Elaine's First Time

[Pantherfalcon7]

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 now.. 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 available 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 @@@@@@@ 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 lips 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.

[blackhat1]

Great story, please post some more of your experences .

[Pantherfalcon7]

I agree KJS. That is why I had to make next encounter better.


I was at a business seminar and met a guy through a mutual friend. His name was Eric .We all went our for happy hour drinks and I got him aside and asked him if he wanted to have some fun with my girlfriend. I showed him a polaroid photo of her and explained that I wanted to watch her get fucked and participate at the same time. He was willing and I set up at meet for the following night after our seminar.

When I told Elaine she started getting nervous about how to actually do this as she had never actually screwed more that one man at the same time. I suggested her meeting him at the door in lingerie, but that was way to aggressive for her. Since she had never met him we agreed we would invite him over for drinks and munchies. If she liked him and was willing to try she would invite him to the bedroom. She wanted to start alone with him and see how things went. I told her after some kissing and fondling she should know if it was going to work. If she wanted to back out I suggested she give him a blowjob to completion as a reward for coming over and trying. If she wanted to go through with complete sex she would signal or invite me in the bedroom.

Elaine wore garters and hose, no panties, under a front button summer dress. Everybody seemed to get along when he arrived. Elaine seemed hesitant to ask him to the bedroom. Eric excused himself to use the bathroom and I checked with her to see if she was still up for it and she said yes but just did not know how to bring up the subject. When he came back I simply asked him if he would like to take my lovely girl to bed. He said sure and off they went leaving me nervous and hoping for the best. They left the door partially open and I could hear idle chit chat for a couple of minutes, then the talking stopped. After several more minutes I slowly opened the door to see Elaine on her back and Eric's head buried under her dress. She smiled and waved me in and the party started.

When I walked in the room I got on the bed and started kissing and playing with her boobs while Eric was eating her pussy. We were all still dressed so I started getting undressed. Elaine took off her dress, sat on the edge of the bed and unbuckled Eric's pants, pulled down his underwear and started sucking him. It was quite a turn on for me. I sat back enjoying the show. Pretty soon Eric grabbed Elaine's head and began face fucking her mouth. She obliged and kept sucking. Eric warned her he was going to cum if she did not stop. Elaine grabbed his ass cheeks and held on as he shot off in her mouth. She swallowed almost all of his cum. He pulled out of her mouth and collapsed on the bed. What a way to start our first MMF encounter. When he went to get a drink or use the bathroom I asked Elaine if she wanted to continue or had she just sucked him off to get him to leave. She smiled and said she had not been fucked yet and definitely wanted to keep going.

When he came back I was screwing Elaine missionary style. He watched for awhile as he laid on the bed. I finally got off her and moved behind her doggy style laying on our sides. Eric positioned himself so she could blow him some more. When he got hard again I got out of her and let him have her. She got on her knees and Eric started screwing her from behind. I moved in front and let her suck me. It was my dream come true watching Eric fuck her as she was blowing me. As you probably know f it is really a bit difficult to have a woman give a good blowjob and properly fuck at the same time so we mostly alternated fucking her.

Keeping in mind she was 29 or 30 and we all had a lot of sexual energy we kept busy sucking and fucking until all were satiated. He thanked us profusely and left. We collapsed in bed asleep. In the morning I was afraid she would feel guilty and say never again. I asked her what she thought about everything that happened. She asked me if I had a good time. I assured her I had and she said great. I asked would she do it again and she said probably but it would have to our special secret and we must be discreet
I did not take any photos, but later got her to wear the same garters and dress. We got to talking about how much fun we had. She started playing with herself for me and we ended up screwing on the floor. Hope you enjoy our little adventures.

[burllleee]

Great stories and great pics
Please keep posting, thanks

[John Skolte]

Elaine is a fine woman, Pantherfalcon.
From your story and judging by the very good pictures, I suspect she gave you many pleasant experiences over the years. Congratulations on your good fortune.

[Pantherfalcon7]

The term "cougar" was not really around in the early 80,s, but here is Elaine's first successful seduction of a younger man. I tried setting up a few more guys for Elaine. Some did not show, one couldn't perform and one was kind of a jerk and we sent him packing. I encouraged Elaine to try and find a guy she thought she might like. She was still hesitant. I think she was afraid I might think she was choosing him over me, but if I brought someone home it was okay. I told her to try and be aware of other guy"s paying attention to her and seize the moment. Not everything can be planned in advance.


