Elaine's First Time

Aug 2, 2019
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I have shared my wife with many men over the last 30 years. This is how we started, kind of mild compared to some of the wilder stuff we did later,

We are in our 60s. I met Elaine when I was 32 and she was 29. We were both divorced with no kids. After dating for several months I really started liking her. I had done some swinging and wife sharing with my ex wife. I don't think that led to our divorce, but one never knows. I got Elaine to pose for sexy polaroid pics and she didn't seem to object like some women do. For my birthday she surprised me with some lingerie photos done by a professional she had hired. I was more than pleased with that attitude. After about a year I decided to broach the idea of sharing her. Started with sex talk in the bedroom. While having sex she acted willing saying it might be fun, but nothing ever actually happened. I knew for our relationship to go further I was going to have to press the issue to see if she ! was all talk and no action. I kept telling her to pick out some guy she would like to fuck. I didn't care if it was old lover or friend. She said she could not approach someone about having sex with them if she really loved me.

I thought a random stranger might work. This was in the early 80s before internet. I had been to the local adult bookstore and seen personal ads so I posted one. Phone numbers were not allowed. If you wanted to respond to an ad you left your information on a 3x5 card in an envelope with the number of the ad you were answering. You had to personally go to the bookstore to check. I talked Elaine into going with me one night. After checking the ad board we walked around the store. I tried to get her to go into the movie theater section but she declined. While wandering thru the store a nice looking well dressed older gentleman approached us and asked if we were looking for fun. I said maybe, depending on what he meant by fun. He suggested we go outside to discuss the situation. Elaine was hesitant but followed. To our surprise the guy had a real nice luxury car.

He invited us to go for a ride in his car. I can't really think of what line he used, but we were young, dumb and horny. I sat in the front seat with Elaine in between us. She was wearing a short skirt and let him put his hand on her leg. I wasn't sure where we were going nor what was going to happen, but Elaine told him she felt uncomfortable. He assured her he was not going to do anything she did not like. He just wanted to touch her a little and watch us fuck.

We finally found a secluded place to park behind some closed store building that had security lights. He situated the car where the light shone into the window enough to let him see what was going on. I could tell Elaine was still somewhat nervous and I said we would leave whenever she wanted and the driver agreed. While still sitting between us Elaine reached down and slid off her panties leaving her pussy somewhat revealed. At this point in our relationship she had never taken things this far. We were not married, but I was living with her. She let me take photos of her and we engaged in sex talk about introducing others into our sex lives, but talk was as far as we had gone. I was almost as nervous as she appeared to be, but anxious to see where this evening was going to end.

She leaned over and kissed me leaving her ass and pussy exposed to the driver. He slowly massaged her ass as I continued making out with Elaine like a teenager. I started feeling her up and he finally got the courage to move is hand to her pussy. I thought she might object but she let him play with her cunt as I played with her tits. She reached down and unbuckled my pants, pulling out my cock. After fondling me for awhile she repositioned herself on her knees, sideways in the front seat with her head and mouth on my cock and her pussy eye level to the driver. He started playing with her ass again gently massaging her butt cheeks. It looked like he slid a finger inside her. I thought she might object but she just kept sucking me letting him have full access to her pussy. He got braver using both hands, slowly spreading her cheeks and licking her pussy. I thought maybe we were going to experience our first MMF sex intercourse.

Elaine instead moved over and sat on top of me facing the front and lowered her pussy onto my cock. I had pulled her top up over her boobs and she left them out of her top while grinding on me. The driver moved closer to us and reached for Elaine's tit. She didn't object, but did tell him all he could do was touch. He said fine, but could he touch himself. Elaine said okay but he was not going to screw her. Surprisingly he did not seem to care. I was curious how this was going to end.

