Elaine's First Time

Robert Smith said:
The following is a collection of some emails I exchanged with guys wanting to know more about the lifestyle. They are not in any particular order, just answers to questions they had asked.

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.

I think you may be more of a cuck and me more of a wife sharer, but it is a fine point. Two sides of the same coin. We both get excited watching our wife's suck and fuck other men. I have never been the jealous type. Did a lot of running around before getting married. I knew I could only marry a woman who enjoyed the lifestyle I liked. Probably why I talked her into it in a year. Over the years we became more aggressive on my urging. I wanted her to be ass fucked, dp'd, gangbanged, fuck big cocks, fuck black guys, try a women, go to sex parties,etc. She did nearly everyone of them at least once. People like you and me understand the thrill of watching it happen, but most people think we are weird and have no concept of being cuckolded or wife sharing.

To my knowledge she never fucked anyone else without me being in the room or at least the house. Yes she did fuck more than one guy and me at the same time, again with my encouragement. If we liked a man, in and out of bed we might do him more than once. I would say most were one time sex romps. Did friends, but no relatives

Elaine married her high school sweetheart when she was 18 and had dated him since 15. She said they only had oral sex. Today that seems tame, but in the late 60s the sexual revolution was just beginning. After graduating from college she became a grade school teacher and she and hubby bought a small house. He had a job as a salesman for a brick company and they thought all was blissful Soon divorced, but remained friends. I had gone to university and did a lot of wild partying with lots of girls. I married after graduating and divorced 9 years later. When I started having feelings for Elaine I told myself I was not going to marry until I was sure we were sexually compatible. Elaine had had two relationships before we hooked up, but had led a relatively straight sex life. She was great in bed, but had never done two men before. She said she never even thought of it. I was the one pushing the issue and it took over a year to make it happen. Once she realized I was not going to be jealous she opened up and became more willing to do most of the things I asked. As I look back at the past 35 years I was the one always pushing the limits and she slowly loosened up and let me lead the way. Ask anything, no matter how personal. Early on she was using an IUD and as AIDS did not exist she let guys go bareback in the beginning. We started using condoms as we became more daring with the men we choose. She would usually let a man climax where ever he wanted. Had a great ability to swallow while keeping your cock in her mouth after you shot off. Like you I encouraged her to go braless and wear revealing clothes. One of my fetishes is lingerie, suspenders and hose.

Probably the only thing she did not do for me was to actually get gangbanged. She did several men in an evening of partying, but it was at her choosing. Sucking some, wanking some. letting her boobs get fondled, etc. But she never let multiple men line up and fuck her like some whore, one right after the other. Can not complain though. She was pretty much up for whatever I suggested or she thought she might want to try. Never were into bondage, pain, ******** or humiliation. I was never into homosexual stuff, but told many of the men I coached into the lifestyle that you can not be afraid of touching another man or letting him touch you. Impossible for two men to fuck and suck one woman at the same time and not have contact with each other. I'll see if I can find stories about that. Still waiting to hear about your secret fantasy or fantasies you never got to indulge in.

Elaine like an average to large sized cock. Does not mind slightly smaller as long as the man can keep it good and hard. Insists on a man going down on her if he wants the same in return. Has fucked some very large dicks and if they stated slowly she could take most of their big cocks. She really likes more normal size guys as they can fuck with abandon in many positions and she does not have to worry about getting hurt by giant cocks. You can see the almost nervous look on her face with this guy. It was a sex party a friend hosted and this bull was the featured entertainer. The women got to see him in action and volunteered to fuck him if they felt they could handle his size. It is one of a few photos she lets me show her face. Think she was actually kind of proud she had the nerve to let him fuck her for a bitView attachment 90749
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That's a great pic and a really nice cock stretching Elaine's pussy.
 
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Robert Smith said:
I always like hearing what other men find attractive. Too bad I am not a porn movie director but when we are in the middle wild sex I never yell "Stop so we can get a closeup of Elaine's clit" It is also hard to take a pic when the lady is playing with the dildo or using her fingers and hand as it blocks a lot of the view. Here are a couple but clit is not totally arousedView attachment 438982View attachment 438984View attachment 438985
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Based on your photos and videos you're an excellent photographer and cameraman.
 
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Robert Smith said:
I know a lot of men like cloe us gyno pics but they have never really appealed to me. I like the partial nude and lots of lingerie. If you go to around page 50 of this thread you will eventually see about every photo I ever took of Elaine
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I agreed with 100%. Your partial nude and lingerie photos of Elaine are the best.
 
Robert Smith said:
Part One

The problem with having a great, sexy and willing wife like Elaine is that I was never satisfied. Don't get me wrong, I really enjoyed what we were doing, but I always wanted to expand the horizons. Elaine really liked the sex but had to be pushed a little to get her to the next step. The next thing I wanted was to see Elaine do two other guys and me. We had gone to a couple of swinger type parties and group settings, but she wasn't real comfortable with them. Our friend Todd continued to stop by hoping for another shot at Elaine. She liked Todd and we had been together a couple of times since our first encounter.

One summer afternoon Todd came by the house with a friend. We were at the pool in the backyard. They brought some beer and we all enjoyed the sun and suds. The guys had to leave and as they were walking away Todd asked me if he could come back later in the evening. I told him to bring his friend and maybe we could all fuck Elaine. I said it could also backfire and none of us would get any pussy. I told him she had never done 3 guys and had turned down my requests in the past. He said he wouldn't push the issue but sure hoped she went along and let the three of us screw the hell out of her. I said we would just have to play it by ear.

After they left we cleaned up and fixed something to eat. Elaine wanted to know if Todd was coming over and I said I wasn't sure, but he was going to try. While enjoying a glass of wine the bell rang and Elaine went to open it expecting Todd. She seemed a little disappointed when his friend was standing next to Todd, but she cordially invited them inside. She was wearing a polka dot crop top and shorts. They both complimented her attire and she just laughed. She had no bra or panties and the tops was tight with her nipples obvious to all. After some idle chit chat I think Elaine expected them to leave. I decided it was now or never and asked Elaine if she would finally fulfill my fantasy. She just looked at me trying to figure out exactly what I meant. I pleaded "We all want to have sex with you tonight" She said "Are you crazy?". We all nervously laughed. Todd smiled, walked over to where Elaine was sitting, put his arm around her and said very sweetly "I have been telling Mike what a great piece of ass you are and he needs to experience you just once" That broke the ice and Elaine seemed to actually be considering doing all of us.
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Love those glasses.
 

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