Evolving Sex Life Pt. 02B

On Monday and Tuesday, I was too embarrassed to ask to masturbate. On Tuesday night after dinner we were sitting on the couch watching TV and she put her feet in my lap and asked for a massage. As I started massaging her feet, she asked me how many times I had masturbated, and I answered that I had not done any. She said, "Well you better get busy. You have to get fifty per week to get to one hundred. In fact, you better ask me right now so you can masturbate while you rub my feet."

I looked down and asked, "May I masturbate while I massage your feet."

"Yes."

As I unzip my pants, she said, "No. Get down on the floor."

I crawled down onto the floor and pulled my penis out and started masturbating with one hand and massaging with the other. After several minutes Julia seemed impatient. "Why haven't you gotten to the edge yet? Is this not exciting enough? Use both your hands."

As I started masturbating with one hand stroking and the other massaging my balls, she put her foot to my mouth and said, "Suck on my big toe."

I put her toe in my mouth and very quickly I reached the edge and begged to come. Of course, she said no. After about an hour, many edges later and sucking toes on both feet, Julia pulled her foot away and said, "You better ask me each morning if you can masturbate and edge. Now let's go to bed."

On Wednesday we woke up and I asked to edge. She said, "Yes, and you will get at least ten edges."

I sat down in my home office and googled "humiliation". Most of what came up was cuckolding. The second most common was small penis humiliation. These were a little interesting but not really. One of the videos was of a mistress with very long nails. She was humiliating her slave's small penis as she abused it. When she started inserting her nails into the tip of the penis, I reached the first edge. For the rest of the day I wasted an inordinate amount of time masturbating and edging to her long nails masturbating or being inserted into different slaves' cocks. By the time I had finished that day, I had edged twenty-four times and wasted a lot of work time.

On Thursday, when I asked to edge again, Julia asked if I had achieved ten the day before. I answered yes but did not tell how many. She seemed satisfied and told me to get at least fifteen when she gave me permission to edge that day. I knew fifteen would be easy. My plan was to find porn about long nails edging, denying, and torturing cocks. It had not been a week since my last orgasm and my arousal grew with every passing day.

Mistress Nikita, Mistress Persephone: With those two alone I was able to quickly achieve fifteen edges. The morning took over and I was barely able to focus on my video conference (VC) meetings. After lunch I stumbled across Nikki Ashton and her long fingernails and toenails. This was new and erotic.

On Friday morning, when Julia woke up and I asked to be allowed to edge, she told me that I could edge but only to fantasies of her. She said, "I know you look at porn and masturbate and I assume you masturbate thinking of other women. Not today. Today you will only masturbate to fantasies about me."

Masturbating to pornographic movies or pictures is easy. I pulled up some old pictures that I find very erotic. I have lots of gorgeous pictures of my wife and the first ten edges of the day were spent looking through old pictures and remembering some very erotic things we had done in our early years. There was the weekend of the full body cast. Corsets at Folsom fair. The vacation weekend in long arm casts where I was totally helpless. Bondage tied over a railing on a hotel balcony. Remembering these events was a wonderful walk down memory lane as well as a way to self-pleasure.

In the afternoon, an idea popped into my head. I opened up an online picture-editing software and I loaded a picture of my wife. After about thirty minutes of manipulating the picture, I had a reasonable image of my wife with her natural three-inch-long nails from earlier in our life, and now, one-inch long toenails. The fantasy of kneeling below her and being humiliated by sucking on her long toenails was new, exciting, and oh so erotic. The rest of the afternoon was a flurry of edges in between meetings.

On Saturday, as I woke up, I was not sure what to expect. When Julia woke, she rolled over and kissed me and said this is going to be fun. "Just like your birthday. You are going to service me with no reciprocation." One of her birthday presents each year is an oral orgasm for her. Simple and clean. She told me to lick her and I crawled between her legs.

Following her instructions, I licked as she directed and inserted one finger up and one down to stimulate her inside. The first orgasm was a long time in coming. She took it slow and slowed me down when she was getting too aroused. It must have been over thirty minutes when she shuddered and yelled through the first orgasm. Julia is very loud, and luckily, we live away from close neighbors.