After playing with her boobs he slowly moved his hand toward her crotch and I wondered what was going to happen next. We had been screwing with my legs apart and her leg somewhat together kind of doggy style while sitting in a car seat. She told the driver to wait a minute and I thought the party may be ending. Instead she got off me momentarily, pushed my legs together the placed her legs outside of mine and sat back on my cock. Then Elaine took his hand and guided it to her crotch. It was kind of weird but she seemed to enjoy the extra stimulation of him fingering her clit and pussy lips as my cock was in her at the same time. I could kind of feel him manipulating her pussy clitView attachment 86296View attachment 86297View attachment 86298 but she just continued grinding on my dick. After a few minutes Elaine said it was time to switch and I thought she was going to fuck the driver.

Instead she turned around facing me and straddling my cock with her knees bent under her. The driver was playing with her boobs and pulling his own cock. I guess she felt sorry for him because she leaned back and pulled his face to her tits allowing him to kiss her nipples. With this action she started cumming hard causing me to shoot off inside her warm pussy. When I finished I glanced over to the driver and he had shot off and was cleaning himself with a hankie. I kind of felt sorry for him, but all he could do was thank us and tell Elaine how pretty and sexy she was.

I knew then I had a special lady. We all got dressed and he drove us back to the bookstore. Never saw him again. Certainly not the wildest sex story, but memorable to me because it was the first time Elaine had allowed another man to play with her while we were fucking.

The irony of the encounter at the bookstore was that it almost backfired for me and my plans for Elaine and future fun. She admitted she actually enjoyed the sex but not the atmosphere at the bookstore. While it was erotic it was also scary for her. The gentleman in the car told us he was there on Saturday night it we wanted to meet again, but we never did. It was her refusal to return there that cause me to come up with another angle. I had to find a guy she felt comfortable and in a setting she liked.
Damn she is so yummy and I bet she tastes so good to be eating
 
Aug 2, 2019
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We went to a friend's wedding reception in St. Louis, about a 4 hour drive for us. The groom was the son of a friend. We knew we would be drinking and partying so we booked a room. We had nothing specific planned, but when we were out of town we were always open to something interesting that might arise.

The reception was pretty good with great food, booze and dancing. There was a young single guy named Tom at our table that we didn't know. It was very obvious he wanted to dance but it seemed he did not know anyone there other than the bride and groom and a few buddies. He was a nice looking guy about thenty three or twenty four and seemed very polite. I told Elaine that she could ask him to dance if she wanted. We started small talk with him, learning that he was on leave from the U.S. Navy and was home for his friend's wedding.

A song came on that Elaine loves and she asked Tom if he'd like to dance. He quickly looked at me and I nodded that it was OK with me. When they came back to the table he thanked me for letting him dance with my wife. I told him he could dance with her anytime as I wasn't into dancing very much. As the night wore on, they danced quite a bit.

I happened noticed a couple times that he had a hand resting on Elaine's ass while slow dancing. It seemed he was having a great time dancing with her and chatting with us. I mentioned to Elaine that I thought he might be interested in a little more than just dancing and chatting with her. Elaine had dressed conservatively for the wedding so I suggested she go the bathroom and pull off the bra and panties. She declined saying she thought he liked her already since she could feel his hard cock pressing against her on the slow dances. She also said that if she was even close to being correct, he had a very nice size cock. I asked her if he had tried to hit on her. She said no, but he tried to cop a feel of her ass and tits whenever he could without being blatant about it.

A little later in the evening, he said he was going to his room for the night. We asked him if he was staying at the hotel and he said he was and mentioned his room number. It happened to be down the hall from our room. We told him we had to stay a bit longer and visit with the father of the groom and said good night to him saying that it was nice meeting him and maybe we could talk later. We continued sipping our drinks and chatting with our host for another half hour or so before deciding to call it a night ourselves.

On the way up, Elaine mentioned that the young man seemed to be very nice. I asked her if this meant that she was sorry we allowed him to get away from our company. She smiled and said she was a little interested in finding out more about him. I think she was a lot more interested in investigating that hard cock she had felt while slow dancing.

