little more. She leaned in and kissed my buns as she massaged. Ever so gently, she was kissing closer and closer to the center. Her tongue swipped across my butthole. That sent a shiver up me ( in a good way). She then began to draw cirles around my hole with her tonugue. I was in another world.
She worked her tongue right into the opening and all around the sides.
After the longest time, she went back to kissing my buns and asked me to roll over. I flipped onto my back with one long and very hard cock sticking straight up. She pulled my ballls up and licked my butt again. She worked her way up the ‘taint to my balls. She did her magic on them. Up along the shaft then swallowing the whole thing. She worked her mouth on my cock and coming around back, she slid a finger up my ass. It wiggled. With her lips on my cock and finger up my backside, I blew my load.
What a nice woman.
On another weekend, we wanted to try anal (on her). She said Mike tried to shove his cock in her ass once but it did not get too far. Well, shoving it is not the way to go. I said we could do some preparations to make it better and easier on her. In reality, the prep was more for her mind. A couple days before, she changed her diet. I gave her a menu to follow. Need to have the system cleaned out. The day before she took some stool softeners. On Saturday morning she took an enema. My evil little girl had her husband helping her. She told him all about me getting her ready to take it up her ass. Something he could never pulll off. Just before coming over, she took a long hot shower. She had Mike get her good and clean down there. He was washing her butthole for me.
By the time she came over, she was so hot to try it. She could not wait. I adjusted my plans for an evening go at it. I wanted to take her out for a nice evening first. Maybe a little romance. But she was not waiting any longer. She spent the past few days just dreaming of this. She was ready now! I made a small lunch for us and poured her a glass of wine. Something to take the edge off.
She had her sandwich and two glasses of Malbec. Then up to my room carrying a fresh third glass.
We got naked and she layed down on the bed. On her back and she closed her eyes. I started gently rubbing her face, down to her neck, boobs, tummy. I worked a few fingers in her twat. She was hot and wet. I rubbed her thighs.
I rolled her onto her belly. The room was heating up with anticipation. I rubbed her neck and down her back. I got slower as I got to her buns. I gave those nice things a good massage. Then I pulled them apart. Exposing the rosebud. She let out a soft moan and said “oh ya”. I reached under and stuck my fingers in her cunt again. Still hot and even wetter. Then I moved my wet fingers and traced circles around her butthole. Then my finger went right on her butthole and I applied a little bit of pressure. I got down and began to kiss and rub her buns. My kisses got closer and closer to the hole. My tongue traced circles around her hole just like my finger did a few minutes before. My tongue reached her hole. She pressed back into me. I had one hell of a hard on. I went to town tonguing her asshole.
I came up for air. I sat on her thighs and rested my cock on her crack. It’s amazing that there are somedays that your cock just seems to swell up more than others. This was one of those days.
Fucking A.
I got out the warming gel oil. I already had it warmed up. I put some on her upper back and worked it in. Getting her neck and working on down her back. I slid down and my cock now rested between her thighs. I got lower on her back and then to her buns. I worked the oil in. Then….. I poured a lot of it right on her crack. I pulled the buns apart and the oil ran down acros her butthole. I took my finger and rubbed it around the hole. Pouring some more oil on, I worked one finger inside. I raised her ass up and let out a louder moan. Working my finger in past the knuckle and moving it in and out. I the stretched it a little and ever so gently worked two fingers. I began to move them in and out a little faster. I poured more oil on. She was well lubricated and opening up. I stopped with both fingers all the way in. I leaned up presing my chest on her well oiled back and wispered in her ear “are you ready”. She responed with “take me please”. I pulled my fingers out and sat up. She sat up a bit and took a big sip(gulp) of her wine.
I rubbed a generous amount of oil on my cock For kicks I oiled my balls. Just because. She brought her knees under her and was on all fours. That ass was looking right at me. I spread those cheeks and layed my swollen cock at her asshole. I pressed the head in. She yelled” oh Goddddd. Yessssss”. I held it for a second. Then pulled out to work it back in again. I kept pulling out and going back in a little deeper each time. Finally, my cock was burried all the way in her asshole with my well oiled balls pressed against her. I wrapped my arms around her belly and whispered in her ear “I love you”. I guess nothing says I love you more.
She responded with” I love you too. Now just fuck my ass”.