When she was finally satiated it was over an hour and my jaw was tired and sore. She looked down at me between her legs. "Don't you wish your cock could make me come like that?"

"Yes, Mistress, "I mumbled, turning red."

"Would you like to make love to me right now? Put your worthless cock inside me? Would you like me to let you come inside me?"

"Yes, please."

"Well, that's not going to happen today. Today you are not even going to touch your cock. You are going to get up and get to work in the yard. I have a lot I want done today and you are not going to waste any time masturbating." With that she got up and went to the shower.

I wasn't sure exactly what to do. I was extremely turned on and the front of my underwear was soaked with precum. After a few seconds, I followed her into the bathroom and showered. The honey-do list was long, and we spent the day in the yard working. I did not masturbate but I wanted to all day long. After seven days and over fifty edges, combined with the long session of oral for her, I was dying to come.

Monday was a busy day with meetings. I woke up before Julia and was on my first conference twenty minutes later. By the time I realized it, Monday was gone. Tuesday, when I got my first break it was a two-hour period in between meetings. I needed to finish a report and presentation, but my mind had been drifting back to sex.

I texted Julia and asked if I could edge. She asked me how many times I had edged since Sunday morning and I honestly replied none. She was surprised and her next question took me a little by surprise.

"What porn are you going to edge to?" I hadn't really thought about it yet and I told her so. Her next text asked me what arouses me most.

That's easy. "Extremely long nails," I wrote.

"And what is the most humiliating thing you want to try that you have not tried? Be honest!"

I thought about it. There are lots of things that are humiliating that I want to try and lots that I am committed not to try because I think the risk is too great either physically or emotionally. I thought for a second, trying to decide what I wanted to tell her. There were many that I was not willing to admit to wanting to try. I wasn't sure how she would react to some of the more extreme. I settled on strap-ons. Being pegged could be very humiliating and I did want to try it. We had done some anal play before, so this was a safe answer.

"OK then, google long nails and strap-ons and have fun," she texted back.

I was relieved she had not made me admit more humiliating things. She had already seen most on the BDSM checklist we had reviewed a few weeks earlier. I googled +"long nails" + "strap-on" and I found my way to a mistress whose website was called Obey Nikita, and it was easy after that.

I quickly started edging and before I knew it, I was almost late to my next VC. I was still erect and dripping as I logged in. Luckily, no one could see below my chest on my webcam. I hoped my face wasn't too flushed from almost two hours of edging.

I was surprised on Saturday when Julia texted me. I was up early. She was sleeping in. She asked me to come back to the bedroom. She told me she was horny, and I needed to worship her pussy. It had not been two weeks so I was surprised and thought I might get to come. She told me to get undressed and put a towel down and to hump the towel while I licked her. A few minutes in and she asked me if I was enjoying humping the towel. I was not going to make the same mistake twice. "Yes," I said. As she got more and more vocal, I was getting more aroused to the rough material of the towel that was now soaked with my precum.

Between moans she said, "I cannot believe you enjoy humping a towel. You better keep that tongue, because it is the only reason I let you in the bed with me."

I didn't believe this to be true, but it was humiliating, and as she kept saying things like this, I got to an edge and stopped licking her, begging to come.

"No. Stop. It has not been two weeks. You better not come." She was frustrated and close to coming. "Stop humping the towel and get back to licking me. I cannot believe you interrupted me. My orgasms come first. You need to learn to control yourself."

My cock was throbbing in the wet spot as she berated me. I kept busy licking her, bringing her close to orgasm. When she finally came, I was relieved, but I did not know how many more she would want. To my surprise, that was it. One was enough today. She pulled me up to kiss her and my cock was against her pussy lips. She was kissing me and said, "Thank you for that, but you need to learn to control yourself. Have you come this week?"

"No, Mistress."

Her next question took some thought on my part. "What is the most you have edged in one day?"

I thought for a second. The most was thirty-six and I told her this.

"Thirty-six times in one day? You are pathetic. Ok, then today you have to do more. So far you have one. You are going to do forty today. First, you will go to your office and surf some disgusting perverted porn that you like and get fifteen. Second, set an alarm on your watch for thirty minutes and every time it goes off today you have to stop and edge. Reset the watch when you edge and go about the work we have to do today. I have a long list and you are going to do most of it naked, so you will edge when needed."