I asked if she would like have sex with Tom. She said he was awfully young and might think she was too old. I just looked at her and said I am sure you can convince him to try an old lady. She smiled and asked me to call and invite him over for a nightcap. Prior to calling, I asked her to change into a short mini skirt and put on a sweater with her shelf bra and some hose and garters minus panties. As it was the Christmas holidays she had an attractive red skirt and sweater with a light weight jacket. When she took it off the it allowed her nipples to protrude through the holes in the sweater fabric. I then called. The phone was answered immediately. I think he was hoping that we might call him as he readily agreed to come over.
0tasty hood baby
 
Aug 2, 2019
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Part 2

By now my cock was getting hard so I took my clothes off, sat back down and began to stroke my cock as I watched my wife suck his cock. Mic then laid Elaine back and got between her legs and guided his dick to the entrance of her hot cunt. Laying down on her pressing his lips to hers and mashing her tits against his chest Mic slowly pushed his cock into her. I watched as Mic's cock slid into Elaine inch by inch. Her groans were very evident as Mic began to fuck her. Raising up just a bit now Mic began to quicken his pace sliding his cock in an out of her faster and deeper. "Damn you sure do feel great" Mic said. Elaine's's eyes rolled to the back of her head as she smiled "So do you". Mic then raised up even higher and placed his hands on her tits as he fucked her. "Fucking nice tits baby" he said as he continued to pound her with his cock. Mic paused very briefly from time to time to lean down and suck her tits. He then placed her legs up over his shoulders and drove his cock deep into her. I knew then it would not be long before my wife would cream Mic's hard cock. Elaine loves to be fucked this way. She had told me that she loves it cause the guys cock gets so deep into, and it makes her cum every time. Sure enough she did just that.

My wife's face turned a deep read as she gasped deeply. Clutching the bed sheets with both fists her body stiffened and then she let our a shrill squeal " oh fuck, oh fuck, oh fuck". Her ass was up off the bed and taking in all of Mic's cock she could. Elaine began to gyrate her ass up and down engulfing a much of Mic's cock as she could as her hot cunt spasmed with orgasmic pleasure. "That's it baby fuck my cock, cover it with your juice!". A big smile came over his face as he held his cock deep into my wife as he could. Feeling her warm juice on his cock, he nodded "yes yes, mmm so nice". He suddenly quickened his pace, grunted and moaned as he filled her pussy with his first load of cum. I thought he would roll of her giving me a chance at sloppy seconds, but he did not.

Instead he pulled out his cock and laid back on the bed and told my wife to sit on his face. I want to lick and taste your freshly fucked pussy and lap up all of your cum. I could not believe it. Watching someone lick Elaine's cum filled pussy was becoming one of my favorite sex acts. Elaine seemed to enjoy it too and spread her legs ( her breathing still rapid from the intense orgasm) lowering her full pussy down on to Mic's face. He darted his tongue over her swollen clit and began to lap at her pussy lips taking in her and his own cum. Elaine sat upright pressing her cunt down onto Mic face so his tongue could penetrate her and let the cum would flow onto his face. Looking at me she winked and began to cup and play with her tits. Elaine then bent down a bit and took Mic's cock into her mouth and began to suck and lick his cock clean of her juice. Not wanting to let Mic have all the fun I got up and put my cock in front of my wife. She took the hint and began to suck me as well. "Oh fuck" I mumbled out looking down at Elaine sucking my cock and then moving her mouth to Mic's cock. Am still not sure how the hell I kept from cumming. I normally am in on the action a little earlier than this but I was having a blast watching Elaine trying to make this a fuck session Mic would never forget. I guess Mic liked eating creampies while Elaine was eating him as his cock was getting hard again.

