My New Life


I was married to the same woman for 30 years. Now on my own, disappointed, but committed to creating a life that I wanted. What do I want?

Moving from suburbia, I bought a house in the city, surrounded by 30 somethings with tattoos and piercings. "WOW! This is different," I would mumble to myself over and over again. I could walk to restaurants and stores, hear live music from the sidewalk and people watch. I liked my new life!

What else did I want? From silverware to bath towels, I was crafting my life from scratch. I decided that I would only buy quality and not worry about quantity. So All-Clad pots and pans, thick and soft turkish towels, leather Lazy-Boy and high-def televisions. I began to enjoy myself giggling that in setting up house I was getting in touch with my feminine side.

I made it a point to smile and greet everyone. One by one I met the neighbors, an author, a songwriter, a student, an accountant, a musician, an historian - a very interesting group of people. I was invited over for drinks and quickly felt like part of the neighborhood. Life was good...

Being alone for the first time in my life was both fun and sad at the same time. Ever felt that way? I wanted another relationship but didn't want to risk finding another alcoholic or nut case. I just wanted someone that I could trust and enjoy. Someone that I could count on and be myself with. No more co-dependence and frustration. I had to make decisions and focus on myself. I surprised myself by coming to the conclusion that I was OK with a special person being a man or a woman.

I filled my time buying things for the house and selling away the few possessions that reminded me of my past. I sold a few items on Craigslist and became intrigued by all that I found there. I was fascinated by the personals. Shocked, I laughed out loud at the seeming outrageous requests for encounters. Day after day I returned to the postings and learned the new vocabulary, NSA-No Strings Attached, HWP-height weigh proportionate, Blow-N-Go, obviously, this was a whole new world awaiting. Casual sex, sex without consequences, sex just for fun! Nothing like this was ever part of my life!!

I read every ad in every category, day after day, fantasizing every scenario. I was drawn to the cross dresser and transvestite ads. Looking at the pictures, my heart would race and my face would become flush. I was afraid of these new feelings but very captivated by them. At 6', 200 pounds, and a shaved head I was anything but feminine!

While shopping, more than once I would grab a pair of nylons or panties off the shelf, blush beat red, and then put them back giggling. What was going on?

One day while working from home I was bored and got on Craigslist. I saw an ad from a guy in my neighborhood looking for a hosted jack off session. That seemed safe and innocent enough. My house, no worries of STDs, what the heck? I jack myself off, what would it hurt to jack someone else? Nervously, excited, and with little beads of sweat running down my back, I responded. Stunned, I received a response within minutes. He wanted to see a cock picture. I can't describe how hard I laughed, a cock picture?

OK, why not? Now I'm all in. Grabbing my iPhone I went into the bathroom and got naked. Experimenting, I discovered that the flash could blot out my face when properly positioned. Tingling with excitement but too nervous for a hard on, I settled on a full frontal pose and sent it off to my new friend. I remained naked, prancing about being silly, wiggling my ass like a chick and giggling like a school girl.

The rest of the day passed without a response. I was devastated. He must not of liked the pic. I convinced myself that he didn't like me. Sadly, that night I drank a full bottle of wine.

Mid-morning on the next day an email from him arrived, asking if I was available right now. With my heart racing and hands shaking I responded, "Yes."

His response caught me off-guard. He had a very specific fantasy that he wanted me to fulfill. He wanted to walk into my house and find me naked, jacking off to porn. Additionally, he wanted heels, hose, panties and bra available. I was breathless! My heart thumped almost painfully in my chest heaved for air. My mind wandered to those times in the store when I failed to have the courage to buy those things and now I needed them.

What to do? I really wanted to please him and I really wanted to get together with him but had nothing that he wanted. I replied with the truth and although disappointed, he agreed to come over and "...try me out." If we clicked, I agreed to go out and make the purchases necessary to support his fantasy in the future.

OMG! What did I just agree to? Nervously, I straightened up the house and took a quick shower. Shivering with anticipation, butt naked and short of breath, I settled on the couch with my Mac, looking at YouPorn. When the doorbell rang, I froze.

I cracked the door open to find a bearded 6'3" young man who looked as nervous and scared as I felt - that was comforting, he didn't seem like a nut job. Somehow, I managed to mumble "HI," and open the door. Wearing only a t-shirt and cotton shorts, silently he walked in. Without saying a word he turned to me and pulled down his shorts, slowly rubbing his almost hard penis that seemed a bit small for his height.

Awkwardly, we stumbled a bit finally settling next to each other on the couch watching YouPorn with me naked and him with his shorts around his ankles, both rubbing ourselves slowly.

"This isn't working for me," he blurted out.

Panicked, I reached over and grabbed his cock,fumbling, finally working it firmly, pretending to know what I was doing. "Is this better?" I asked softly as he began to moan. I wanted to please him.

Confused, not knowing what to do, I thought to myself, "Well, what would I like if I were him?" I'm guessing that he might like the same, so with my other hand I softly stroked his upper thighs, just like I do to myself. He moaned some more and sank a bit into the cushions. I squirted some lotion on to my palms and got back to business, he seemed pleased. I was enjoying myself too.

As I pumped, his cock grew and became very hard. It seemed to be a bit smaller than mine but still a perfect size to play with. Right hand squeezing and pumping, left hand gently squeezing his balls I stopped blushing and started smiling. We made momentary eye contact and he said, "You like doing this, don't you?"

"Yes," I replied with the heat returning to my face, embarrassed. "Seems that you do too."

"You need to dress up for me," he said assertively.

"I know, I will. This is fun," I said pumping faster as my breath became shorter and my heart raced, thumping heavily.

"You need to kiss it," he said matter-of-factly, gently pushing my head toward his lap. "Do what you're told," he coaxed softly. I did.

I got down on my knees in front of him and kissed the tip. Then I kissed it some more. My entire body was on fire! "Lick it, lick it." I ran my tongue up and down his hard shaft, up and down.

"That's it, that's a good girl," he whispered guiding my tongue by my ears. I was intensely humiliated, breathless and totally willing to do whatever he wanted. With all of the emotions overtaking me, surprisingly, I found myself to be comfortable, calm and still the most excited I can ever remember.

"Take it all in, all the way, go ahead," I needed no more coaxing. In it went, all the way. It barely touched the back of my throat so I was happy because I thought I might gag. No gagging here, I was up and down that cock like a girl possessed. I was really happy to feel him squirming. I thought to myself that I seemed really good at this.

Mumbling, he asked, "Do you swallow like a good girl?"

Swallow? I was not prepared for this so meekly I said, "I never have."

"You will," he said confidently, "but today doesn't have to be the day."

Smiling, staring at his hard cock, a leaned back on my calves and pumped away. Ultimately, he screamed out loud and shot all over my hands. We both laughed as he came.

Grabbing a towel, I cleaned him off in the nervous silence. Immediately, he stood up proclaiming, "I'm married and have a lot to lose. If we see each other on the street pretend that you don't know me, got it?"

"Got it," I said meekly, disappointed. What was I expecting?

"Get yourself some nice girlie things. I like satin and lace, big heels and stockings and don't forget the wig! I don't want to see that bald head!" He turned and left.

Hmmmm, "I guess I have a boyfriend," Laughing to myself. And he seems quite bossy!

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