With that, she was up and off to start her day. I cleaned up the towel and went to my office. I quickly found some bookmarked porn and it only took me about fifteen minutes to edge twenty times. When I came downstairs naked, Julia handed me a list of chores for the day that included yard work, trash, and some cleaning. All of this was on our property so I could actually do it naked.

I spent most of the day working and stopping to masturbate every thirty minutes. Well, depending on how long it took me to edge, it would be more than thirty minutes between each edge. Two weeks of no coming had left me quick on the draw though. Most times, my cock would not even get hard before I was ready to come. I was glad when I reached 40 though — my cock was getting a little sore.

Sunday morning came and I was excited to come. Julia rolled over sleepily and traced a two-inch-long nail down my stomach to my erect penis. She smiled and said, "Someone is happy to see me. I suppose you want to come today?" She began to stroke me.

"Yes, Mistress. Please?"

"Please is good. Have you kept your promise and not come for two weeks?"

"Yes, Mistress. I have not come in two weeks"

She whispered, "How many times have you wanked your pathetic little cock?"

"176 times, Mistress," I said as I turned red. Because she was stroking me, I suddenly said, "May I please come?" I had reached the edge.

"No." She stopped touching me. "You really are a minute man. Ready to come as soon as I touch you. Not only can you not please me with that pathetic cock, you could not please any woman. Or man for that matter! Go get a towel and lick me while you hump, but you had better stop before you come. You cannot come until after I do."

I was disappointed because I was hoping to come from her touching me, but it looked like she was going to make me hump the towel again. However, I got the towel and proceeded to rush into it trying to get her an orgasm as fast as I could. She was not having it. She slowed me down and started giving directions and it was obvious she was taking it slow. Meanwhile, I was stopping every few seconds on the edge of humping a towel. I literally could only hump for ten to fifteen seconds before I would be on edge. The towel was soaked with precum. After what seemed like an eternity, she approached her orgasm and finally came in an unusually loud, screaming fashion. I stopped humping and waited for her to recover.

When she recovered, she pulled me up and I had the barest hope that she would let me inside of her. As my penis pressed against her wet pussy lips, she asked me if I wanted to be inside her.

"Yes, Mistress, please," I said.

"Can you make me come if you get to be inside me?"

"I will try, Mistress"

"Trying is not good enough. You are only getting inside of me if you can promise that you can make me come with that pathetic little cock of yours."

I wanted to be inside so bad that I was willing to risk disappointing her. I also knew that I would probably come very quickly, but I was determined to continue having sex after my orgasm to bring her to a climax. "Please let me inside of you, Mistress," I begged.

"Begging is not good enough. If I let you inside of me and I do not come, you will not be allowed to masturbate or come for eight weeks. Your alternative is to hump my leg while you tell me how much you need me. What will it be? I recommend you start humping because you really are not capable of making me come with that thing."

"Please can I hump your leg, Mistress?" I said quietly. I realized the odds of me making her come via intercourse were almost impossible. It had never happened before without a vibrator or her own hand helping on her clitoris, and I did not want to wait two months to have another orgasm.

"Yes. Do it quickly."

I moved over to her leg and started humping it. It did feel good. I also started telling her how much I needed her and wanted her. She ignored me. She looked bored, and as I begged to come about forty-five seconds after I started, she actually looked at her watch in boredom as she gave me permission to come. I screamed out as two weeks of pent-up cum gushed out of me onto her leg and my belly above it. I kept coming in one of the biggest orgasms of my life as she ignored me. When I recovered, she kissed me, and we started talking.

She wanted to know if I was OK. If I enjoyed it. I told her yes, it was wonderful and thanked her over and over. She seemed very concerned that she had pushed it too far, but I assured her she had not. This was not the easiest task. I was post orgasm and feeling my own guilt at what we had done for several weeks. I know myself well enough to know that inhibitions lost during lust are regained after an orgasm. I also knew that by later that Sunday I would be horny again and willing and wanting to humiliate myself.

I was also worried that all of this was not an interest to her and had been a turn off. I thought she was just doing this for me. I probed and prodded but she had enjoyed it. She claimed to not understand it but was willing to do more.

The rest of the day was a lovely day spent by the pool relaxing!