I was moving in and out. Faster and faster. I was going full speed on the well oiled ass. She was howling. I was holding those hips and moving her in a good rythm. What a beautiful sight. Watching my cock ride in and out of her butthole. A nice fit. She was frigging her clit and yelling like we were the only two people on earth. The mouth on that woman. I loved it.
She seemed to have had an orgasm and I slowed down. Pulling out, she flipped on her back. I placed a pillow under her and she pulled her legs way back. That ass was callimg me. I put some more oil on my cock and went back in. No slow start. I just pounded that ass. Holding her legs up just under her knees I fucked her. She was ramming fingers in and out of her pussy. She came again. I pulled out. She stood up on the side of the bed and bent over with her belly on the bed. Flairing her ass up. I stood behind her and just slide my cock back in. I told Jocelyn I was almost ready. We were going at it and short time and I felt it coming up. I told her to get ready. Pushing and pulling on her hips, I shoved my cock all the way in and squirted. A few more deep thrusts and she had an ass full of my hot cum. Holding it all the way in I paused and held her. We both were enjoying the moment.
I pulled out and we both layed on the bed. Holding each other in that post bliss. Her ass leaking and enjoying the experience.
After a long while, we got up.
I looked at the bed. Those sheets were done. More business for Bed Bath and Beyond.
She asked if she could call Mike. When she got him on the phone, she let him know her ass was well fucked and full of cum. Mike said he knew – he said we should have closed the windows.
We took a nice long shower. Still on our robes, we sat in the kitchen with a cup of afternoon coffee. Later, we got dressed and went to dinner. Relaxing and recovering.
Back the house we went to bed in my guest room. None of us felt like changing the sheets. As we curled up naked, Jocelyn slide down and gave me a very nice and relaxing blowjob.
The next morning we went to Dobbs Diner again for eggs Benedict.
Upon return the the guest room, Jocelyn wanted to do it again. She got on all fours and I oiled us up. What a sight. Her on all fours, face down into the pillows, her asshole looking up at me, cunt lips hanging down. Easier this time, I just fucked her rosebud. I grabbed those hips and pulled her open even more. Staying in this position, we went at it and I eventually shot my load. Again she was fingering herself and got pretty loud. I had closed the windows.
With my cum in her ass, she put her panties and threw on a sundress. No bra. At noon, she walked back to her house barefoot. Mike and Emma were outside by tne front door as usual. Jocelyn kissed Mike and then turned to Emma. With her back to Mike she leaned over to kiss Emma and stuck her ass up at him. They went inside. later,Jocelyn said Mike took her to the shower and washed my cum off her ass and legs.
In other parts of our routine, I had to set the limits. Jocelyn tried to get sexy on some texts. I dont play that game. Text for practical matters only. You will never get a dick pic from me and if I want to see your pussy, I’ll call you over.
The other limit is we only meet on Saturday for intimate time. Jocelyn came over one Wednesday for a chat. I am all good for that. Then she tried to suck my cock. I had to push her away. Control. I need to maintain control that we only play on our set time on the weekend. I have my business to attend to. It is what keeps both households going. Beside, her cocksucking on the weekends is satisfying enough.
And its my house. She has her closet; the rest belongs to me. No decorating, moving things around or bringing over her pictures to hang.
Chapter 4: July 4th weekend
The strangest weekend of my life (so far).
One day during the week, Jocelyn came to see me. She wanted to know how to deal with the upcoming July 4th. Since before Emma, her parents, Steph and Sal, would join them for a July 4th cookout. It was a big deal for her parents. But this year, it fell on a Saturday. How do we handle this she asked.
The quickest most well played response I have ever worked up. Normally, I prefer to ponder what the response will be then work on the delivery.
I had to lead her to the right path.
I asked her how she felt about our time together. How does she feel she is being treated. She replied that she cherishes our time and looks forward to it all week. Then I asked if I was livivng up to my end of the bargin. She replied that I have been more than generous. She commented on how well she has been taken care of. The new clothes and accessories make her feel special. She has been getting more looks lately. And the family stress is gone since the bills are getting paid.
I let her ramble for a bit. All the good stuff flowed out.
Then I mentioned that to keep this going we must stick to the basics of the deal. She belongs to me for those 24 hours. The other day she is Mike’s. I let her know that I cared very much to keep this arraingement. It has meant so much to me.
