Elaine's First Time

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Now that I am retired I have more time to tell a bit more about the circumstances surrounding the various photo shoots. I had recently moved into her house. She had purchased it with her half of the sale of her old house she and her ex had bought when they got married. It was a small bungalow built in the 40 s. Since I was in construction I started remodeling it for her and began in the bedroom by putting some wood paneling on one wall, new paint, new carpet and mirror on the door. After the carpeting had been installed I talked her into posing for me in a sexy sweater, suspender and hose. This was only the second session and she was still a bit shy. She finally took off the sweater and bared all in the last shot. Still one of my favorites. The beginning of hundreds of more photos and eventually videos. Hope I am not boring you with too much detailS-4.jpgS-5.jpgS-6.jpgS-7.jpg
 
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Awhile back I decided to rescan old prints I had. The newer scans were higher quality and a safety measure in case I ever lost them for some reason . It took quite a bit of time to scan them so I started putting multiple pics on each scan. My collection of photos were taken over nearly 30 years. They were an assortment of Polaroids, Instamatic and 35 mm. Regretfully I lost some of them. I found this old scan from probably 15 to 20 years ago. Sadly not the best quality, but I loved this outfit and set of pics. Would love to have the originals. A 2.jpg
 
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Elaine would put on one of her sexy basques for most of the times we were entertaining a friends. Most of the time we had sex it was just the two of us. She would always put on some type of sexy clothing. Usually a suspender belt and hose or teddy of something to add a bit of spice to the evening 910cc.jpg910dd.jpg
 
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I don't think I have ever told this story. He became our first FWB. He was the first man we had ever thought about having sex with that we had known as a friend for several years. He had even worked for me a couple of summers while in college. We had gone out on a couple of dinner dates and to the movies with him and his date. He did not have a long term relationship with any of these girls. One evening while I was talking to Elaine about trying to find someone to fuck she said "What about Mike?" I was surprised because she had always wanted to do people she did not know or were not considered good friends. I said "Are you sure?" She said he was everything she liked in a man, tall, good looking, had recently broke up with his GF and we were already good friends. I agreed but just wanted to make sure she was okay with it. He was 25 and we were about 40. We had never tried to seduce someone we knew this well and were a bit uncertain of what approach to use. Many men actually get nervous and hesitant about 3 way sex so we finally decided to just surprise him and hope for the best.

We invited him to our house for dinner and drinks. I cooked steaks outside on the grill and we enjoyed the food and wine. After dinner and some small talk I said we had a surprise present for him. I told Elaine to go get it for him. We had obviously discussed this and set it up in advance. She had her lingerie already set out along with her lipstick for a quick freshen up. While she was upstairs changing he looked at me kind of funny and said "What's the deal?" I said we had done this before and always liked it and thought we should share our fun with him. He just looked at me like what the hell are you talking about. I smiled and said you will know in a minute or two. We were in our living room and I had sat in the chair next to the couch making sure he sat there. I set our drinks on the coffee table. When I heard Elaine walking down the stairs I told him to close his eyes for a few seconds. When he opened them Elaine was standing in front of him dressed in this outfit. He was speechless. These pics are not from that evening but are the outfit she was wearingoffice1.jpgoffice2a.jpgoffice3a.jpgoffice4.jpg
 
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To say he was flabbergasted would be an understatement. He kept switching his eyes from me to Elaine. I smiled and said "Go ahead and get started. I will just watch for a bit before joining." He said "You mean we are going to Tag Team her?" I smiled as Elaine moved to the couch and sat on his lap. She wrapped her arms around his neck and said "Mike, I am going to show you how a real woman fucks and make you forget those young girls." She kissed him and said "Well, are you ready?" I think he was still in shock as Elaine got off his lap and told him to stand up. She unbuckled his pants and pulled them down with his undies and bent down to suck his cock. Soon she had him hard. She stood up and said "Let's go to the bedroom. You two are too big to fuck on this couch". office5.jpg
 

Warbird

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May 6, 2018
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I love the expressions in the first pics. Bet the dude was surprised and then enjoyed himself later ummmmm
 
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I loved that we were all so comfortable with each other. She just took charge from the start when she took us to the bedroom so we could have more room to fuck her. When he worked for our construction company we had a rule with the employees that if they broke something they had to pay for it. It was more of a threat than actual policy. Just a way to keep them on their toes. I am saying all that to explain this. I have said before that Elaine will let a man cum where he wants. Sometimes she just tells them and sometimes they ask Mike had been fucking her for quite awhile in several positions and said he was about to cum. She said just go for it. Most guys tell her or ask if they can cum some specific place. He was doing her missionary style with her ass on a pillow and holding her legs up when he suddenly pulls out, grabs his cock and pumps several large blasts all over her. It went over the front of her basque, tits, neck, face and hair. We were both kind of shocked and when she recovered and asked for a towel. As she wiped off her face she looked at him laughingly and said, "You are going to have to pay to have my outfit Drycleaned". Just the first of many fun times. She was squeezing her arms together on this pic trying to make her tits look bigger. Had me shoot the photo aiming up to even make them appear larger than they are. Awhile back I posted that same basque. Not sure if it would still fit but pleasant memoriesoffice6.jpg
 
