Diary of First Time

And each day I made it clear that I wanted him to do a bit more for me around the house. First it was asking him to carry the laundry upstairs while I was busy.

Then it was asking him to just put it away while he was up there. Then it was to do the dishes while I tended to something else. Always would I ask him to do these things just before he was going to ask to jerk off. Therefore, as I was building up more passion in him, he was only being rewarded with making my life easier around the house. This was a lesson that I should have learned a lot earlier. My how husbands are motivated by sex to be much more helpful around the house.

After a week had gone by I asked Jim to read one of his emails to me while I masturbated. He was embarrassed by the thought of this and at first said no. But I gently caressed his cock and told him how much it would turn me on and he agreed. As he read the email from my cell phone I kneeled between his thighs and gave him head for the first time in years. His voice trembled as he read, trying to focus on the words as I licked and sucked his 7 inch cock. As he got close to climaxing I pulled my head away and pumped him to orgasm where he exploded. Very quickly, while he was still climaxing I rubbed some of the cum along his lips and kissed him deeply. He was in heaven.

The next morning I reminded him that I was going out of town for business later in the week. There was a conference over on the coast and work was sending me for three days and two nights. I told him how much I enjoyed him reading his email to me last night and how it would be so sexy if he could do that for my iPod and have it with me while I travel. At first he was nervous about doing it. He protested "What happens if the kids find it?" I assured him that I would keep it locked up on my device and change the password so that the kids couldn't access it. I added that I would make it worth his while tonight and lo and behold all seven emails that he sent me were recorded as MP3's by later than night.

Chapter 5:

That night I didn't allow him to jerk off. We were getting into a rhythm that he could predict and I wanted him to be reminded of my new position in this old relationship. I asked him if he would rather have the real thing rather than wanking off his little peter all by himself. Although we had been having fun each and every night I had been holding out the grand prized strategically.

I brought him up to bed and laid him down. I wore a nightie, which I hardly every do, and I seduced him. I placed the iPod next to the bed with him verbally describing his fantasies to both of us and it drove us both mad with desire. He manhandled me like he hadn't since our honeymoon. My small breast came alive again in between his lips. My ass felt firm again in the grip of his firm hand. His cock entered me swiftly and confidently. My nails dug into his back and I spread my legs like I was a teenage cheerleader again. The only disappointing part of it was how quickly he came.

And that was part of my plan. I immediately seized on the opportunity saying "No.... no.... no.... no... honey, come on baby.... hold out longer Jim....no.... don't cum yet baby.... I need you more baby...." pouting a bit and showing my loving disapproval. He went from euphoria to almost being in tears.

He started to say "But Neen, its been so long", but I immediately shushed him.

"I need more" I said and guided his head down between my legs "finish me off. I need to cum"

And he went to town as if this was the first time he had ever eaten pussy. To tell you the truth he was never very good at it, but at that point I didn't know what a good pussy cleaning was. I intentionally held out and made him work to get me to cum.

When we were done and snuggling together I let him know what an animal he was leading up to the sex. That was going to keep my eye from straying too much while I was away at the conference. But then I was sure to remind him that "I only wish that you could have lasted longer baby."

The next night was the night before I left for the conference and Jim found the courage to ask me "Are you really going to look at other guys while at the conference?"

I responded devilishly, "Look? Definitely. Do something more? Perhaps?..... Isn't that what you were fantasizing about?"

Now deep down I knew that I would never do anything at the conference. I was scared shitless of where this was all going. I had never been with anyone other than Jim and it took me forever to let him get by my defenses. I knew that Jim was safe, but Jim's head had been spinning from the past week and a half. He didn't know that in my new found confidence I wouldn't push any limits.

Jim responded with "Neen. Come on now, hasn't this gone too far already?"

To which I shut him down with "Oh Jimmy, you know you hate it but you love it at the same time? I think you are safe for the time being anyways. My period is coming on. Won't you be a good boy and run down to the store for some pads and tampons for my trip?" When he returned I was already in bed and left him a note that he should have hurried home sooner. Now there was no time to jerk off for me. I had to get up early for the flight and didn't want to be bothered.

