Elaine's First Time

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
You wife is stunning and your stories are an inspiration
 
  • Like
Reactions: sincity5522
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.
What a night that must have been, I envy you....beautiful woman, sexy and willing to let others into your sex life.....
 
  • Like
Reactions: sincity5522
I have been offline, no internet for 3 days. I did have time to look, but not post old photos I have collected over the years. I actually think I enjoy the first pic a bit more than the second. Watching your wife seduce a young man right in front of you can be hot because you are waiting in anticipation to see how the evening goes. Waiting to join in is good tootumblr_mka4rxHgGf1s331dbo1_500.jpgtumblr_mhaihwsbpj1r3grd2o1_500.jpg
 
Elaine was looking for something in her closet and found a couple drawer full of old lingerie.I teased her about never throwing anything away. Kind of tame but great memories for me. Here is little lace thing she could put on when she did not want to mess with hose, garters, etc. Watching porn and warming herself upIMG_0264.jpglace1.jpglace2.jpglace3.jpgrdil11.jpgrdil12.jpgrdil20.jpgrdil21.jpgrdil22.jpgrdil23.jpgrdil24.jpgriding3.jpg