Mic then told my wife to sit on his cock and ride him. Elaine got up and turned around and faced Mic as she lowered her cunt down onto his cock talking in all of his erect cock she then began to slowly move up and down riding Mic's erection. "Oh yea baby that's it, fucking ride me. Fuck me baby fuck me" he grunted. Each time my wife drove her cunt down onto Mic's cock he would raise up and push his cock deeper into her. I had moved around to the side to get a better look at her tits bounce and sway as she rode him. Elaine was looking right into my eyes as though to say "Do you like watching me fucking his cock". Mic reached up and cupped my wife's tits and began to massage then and tweak her erect hard nipples. Looking over at me he said "Damn, your wife is a great fuck"! Elaine looked Mic in the eye said "Well if you like my pussy I'll bet your really gonna like this". She raised up and took Mic's cock out of her pussy and guided it to her ass hole. My wife then very slowly lowered her ass down on to Mic's cock. She took the head inside her butt and paused letting her rectum slowly relax. Inch by inch Mic's cock penetrated my wife's ass. Mic groaned loudly as his cock was engulfed by Elaine's ass hole. "Oh mother fuck", YES YES, your ass is so fucking tight". By now I am wanting to cum , but I also wanted to hold off a bit and get some of that nice pussy and ass as well. Elaine rode Mic's cock for a bit longer and then Mic said " Lets DP her". I looked at Elaine and she nodded approval taking Mic's cock out of her ass and guiding it to her pussy. Once Mic had his cock in my wife's very wet pussy, she bent over and allowed me good access to her ass. We got a pretty good ryhthm going and I was about to cum when Mic said the one thing he had never done was to fuck a woman's pussy with another guy fucking her pussy at the same time. I waited for Elaine's response. She said "Go for it". Getting on the bed behind her I guided my cock into her already occupied pussy. Sliding my cock over Mic's cock and into her pussy I was hoping we could both stay in her. "Oh fuck" my wife gasped as the two of us began to fuck her pussy at the same time, alternating our in and out strokes. We all three lasted longer than I anticipated, but soon Elaine was squealing with delight and started to cum on both our cocks. " FUCK ME YES YES FUCK ME!" she yelled. That pretty did it for me and Mic as well as both of us began to add both our loads of cum with hers. Mic and I both grunted and shot good size loads of cum into her. The three of us then collapsed onto the bed. It had to be one of the wildest sex experiences I have ever enjoyed.

Mic showered, told us we could have the room for the night as he had to get home and hoped we could get together again. Elaine never returned his phones calls. I guess she got revenge, but we all had fun. photos are the little dress she wore to the reunionView attachment 87301View attachment 87302View attachment 87303
Sweet and yummy
 
Aug 2, 2019
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After Elaine had a little success approaching men on her own she gained confidence. I encouraged her to use her womanly charms to entice men to have sex with us. She was hesitant at times for fear of rejection. Elaine had married her high school sweetheart when she was 18. I think maybe the fact that she really only dated one guy in high school and was married through her college years made her somewhat shy about flirting and dating. Who knows, but I wanted her to assert herself and told her she should not be coy about what she was after with the other man. I told her that after bringing up the subject of having sex with the guy I thought she probably tended to talk too much. I said I did not want her screwing them without me being present, but kissing, fondling and even giving a blowjob would surely convince the guys to party with us.

One afternoon she came home from the grocery store and said she thought one of the young guys working at the store was trying to flirt with her. I asked her if she would consider doing him and she laughed and said he was awfully young and probably just being polite to an old lady. I said she should fix herself up a little, go back to the store and flirt back. As it was winter she put on a sweater without a bra, slacks and jacket. When she opened the jacket the sweater gave you a good view of her boobs. Elaine walked around until she found the checkout line he was working. As they always do he asked her if she needed help carrying out her groceries. Even though it was just one bag she said yes. While walking to the car she asked him if he had ever partied with older women. He said no and she asked would he like to. He said he had to get back to work but his shift ended in an hour and would like to talk to her then. She said she would be back and park in the same place. She came home and told me what had happened. I suggested she bring him to our house as the store is less than a mile away and she could be more convincing in our driveway rather than a public parking lot.