I suggested that she and Mike host the cookout like they normally do. Invite her parents and dont bring any extras this year. I will buy some of the best steaks, lobster and all the side dishes. I will stock Mike’s bar to the fullest. Something that has not been done since they arrived.
Her parents normally come by before noon. I said I would arrive at noon, and then she treat me like her husband for the alotted 24 hours. I said just let the situation flow and go with it. Have a talk with Emma before just to reinforce that her and I have special times together on the weekend.
She agreed and the events began to unfold.
I ordered the food to be delivered. I stocked the bar.
Around 10am on July 4th, I saw her parents, Sal and Steph, pull in. At noon I walked through the front door. It’s noon and I now am the master of this house.
Emma came running up and gave me a hug. Jocelyn walked into the foyer and tried to give me a peck on the cheek. I brought her into my arms and slowly gave her a more intimate kiss. I looked up and saw Steph staring. I broke contact with Jocelyn and walked over to shake Steph’s hand and gave her a hug. We all walked out back to greet Mike and Sal. They were warming up the grill. Steak for lunch.
I sat in a lounge chair and Jocelyn brought me a beer. She was wearing a very thin sun dress. Anyone could tell she was wearing a bra and panties. Once I had my beer going, she brought out some snacks of shrimp and some mushrooms. We all started jabbering about life. Jocelyn was very attentive to me.
Complements flowed. I kept saying how lucky I was to have them as neighbors. They mentioned how well I look after them. Mike let her parents know I had all the food and drinks sent over. Even Emma had something to say. When Jocelyn brought me my second beer, Emma said how her mom and I make such a good couple on the weekends. That raised and eyebrow from Steph. Emma went on to say how her mom looks forward to her special time with Joe every weekend.
With that comment, the steaks were ready. Mike is pretty damn good on the grill. We had a fanastic meal. After lunch, I was stuffed. I sat back on the lounge chair. What a great afternoon. I fell asleep as the others chatted and cleaned up. I woke up with Jocelyn rubbing my feet. I really like when she does that.
When I was fully awake, she got up and sat on the side of my chair. It was a rather warm summer day. I softly said to her she would be more comfortable if she took off that bra and panties. She left to go in the house and returned as she should be dressed. Now it was rather clear that she had no bra and panties. Her nips were very visible. When the light hit it just right, you could see her pussy patch and buns. She was hot.
We all spent the afternoon playing yard games like badmitton and bocci ball. Watching Jocelyn run around in that sundress was worth the price of admission. Sometime after 6 pm Mike started getting the lobsters ready. By now Jocelyn had clearly established that I was the focus of her attention. She would hold my hand, give little hugs and kisses, rub my sholders. Not once paying any mind to Mike. Just as she should. As Mike got dinner ready, Jocelyn sat next to me on the lounge chair. I put my arm around her and gave her a passionate kiss. Right in front of her parents, husband and child. The converstaions stopped. I pulled her in tight. Emma broke the silence by saying we made such a cute couple.
With that comment, Jocelyn hugged me tight and kissed me deeper. She let go of our lip lock and started to kiss my neck. She then looked up at the others and said how much she loved having me be around. I had a boner. Wearing a pair of loose fitting LLBean nylon shorts, I sort of showed.
Jocelyn stopped kissing me but held on tightly. I had my arm around her waist and brought it up to just under her boobs. In fact, my arm was pushing up on them. It was obvious to all on the porch. Jocyeln finsihed a gin and tonic and became more relaxed. I moved my hand from under her boobs down to resting one hand right on her thigh. I pulled the sundress up to do this. The looks from Steph were priceless. I am not sure what Sal was thinking – but then again I did not give a crap about him.
The lobsters were ready. I stood up with a raging boner. Emma blurted out that Joe must be liking her mom. Sometimes you just don’t care. We sat at the table. Jocelyn moved her chair against mine. She orderd Mike to bring us our food as the others went through the serving line. As we ate, Jocelyn cracked open my lobsters and fed them to me. I licked the butter off he fingers. At the end of the meal, she took a wet wipe and cleaned me up. She looked at my crotch and said aloud that there was butter there. She cleaned my lap with the others looking on. There was no butter.