Chapter 6: The Trip

The next morning I left for my trip and it was a legitimate conference. I sat through workshops and manned our booth in the exhibit hall, but I couldn't stop thinking about the situation that I left Jim in. He was really second guessing everything that I did.

Typically when I went away I was pretty straight and narrow. After a business dinner I might have one drink in the hotel bar, and then went upstairs to skype with Jim and the kids. This time however I made sure to call during dinner at home, get passed around the table to check in with the family, and then told Jim that I would call him later. I was going out with "some clients".

There really were no clients, but Jim didn't know that. And poor Jim couldn't jerk off without permission. Now what would he do? And he knew that I would check the computer and phone history when I got home to see if he tinkered. I sat in the hotel bar making small talk and two different fellows bought me a drink. I wasn't in to either of them, but it sure did feel nice to flirt. I was almost 40 and still had "it".

I called home at about 11 pm to see how Jim was doing and he picked up on the first ring. He was waiting for my call. He wanted to know if I was OK, where I was, who I was with, a play by play of the night.

I was coy with him, but reassured him that nothing had happened... and I added at the very end "yet". I told him to switch over to skype so that we could video conference. While he hung up to call back I set Skype to record the conversation.

When he rang me back I picked up via the webcam and saw how pathetic he looked. He was hanging on my every word like he did in college. He was nervous, but excited by this game. I got him to tell me how frustrated he was that he needed permission to jerk off. I asked him if he wanted permission to do so now. He nodded yes.

I told him that he could jerk off for me on Skype if I could watch and he told me about his fantasies. He was shy at first, but he wanted release so he was going to do anything that I asked of him. He took off his shorts on the camera and spanked his cock while telling me that it drove him crazy to wonder if I was with another man. I allowed him to cum and asked to see him lick his fingers for me. When he did, I adjusted the camera and turned off the record feature, then masturbated for him as well.

The next day was another conference day, but I was done at about 4 pm. There was a spa at the hotel and I decided to get a massage. I requested a male masseur, but this wasn't one of those sketchy strip mall massage parlors, this was a real day spa at the hotel and the massuese was named Hans, what else?

I texted Jim to call me during my massage so that he could hear Hans in the background and my little sighs of delight. Out loud during the phone call I assured him that Hans wasn't doing anything frisky with me... yet. I did enjoy laying on the table naked and draped only with a towel. Hans was a perfect gentleman with strong firm hands, but Jim didn't need to know exactly how professional he was being.

And then came the humiliation. While I was in the massage, with Hans listening to my conversation, I asked Jim if he wanted permission to jerk off for me. Jim was so embarrassed. He was almost pissed at me, but more pissed at himself for finding himself in this position. I assured him that it was ok. Hans didn't mind if he was jerking off to porn on the other side of the line. I even checked and bluntly asked Hans specifically. He laughed and nodded that it didn't bother him at all. I think Hans liked the mental torture that I was putting Jim through.

I almost thought that Jim wouldn't do it. This might be the end of the line. But then came the question seeking reassurance. "Do you really want me to jerk off, Neen?".

"Yes honey" I replied. "Pull your dick for me".

The thought that another man was listening in on me talking dirty to my husband drove us both to new levels of passion. Jim came very quickly and I started to get very squirmy in my massage, and I am sure that my cunt started to glisten as I lay there on the table.

Jim hung up quickly and I asked Hans to stop. Even though I was very turned on, I was also horribly scared. I had let my libido get the best of me and all of a sudden I felt horrible. What would have happened if Hans wasn't so nice and understanding? How would I have defended myself? While this was all so erotic and exciting, I was scared and went back to my room. I actually had to pour a bath to relax. I poured myself a glass of wine from the minifridge in my room and once I was OK again in my own head I started to finger myself. It was a strange mix of exhiliration, danger, eros, and passion - all because of the sitatuion that I was creating.