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Later when we were just talking she asked him about the big pull out and blasting her with cum. He started to apologize and she interrupted and said she actually enjoyed it as it reminded her of her favorite porn actor Peter North and how he cums in a lot of his movies. Mike said he watched porn with men cumming on women a lot but none of his GF s wanted him to do it. He also said none of them had ever worn a basque and hose and the entire scene made him think of porn movies so he pulled and let it fly. He said his cock wasn't as big as Peter Norths but he would cum wherever she wanted him to. She said "Let's start round two"unnamed (23).jpg
 
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I agree, but we were quite away from taking photos of her having sex with someone else back in the 80 s. I was just happy we were having sex with other guys.
 
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orgasmsrus

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Jul 19, 2018
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I agree, but we were quite away from taking photos of her having sex with someone else back in the 80 s. I was just happy we were having sex with other guys.
What was the game changer for you that meant you fully embraced the hot wife lifestyle?
 
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I am not sure I can explain my sexual desires and where they came from but will try. The most difficult thing for most people on these type sites to understand is that I I was probably in my 40 s before I ever even heard of the Cuckold /Hotwife lifestyle.

I know I fell in love with lingerie, especially suspenders & hose in HS because my first GF I had sex with wore them and I loved the feel and look probably because I knew it was going to lead to sex. We split up after a year and a half because we were starting college and she thought we should date around and get back together after college and get married. What actually happened was I had sex with her for the next 15 years, LOL. I was a college athlete and in the late 60 s and early 70 s there was a lot of "Free Sex".

I married my first wife right after graduation. We had been dating our last two years in school and attended some wild parties and experimented with lots of different things. After marrying we did some wife swapping and swinging. The sex was good but often some drama came with it and took away the fun. We divorced after 10 years.

I dated several women but none seemed interested in any thing except monogamy. I was a bull for several couples before I even had heard the term "Bull" To me I was just partying with some friends. Eventually a friend introduced me to Elaine. They worked together and he suggested I take her ask her out. We hit it off and I really started to fall for her but knew I could not lead a normal married life.

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. After our first MMF experience I was worried she might feel guilty the nest morning 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.

We tried a few sex parties. They were monthly gatherings of local swingers, held a local hotel or large private residences. I felt comfortable, but Elaine was never really at ease. She experimented with women and said it was ok, but preferred men. We decided after a few parties we liked more one on two or one on three type situations. I got to watch her having guys lick her while I was getting a blowjob and be with other couples and keep switching partners. While she was so willing to do whatever I asked I thought if she felt uncomfortable at those places why go. I think her desire for younger men at the beginning was because she was unsure of her own attractiveness and did not think other men would find her desirable, while younger men might be more willing. I encouraged her to be on the lookout for guys hitting on her as they would probably be more open to threeway sex.

Orgasmsrus, I know I may not have fully answered your question but I guess I knew she had fully embraced the lifestyle when she successfully convinced men to have sex with us without me have to set it up. She became better at being able to tell which guys were interested in her and knew how to seduce them into joining us in bed. Lots of guys want to fuck her but only by themselves. She became very good at letting them sample the goods just enough to make sure they were willing to show.

Please feel free to ask any questions you may have about us and our lifestyle. Guess I should not post this much text without some kind of photo. How about getting ready for a datepost-5233-0-59006500-1440943759.jpg
 
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You can post as much text without photos as you want. Your life together with Elaine is absolutely fascinating to read about. It's extremely rare to get as much detailed information from a couple's past as you've provided everyone with. I'm sure everyone, including myself, appreciates the amount of time and effort you've put into keeping us informed with text and photos.
 
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I think I have written about most of our memorable experiences with others. Sometimes comments and questions from people trigger memories for me. Feel free to ask any questions you may have about us, individually or as a couple. After every thing I have posted about our private lives I don't think you can offend me with anything you may ask. On our first few trysts I was just happy if it happened at all. When I tried to get her to wear extra sexy clothing, lingerie or makeup she was still too nervous or insecure about her own desirability to do it. I did not push the issue because I didn't want her to cancel the evening. Looking back I think she may have thought I was insinuating she wasn't sexy enough to be attractive to other men. As she gained more experience and confidence in her own sexuality she slowly gained the confidence to dress more provocatively including lingerie and make up. On this evening we had invited our first FWB over for a second time with us. He was our first man we offered a second time to. Since we all knew what was going to happen I asked her to really make herself look extra hot and for the first time she obliged. Extra makeup including false eyelashes which she seldom wore, french bra and sexy sweater, suspenders and hose. We had a large swimming pool and the chlorine was starting to give her black hair a deep red tint she did not like and she had it lightened. You can see the different look in these photos. We had a great meal at our house with her sexy look left no doubt about what was for desert.rs.jpgrs2.jpgrs3.jpgrs4.jpgrs5.jpgrs6.jpg