Jocelyn and I took my boner back to the lounge chair. The others worked on cleaning up while I had another beer and Jocelyn had a gin. After clean up, Mike and Sal started a fire in the chiminea. I sat with Jocelyn on my side. My hand moved up near her tit. I was lost as to what the converstaion was about. My hand made it to her nipple. I was rubbing her boobs on the outside of her dress. In a swift motion, I just moved my hand under her dress to rub her tit with no barrier. Now the conversation slowed again as the show between Jocelyn and I became the focus. No words discussed what was happening, it just flowed.
After the longest time, Jocelyn just moved my hand to her crotch. Fuck. I was rubbing her cunt in front of her family. The dress covered the actual deed, but everyone could see what was happening. Steph did not know what to think. Mike was enjoying the show.
Steph broke the ice by asking if Jocelyn and I were always this close. Emma quickly answered that Joe and her mom had special time with each other every weekend. She said it in such a way it was cute.
Jocelyn moved to straddle me. She was now facing me with her legs spread on my lap. Her dress was pulled up so that her bare pussy rested on my boner. The dress was drapped in a way so that nothing was visible. Only my thin nylon shorts seperated us. She grinded a little. Her arms wrappped around my neck.
This was getting a little too much even for me. I spoke up and told Sal he needed to bring Emma inside. Time for grandpa to read her some stories and get her ready for bed. Emma objected but somehow I convinced her to go.
Once they left, Jocelyn said we need to fix this. She reached under her dress and opened my shorts. My cock was free and against her pussy. Not quite comfortable , I just slid the damn shorts off. Now Jocelyn straddled me with not much left for her mom and husband to guess. She grabbed my cock and put it into a very wet pussy. She just sat on it and gave me a kiss. We were making out with my cock just resting inside her.
Then…. She started to slowly ride up and down. I looked over at Steph and Mike. They were mezmerized. Jocelyn picked a nice slow rythm and kept it steady. Her hands alternated between rubbing my head and my neck. Her eyes were closed and she was lost in her fantisy. After about 15 or 20 minutes I was getting close. Wanting to keep going, I had to make a distraction. I held Jocelyn to stop. I looked at Steph and told her to get me another beer. As she brought me a beer, I had an evil thought. I moved my hand under Jocelyn’s sundress and wiped my hand across her sloppy cunt. When Steph handed me the beer I took it with my wet hand and made sure it rubbed across her hand. She looked at the wetness on her hand, smiled and sat down.
I took a swig of my beer and signaled Jocelyn to continue. Now she moved with some gusto. She put hip movement into her swing. She was soon riding my cock like there was no tomorrow. The sundress hid nothing. Steph sat almost directly in front of us. She had a nice view of her daughters pussy riding my cock. Juices flowed. Jocelyn was grunting. I pulled part of her strap aside so a tit cold pop out. She let the other one sneak out.
Another 15 to 20 minutes that feeling came up. I was ready to exploded. I pushed my hips up to meet her as it came. That wonderful moment. I held onto her hips as I filled that cunt. What a nice cunt. Doing what it should be doing. Sucking up my sperm.
Once I stpped ejaculating, Jocelyn just rested with me buried inside her. I asked Mike to bring her a fresh drink. She sipped her gin as we enjoyed the bliss. Soon my little guy wanted to pop out. Jocelyn told Mike to bring her a washcloth. He handed her one as she stood up. I could see drips going down her legs as she tried to wipe. Mike had a second washcloth and helped.
My fat wet cock glisened in the deck lights. My balls were wet. Steph’s eyes were glued. I wanted to tell her my eyes were up here; but somehow I understood her need to look.
Jocelyn tucked her boobs back in and picked up a blanket. Knelling before me, she drapped the blanket over me and was underneath. She worked on cleaning me up. In the most gentle way, she licked her juices and my cum off my cock and balls. Her mom and husband could hear her and see the blanket moving. I felt like a king.
Mike was rolling both washclothes in his hand. I asked Steph if she wanted one. She took one from Mike and shoved it down her pants. Somebody must be wet down there.
After Jocelyn cleaned me up, she put my shorts back on me. We sat around the chiminea. Jocelyn was in my arms. I asked Steph if she liked the show. She came right out and said it turned her on; different and maybe wrong, but still a turn on. Mike was still sporting a boner.
Sal returned, having put Emma to bed.
Steph was the first to speak. She told Sal he missed a very romantic encounter. She said Sal needed to do some romancing when they go to their room. Sal mentioned that it looks like Joe and Jocelyn didn’t wait for a room.