> One night we went to a bar with a friend and his 22 year old . I was not even thinking about a threesome. There was a local band playing. My wife and the went to the bathroom and when they returned they were kind of giggling like young girls. During a band break the left and I didn't think anything about it. She came back and told my wife to come with her. Elaine returned 5 or 10 minutes later smiling. Ours friend and his soon left and I asked Elaine what was going on. She told me on the way to the bathroom she had told our friends she thought the drummer was cute. What she did not know was the knew some of the guys in the band and went and told the drummer about what my wife had said. He said he would like to meet her and to bring Elaine backstage during the break if she was serious. Elaine said she took him to a darkened area kissed him and told him she would fuck him, but it had to be a threesome with her husband. He seemed hesitant and did not say anything so she grabbed his hand and put it on her boob, massaged his cock and kissed him with passion. He said O.K. We only lived a couple of miles away. She gave him our address and told him to get his ass over there as soon as he could after the band was finished. We left about 15 minutes early and headed home hoping for the best.

> It was quite late so we decided if anything was going to happen we had to get with the program quickly. I suggested Elaine get into lingerie and meet him at the door. To my surprise she agreed. She put on a little blue teddy and white hose and no panties. We still weren't sure if he would show so I started kissing her and played with titties. I figured if he did not show I would finish the job and we would go to sleep happy, but disappointed he did not show up for the fun. We were about to give up on him showing. This was the early 80s and cell phones were rare. Suddenly we were interrupted by the ringing doorbell.

> Elaine met him at the door. He was pretty much speechless. Elaine kissed him on the cheek and invited him into the living room acting as if she was fully dressed. I walked in and she introduced me. I asked if he wanted a drink and went into the kitchen to get drinks for all of us.

> When I returned they were sitting on the couch making out like teenagers. She was in the middle so I sat on the other side and started playing with her ass. I left to go to the bathroom and give them some time to get things heated up a little. When I returned she had opened his pants and was playing with his cock. I sat down again next to her and she turned and kissed me then turned back and started sucking his cock. She was leaning over to suck him so I got on the floor and started eating her pussy. After a few minutes I could tell she was getting good and wet. She stood up in front of him facing away, bent over and backed up sticking her pussy in his face. He ate her until she was just about to cum. She asked for a condom, opened it and rolled it on him then stood up and eased onto his cock as he was sitting on the couch. She was grinding on him with her hands on his knees . I stood up and stuck my cock in her face and she was getting plugged at both ends.

> Soon she turned and faced him as she loves to have her titties sucked while sitting on a hard cock. We switched positions several times and wore her and the couch out. We had all been consuming alcohol and the rest of the night turned into a blur of fucking Elaine silly. Here is what she was wearing that night, The first pics is her standing at the front door, just like she did that night when he arrived

[burllleee]

Oh damn, he was a lucky guy
Very hot story,
Please keep posting, thanks

[Pantherfalcon7]

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 virginity

[Pantherfalcon7]

I mentioned earlier that Elaine was good at sensing if guys liked her. After setting up our first several experiences she finally picked up a guy at a grocery store, but that is another story for later. I encouraged her to be the one to decide when and with whom she wanted to screw. I figured if she was in the mood and liked the guy the sex would be better than if I was choosing when and where.


We were at a large gathering hosted by a local lumber yard. Free food, booze, live music and several hundred people in attendance. Most of the vendors were there promoting there products and everyone was walking around looking at the displays. All of the employees of the lumber yard were there and it was a very relaxed evening.

I was talking to some people when Elaine walked up to me, smiled and said it was time to go home. She said Todd wanted to come home with us. I was temporarily lost and thought she meant he needed a ride to his home. She grinned and said they had talked and he wanted to be with us and if dawned on me what she was talking about.
Todd was an employee of the lumber yard and we both knew him, but just casually. I trusted her instincts and said okay. Elaine said she would ride with Todd so he could find our house.

It was about a 15 minute drive and I knew Elaine would convince him, if he had any doubts. They had talked at the seminar, but in vague terms as it was a very public situation. She said he was a little nervous and wanted to know what to expect. He said he would love to have sex with her alone but had never been in a threeway before. She assured him I was straight and he would have a blast. When they pulled in the driveway she said she leaned over and stuck her tongue in his ear, placed his hand on her boob and massaged his crotch. He said he was ready and they headed into the house.

Elaine had learned how to perform and entertain both me and the other man. With the first few guys she was so shy she did not want me in the room when she first started playing them. I am definitely a voyeur and love watching Elaine and she knows it. She had gained confidence and was more relaxed than when she first started having sex with other guys. After getting us some drinks we sat down in the living room, the two of them on the couch and me in a chair close by. I told Todd to ignore me and just start having fun with Elaine. He was in his early 20s and Elaine was probably in her late 30s. After a little kissing and fondling Elaine stood up and took off her dress. She walked over to me, bent down and kissed me as I reached behind her and released her bra hook. As you know she has great tits and she knows it too. She stood back up a slowly pulled off her bra asking Todd if he approved. He smiled and reached for her. She teased him by covering up with her hands and showing me her boobs. I told her she should give our guest the first shot at her tits and she obliged by sitting on his lap facing him and sticking them in his mouth. He started sucking like a newborn baby. Elaine loves nipple stimulation and it always gets her going. Todd seemed content to play with her tits the rest of the evening.