I was rather pleased with myself.

Chapter 7: Second Thoughts

When I returned home from the trip Jim was almost beside himself. He was really embarrassed by me humiliating him in front of the masseuse. I explained to Jim that that masseuse was some one neither of us knew, nor would we would ever see again. Christ, masseuse never even saw Jim and wouldn't be able to recognize him if they were in the same room again.

That being said, Jim still protested and questioned whether he wanted to do this anymore. I had been prepared for this. I knew that it might come to this at some point, so while Jim was throwing his hissy fit about this going too far, I simply watched and waited for him to be finished. When he was done I simply pulled out my phone and played back the emails that he recorded for me with all of his fantasies.

I looked at Jim and asked very calmly "Jim, how do you think that the partners at the firm would react when they heard these audio files?" And after a moment, I added "or read your emails?"

Jim started to stutter and was obviously taken a back by the threat.

And finally I added..."On and then there is that little Skype video that I recorded, isn't there? While I was away I made copies of all of these and put them in safe keeping. Oh no honey... you put me through hell while you were having fun with your fucking affair. Its time for me to have my fun, damn it!"

The odd thing is that deep down I don't really know if I would have shared those files with anyone. If push came to shove and he really challenged me I would have caved, but he didn't know that. Having the power was really going to my head and I kind of liked it. It was as if I was living my alter ego. After years of being safe, I was now spreading my wing a bit and I was loving the freedom.

Jim's shoulders slouched forward. His eyes went down to the floor. He knew he was guilty. He thought that he had been paying his penance these past few years with little to no sex. Now he knew that his cock was coming home to roost. He nodded. He was defeated. I had the upper hand and he willingly gave it over to me.

"We will have no more of that will we Jimmy?" He noticed the change in my tone and my choice of names for him. He shook his head no, but I demanded a verbal answer "I can't hear you."

"No Nina"

"Good. I will let you make it up to me by setting up our first meeting."

Chapter 8: Arranging the first encounter

I put Jim in charge of finding my first partner. Why? Well first of all, I had no idea how to set this up but I knew that he was far more into this fantasy that I had ever been until now and therefore was pretty sure he would be able to figure it out even if he didn't know right then. Second, how humiliating for him. He was going to arrange for everything and be part of the process. And third and probably most importantly, I am still a scaredy cat and wanted Jim to be part of all this so that I was safe. Remember, I had never slept with anyone but Jim since my father raped me as a teenager.

Jim was hesitant at first and asked if I was serious. I assured him that I was (even though I really wasn't). And so he started asking me questions. Did I want to go through Craigslist? Did I want to post a profile on a dating site? Or more specifically a fetish/cuckold site? Did we want to meet someone randomly in a bar? Did we want to go to a swingers or fetish club? Did we want to hire an escort or masseuse and pay for the first time?

Holy shit! I had no idea that all of this stuff existed. How sheltered I must have been to have lived three decades on this earth and have no idea that there are sex clubs a few miles from my house. And why did my husband know about all of them? He assured me that it was because he had read erotic stories online. I didn't push the issue and went with it.

Craigslist seemed kind of sketchy to me and I had heard about all sorts of serial killers and shit. A regular dating site seemed out of question, how do you go from looking for a date to "Oh, I'm married and my husband wants to watch"? I was in disbelief that there sex clubs out there where people just met up and fucked in public; and although it intrigued me I needed baby steps. And to hire someone to fuck me? Although it seemed easier and more clear cut, I wanted there to be true passion there, not where is my $100 and see you later.