I tried to disfuse the conversation, as I just was not in a mode to discuss it. Your daughter/wife just fucked me and it was nice. Now just let me have my after dinner/sex scotch.
Mike brought me some Oban. Neat and a double.
After chilling around the chiminea the evening was over for me. My original plan was to just take Jocelyn back over to my place. I seized an opportunity.
I stood up and held Jocelyn’s hand. I announced we were going to her room to spend the night. Mike would get the couch as the guest room was occupied. Jocelyn lead me up to her room. Without much effort, we got naked, tucked under the sheets and off to a sound slumber.
Jesus loves me.
The next morning I awoke with Jocelyn fondling by balls. I rubbed her boobies back. I suggested we take a shower and fuck. She did not argue. We went into her master bath. She was able to get me a new toothbrush and razor. We took a long shower. Every nook and cranny got cleaned twice or more.
All fresh, we got naked back under the sheets. We started with me on top for 69. I just love going down on my Jocelyn. She just smells nice. She did a pretty good job on sucking my balls and licking the ‘taint. I rolled her over and put her on all fours. I spread those butt cheeks and entered her pussy.
For some reason I looked up and saw she opened the door.
I fucked and slammed her. My bitch. I could fuck her in this position a 100 times and the 101st would be just as nice. I grabbed her hair and she started getting loud. I did not expect her to go into her howling with a house full. Even after last night.
I ran a finger aound her butthole and tickled it. She almost instently changed pitch. She screamed for me to fuck her ass. She was a different woman. Possesed. She screamed again in a high pitch to get my cock working her asshole. Like she would die if I didn’t. My cock was well wet from her pussy. In it went.i tried to go slow but she started slamming back into me. Good Lord. I fucked her ass and pulled her hair. She was yelling for me to fill her ass with my cum. She wanted to feel it inside her. She wanted it dripping back out. I came. She yelled some obsenities. Lenny Bruce would be proud.
I pulled out and we both moved to sit up in the bed. I was just guessing at the puddle she was sitting on. We hugged and kissed as a way of saying thank you to each other. I love tasting her pussy and fucking that asshole.
Once we recovered, she said we need coffee. She called for Mike, in a voice lower than her passion, and he came in. He was flustered and hard. Jocelyn was sitting up and her boobs were on display. She told Mike to get us some coffee. When he delivered, she ordered our eggs and bacon. As we sipped our coffee we could hear him making breakfast and talking to Emma. The two of them served us, with Jocelyn still sitting up. Emma was staring at her moms titties. Jocelyn did a good job and explained how it was ok to be like this when you’re with family and close friends. But not polite to stare. Emma was good about it and moved on to ask what their plans were for this afternoon.
After breakfast was cleared and Mike and Emma were back downstairs, we took another shower. There was one nice stain on Mike’s bed for him to clean up later.
Aftr the shower, I had no clean clothes to get in. Jocelyn had to run next door while I watched the news in the nude.
All of us were downstairs for a late morning coffee. Around 10 I took Jocelyn back to my place. I almost went home and left her, but she is mine until noon. Before we left, I told Steph to go change the sheets, wash my clothes and bring them to me.
Jocelyn left right at noon.
Around 2pm, Steph knocked on my door. She had my clothes washed and folded. As she should. I invited her in. Alone now, I asked her how her weekend was going? She said it was interesting. I told her that I enjoyed fucking her daugnter with her watching. I love what Jocelyn can do to my cock. Curious, I wonderd how far I could push my luck here. I told her to take her shirt off. She did, and even took her bra off. I gave her some good complements. The apple does not fall far from this tree. Steph had a nice body. I told her to drop her drawers. He took her sandles off, and her pants, and her undies. Steph was all nude in front of me. Nice. Very nice. She turned around for me to see her ass. Well formed. Facing each other, I walked up to her and reached around for her buns A quick squeeze and then I moved my hand to cup her pussy. I worked my thumb up inside her. She smiled. I asked If Sal fucked her last night. She said he did not get it up. A usual occurance. I said too bad. I got it up for her daughter and we fucked. I told her how I fucked her daughters ass this morning. She laughed and said that was no secret. She tried to reach for my cock but I pulled away. I was well satisfied, but I did get a boner. I told her about our agreement between Mike, Jocelyn and I.
Steph said she understood. She got dressed and I walked her to the door. I had four weeks to work on something here.
And that was the end of the first phase of my period with Jocelyn.