Elaine knows I like watching her and gives me smiles, winks and sexy looks while playing with the other guy. I told her she needed to return the favor of having her nipples sucked and suck Todd's cock. She and Todd stood up and she unbuckled his pants and pulled down his underwear then pushed him back on the couch. She got on her knees and began licking his dick. She would stop and look at me and smile before going back down on him. Soon Todd said he was going to cum if she did not quit. She looked at me and laughingly asked what she should do. When we first started entertaining other guys I had told her a lot of men don't have ladies or wives who swallow and one of Elaine's best sexual skills is blow jobs to completion. I said the night was young and so was he. She turned back and told Todd to just enjoy. Elaine is great at licking and sucking while looking you in the eyes. She can deep throat a little bit and soon she sucked him dry. After swallowing as much of your cum as she can Elaine loves looking you in the eyes and smiling with a little cum still on her lips or chin. She wiped the last drops of semen from the end of his dick and licked it of her finger. He fell back on the couch and I clapped a couple of times and told Elaine she was great. She reminded us her pussy was still not touched. We headed for the bedroom.

Elaine has never been a big fan of anal sex. She has consented and let me screw in the ass, but it took begging. I finally figured out to start very slowly and let her control the speed of penetration. After several minutes of nearly no movement on my part she would eventually relax and I could bang her pretty hard in the doggy position. It always made me cum hard in her ass, but I was never sure if she really enjoyed it or was just pleasing me. I didn't push the ass fucking because she was so good in every other sexual pleasure. I had noticed the size of Todd's cock when she was sucking him. It was fairly long but not real wide. She had always told me I was too large for her butt. I didn't really believe her. I just thought it was an excuse to keep me out of her back door.

When we went to the bedroom Todd excused himself to go to the bathroom. As we were pulling back the bedsheets I said "Why don't you give Todd some ass action? He is long, but slender. Maybe you will like it." She just looked at me and said nothing. He walked in and we jumped in bed and began playing with Elaine's body like a sex toy. Todd stretched her legs apart and began licking her pussy with enthusiasm. She sucked me while he was eating her beautiful pussy. Pretty soon she grabbed the back of his head and orgasmed hard on his tongue and we all enjoyed watching her spasms of fun. Everyone relaxed and relished the moment. I went and refreshed our drinks. After several minutes of talking and taking it easy I reminded Elaine neither of us had actually fucked her. She said "Well what are you waiting for?"

Since I was the only one without an orgasm I got behind her doggy style while she sucked Todd back to hardness. After several minutes I could no longer hold back and shot off hard inside her. I rolled off her and just lay on the bed exhausted. Todd was uncertain of what to do as Elaine just lay on the bed not moving. I got up to go to the bathroom and told Todd he had better fuck her before she fell asleep. She just laughed and told Todd to put on a condom. When I came back they were fucking like it was their first time. He was not very tall and could fuck her missionary style and suck her titts at the same time. She rolled over and rode him for awhile leaning over and giving him her boobs. I reached behind her and, using the lubrication from my cum and her juices, slipped my finger in her anus. To my surprise, she did not object and continued fucking his cock and my finger. Taking a chance I asked Todd if he had ever fucked a lady in the ass. He mumbled no and I said to try Elaine's gorgeous behind. To my amazement Elaine got off of him and positioned herself on her hand and knees. He slipped his cock in her butt and I got the pleasure of watching my lovely wife get ass fucked by a 22 year old. She looked at me and asked if I liked watching her get fucked in the ass. I smiled and nodded yes and Todd said he didn't know about me, but he loved it. I said bang her ass hard and he did. I don't know if she actually climaxed but he came quite quickly and she seemed to be having fun.

We were all exhausted. Elaine eventually left to go to the bathroom. Todd started telling me how great everything had been and hoped I was not upset. I assured him I loved watching her enjoy herself and please us. He nervously asked if he could come back sometime. I smiled and said that was up to Elaine. She reentered the room and collapsed on the bed telling us she had loved screwing us, but was too tired to go another round. Todd was playing with her boobs when she was talking and seemed disappointed when she said the sex was over. He kept tweaking her tits hoping for another round. Elaine rolled over facing him and asked him if was sure he could get hard again because she was too tired and sore to last very long. Not wanting to be greedy he asked for a farewell blowjob. She smiled as she bent over and started sucking his dick. Either he had gone a long time without sex or really liked Elaine's mouth because it wan't long before he was climaxing for a third time.

When he got dressed he thanked us profusely and said he would be happy to come back again. Elaine smiled and said maybe. The pics are the dress and lingerie she wore that evening

[burllleee]

Love these stories
Please keep posting, thanks