Therefore it was an adult and cuckold dating site. Jim found one and we browsed through some profiles to get an idea about what people write. We agreed that we wouldn't put any pictures of our face up, but that pictures of our bodies would be fine. Jim wrote the profile and I edited about 20 times. I kept being more conservative and revealing less, while Jim was prodding me to make it more enticing and honest. We found a happy medium. The profile read:

"Late 30's Caucasian couple seeks friend with benefits for wife. New to all this and need someone who is patient and willing to work with us. This won't be sex on the first date necessarily and husband will be present for the entire time. No male-male contact is necessary, but could be considered (that made Jim cringe, but also very excited). Wife is petite, 5'3", 125 lbs, 34B, fairly innocent and up for adventure. Hubby is submissive, 5'9", 190 lbs, and clean cut. No drugs. No diseases. Respectful gentlemen only need apply. Safety is a priority and we will only play with condoms at all times for everything."

We took some pictures and were both so excited we stopped right there and made love. Wild crazy love. Exciting, passionate love like when it was all new. Jim was trying to please me. The idea of me being with another man made him put his heart into it more. He was competing for me now and you could sense that he didn't want to lose me now. He wanted to show me something and wow, did it make a difference. The thought of sleeping with other men was exciting for me, but also scary. The effect it had on my husband was incredible! Who knew if I actually had to go through with it, but the immediate effects of talking about it certainly started to change things for Jim and I. We were having fun again. After we both came and came hard we gathered ourselves together and returned to the computer.

Jim posted the profile and to my surprise we received 8 responses the first day. In my head I didn't really know if I would turn heads. Most of the responses were pretty shameless and dirty, but one stood out above the others. It was a younger black man, 27 years old from the other side of town. He was a professional and said that he loved taking care of MILF such as me. He had been a bull for a few couples now and would be patient and kind like I asked for in the profile. He may have been the only one that actually read the profile and didn't just look at the pictures. His name was Tyree and I told Jim that I wanted to meet him and to set it up.

Chapter 9: The First Encounter

We replied to Tyree's email and said that we wanted to talk to him further. We exchanged a few more emails where he said all the right things. He flirted with me and complimented me and told me what he wanted to do to me. This made me feel on cloud nine. There was a younger, handsome man who was interested in me. I felt like a school girl again when you knew that there was a boy interested in you for the first time. In my emails back, I kept cautioning him that I was a slow mover and was still feeling all this out. That it was my first experience doing this and that really seemed to make Tyree even more interested. We made arrangements to meet up next Saturday night at the Casino dance club.

We arranged for my mother to come over and babysit the kids for the night. We told her that we were going out to the casino for a night of fun and didn't want to have to drive home after a few drinks so we were getting a room.

We were supposed to meet Tyree at 10:30 pm in the dance club located at the casino. We arrived at about 7 pm and got a room and then went to dinner. All through dinner I was so nervous and talked to Jim about it. Under the table I kept caressing Jim's cock with my toes and he was very excited. I made Jim promise to protect me and he suggested that we come up with a safe word. That way in case I was really scared he could tell the difference between a playful "no" and a meaningful "no". We agreed on "Jay". If I called him "Jay" instead of "Jim" that meant that it was game over and Jim would interrupt to end things.

We barely made it through dinner without Jim's hands all over me and we ran up to our room and fucked like crazy. I kept taunting Jim that I needed to save myself of Tyree but that just made him more passionate and more excited. We had the best sex of my life that night. I was almost tempted to call it off and simply be happy with the spurring my husband to jealousy. I was loving the effect it was having on him. But thankfully I didn't cave.

When we were done, I hopped in the shower and asked Jim to wait on me while I got ready. This killed Jim inside. He hated it and loved it all at the same time. He had just given me the fucking of my life, and now he had to lay out my dress and panties for a date with another man. He was looking for a trophy and I handed him a broom. But he did it. Almost to my surprise. He sat there on the bed and helped me get dressed. He handed me things for my hair and make up. He listened to me debate which dress and which stockings to wear. On some levels I think that he was more into it than I was.

It was 10 o'clock when we headed down to the dance club. It was still filling up and wasn't exactly packed yet. We told Tyree that I would be in a red low cut dress at the bar and that Jim would be black pants and a grey shirt. He hadn't seen our faces yet, but we had seen his.