When they arrived Elaine pulled the car close to the garage door which had a row of windows in it. I told her I would be watching from inside the garage. I could see them talking and watched Elaine slowly move closer to him. After a few minutes she kissed him and I figured things were going well. Knowing I was viewing them she moved his hand to her chest as they continued kissing. My view was partially blocked but her hand appeared to be on his crotch. Soon her head lowered and I could just see the top of her hair as she apparently moved her mouth up and down on his cock. I saw him say something to her and reach down putting his hand on her head. I really did not know if he was moving her head away or what exactly was going on, but her head popped up and she was smiling as she kissed his cheek. I could see them getting their clothes arranged and I quickly moved from the garage to the house and met them at the front door.

They walked in and Elaine introduced me. His name was Steve and he seemed very nervous. I invited him in the living room and asked if he wanted something to eat or drink. He said sure and Elaine went into the kitchen. He asked where the bathroom was and I went into the kitchen with Elaine. She almost started laughing when she told what went on in the car. She said she had only sucked his dick for less than a minute before he yelled he was going to cum. She held on tight with her mouth as he shot a load of sperm into her waiting lips. She guessed he had not had sex for quite some time, but thought he was going to be more than ready for a fun evening.

Steve was back in the living room when we walked in with munchies and drinks. I asked if he wanted wine, beer or a soft drink. He said he was only 19 and still lived with his parents so had better stick with non alcohol drinks. He had just graduated from the same high school Elaine and I had gone to years earlier. We chit chatted for awhile and I could tell he was anxious and getting nervous about everything. I knew Elaine had told him about me and the three of us having sex together, but thought he might be getting cold feet. I smiled at him and asked if he thought Elaine was a good cock sucker. We all laughed and the ice was broken. Elaine stood up, walked over, stood in front of him, lowered her slacks revealing her pussy and pulled his face into her crotch. He was just kind of stunned and Elaine told him to lick her, which he happily did. Elaine teased and played with both of us but said the living room was cold and we headed to the bedroom.

We got in bed with Elaine in the middle. We played with her as she sucked and played with both of us. I licked her while she sucked him. After she sucked him back to hardness she pushed him on his back and straddled his young swollen dick. Elaine was just getting going pretty good, grinding away on him as he tweaked her tits when he suddenly grabbed her ass and shot his load deep in her pussy. We were both kind of shocked as I knew she had just finished him off with her mouth 20 minutes earlier. I joked that he must have not had any pussy in a long time when he started laughing and said he had never had any pussy. Elaine did not believe him, but he said he had never gotten any girls to go all the way with him. She finally said that explained why he shot off so fast in her mouth and almost as fast in her pussy. Elaine said she would fuck me for awhile and see if he could recover for a third time. He said not to worry he wanted to fuck her all night.

Steve was a very willing participant, but not highly skilled. When Elaine was sitting on me he was happy to just be touching her, playing with her ass, back, any skin he could find. Once Elaine and I had both climaxed the atmosphere was very relaxed. Steve did not really know what to do he just knew he wanted more of Elaine's pussy. I couldn't tell if Elaine was annoyed with him or just could not believe she had fucked a 19 year old virgin. I suggested Elaine give him a lesson in sexual positions, let Steve find out how many different ways there are to screw a woman. It was both funny and sexy at the same time watching her instructing him on fucking. He had more staying power this round and Elaine finally got warmed up again. He asked her what position she liked and she said sitting on top with her tits getting sucked as she was grinding on a cock. Then she said if she wanted the man to climax she found most guys like doggy style, especially if she gets on all fours with her ass hear the edge of the bed and the man can stand up while grabbing her hips and pounding her pussy. He said let's try it and banged her hard as he shot off one last time. She said she was tired and asked me to drive Steve back to his car. He got dressed and could thanks Elaine enough for taking away his virginityView attachment 86495View attachment 86496View attachment 86497
So yummy makes my cock hard