My Life In Three Acts

With her breathing picking up, I moved to her boobs, placing my hand on her still growing cock. As I slid my hand up and down her cock, I sucked a bit harder on each nipple.

As my hand had her as hard as I thought she'd get, I moved down, taking her sex in my mouth and started bobbing up and down. She got even harder and finally with me gently cupping her balls, I knew she was nearing an explosion.

Hearing her breathing turning to outright screaming, I felt her cock starting to throb, shooting small streams of cum right down my throat. Her body still shook for a few more minutes, until her breathing finally started to calm down.

"Oh my fucking goodness, Jenny, I've never felt anything even close to that feeling."

Looking over at her, I saw she was still fairly hard. Taking her in my hand, and moving one leg over and sliding her cock into my very wet pussy. I started moving up and down, realizing she was at full staff, again.

Getting into a nice rhythm, she started thrusting upwards, along with taking my tits, one at a time and sucking softly on my nipples. God, this t-girl was fucking me almost as good as Jack used to. Or just maybe, it felt so good because I'd done without for so long.

When she finally came, again, I had already had two very nice orgasms. Rolling onto our backs, we just looked each other in the face, with Erin wiping a few tears from both eyes.

"Do you think you can do this with your new girlfriend?"

"God, I hope so, Jenny. Are you sorry we did this?"

"Not a chance, my sweet Erin."

After a very nice couples shower, we dried off and had a very nice conversation about what we had done together.

We talked about what we had done, that after thinking for a while, I didn't have any regrets. Yes, I had sex with a transgender girl, and absolutely loved it. She actually made me cum a few times, and I hoped I had instilled some confidence to be used with her new girlfriend.

ACT THREE: Mature

For several weeks after my little tryst with Erin, I started meeting more people in my new neighborhood. The one thing I noticed was the majority of men were fairly old. In their 60's or 70's.

I knew I wasn't that desperate, so I kept a fair distance from the few single men, who lived near me. I did talk to a couple of these men, and quickly realized they wanted a nurse, not a girlfriend.

There was this one geezer who actually told me to let him know when we could go out to dinner, so he could take his little blue pill, just in case. That dinner never happened.

One day, as I was walking around our closest grocery store, I nearly bumped into a young man, who looked to be in his mid 30's, at most. He also had a little girl about four or five years of age with him.

After leaving the store with a little smile on my face, I happened to see him in my area, a few days later, just walking around, again with this cute little girl.

"Visiting, here?" I asked.

"No, Ma'am, we just moved in up the street. This is my daughter, Leah."

"This is my daddy, Lee," she grinned.

"Jenny Green, and I'm happy to meet both of you. Please Lee, its just Jenny. Leah, the next time my grandkids are over, you could play with them, as there aren't too many your age living here."

Both of them grinned, saying that would be nice.

I didn't want to ask where her mother was, just in case.

Lee must have been psychic, because he quietly gave me some added information as we kept walking down the street.

"Lee Wilkes, and her mother got tired of my military service, and up and left over two years ago. When I finished my full twenty, I retired and moved back home."

"Marines?" I asked.

"Yes, I was infantry, but mainly an instructor."

I then took a closer look and noticed how well put together this man was. Right around six feet tall, 180-185 or so. Not an ounce of fat, anywhere, still with his Corps crew cut.

I noticed Leah whispering to her father, when he said for her to ask for herself.

"Mrs. Green, when will your grandkids be visiting, because I'm kind of bored."

"First off, you can call me Jenny, and I'll make sure they will be over next Sunday."

I never needed an excuse to have any of them over. I made a mental note to have Brianna come over with her family.

When we reached my house, we said our goodbyes and I went inside. I started to reason with myself. If he had served twenty years in the military, he might have been older than I had figured. I then asked myself if I was so lonely that this man and his lovely daughter were a figment of my imagination.

The following afternoon, when I was walking, I noticed Leah with an older lady. She ran up to me and told me this was her Nana, who was staying with them.

"Jean Wilkes, and I've heard about you from Leah. I guess you made quite an impression, telling her about your grandkids visiting in a few days."

It must have been the third day in a row, not seeing Lee, I wondered if he might have been avoiding me. I realized that I just might fit into the desperate category, having just met this nice, young man.

On Saturday, there were the both of them walking towards me, when Leah ran up to me, asking if my grandkids would be there, tomorrow.

"Yes, and I'd like to invite you all for lunch, if that's OK with you."

"That's fine, but my mother has a previous engagement and won't be joining us. She has a boyfriend who asked her for a Sunday brunch. But we'll be there."

We just walked a couple of blocks, talking, when I decided to get real brave.

"Lee, if its not too personal, can I ask how old you are?"

Laughing, he told me he was forty-two, and he was used to being asked.

"Jenny, please don't take this wrong, but I've been hired by the Community Center down the street to teach a health and fitness class, and if you know anyone interested, you could spread the word?"

My first thought was why on earth with this gorgeous young man want to watch a bunch of old ladies work out. But I realized that he needed a job, and this seemed to fit his talents.

Brianna, Jim and their two kids came for lunch. While the kids were in my back yard playing, we all noticed Lee was very quiet.

"Penny for your thoughts, Lee," I asked.

"Nothing, just my ex ruffling my feathers."

"If I may, can I answer any questions, as I'm a lawyer," Brianna said.

They started talking, actually Lee talked and Brianna listened.

It seemed as if his ex wanted custody of Leah, most likely to get Lee to pay her child support.

After a few more questions, my daughter told him she would ask one of her colleagues who knew quite a bit about military law.

"Lets all have some lunch, then we can talk some more," I said.

After lunch, the kids played some more and Brianna took down some more information. We could see my younger grandson was getting tired, so they started gathering them together to leave.

Saying their goodbyes, my daughter told Lee she would be in touch in a day, or two, and the kids all said they couldn't wait to visit.

As Lee and I just started talking, we noticed his little girl sound asleep on my sofa.

"I guess your two grandkids wore her out."

"I can't thank you enough for having us over, and please don't think I mentioned that class meaning you were in need of a healthier lifestyle."

"I know I need that, but might not have, um, oh, shit, I don't own the proper bra to keep these from bouncing."

Seeing him blush, he took his phone, looked at something, and sent it to mine.

It was a website for workout clothes for women, that had a section for full figured women.

Finally getting up to leave, he thanked me again, and very softly kissed my lips.

Now it was my turn to blush.

Off they went with the feeling of a man's lips on mine, if only for a moment.

I did start taking Lee's fitness class, armed with the appropriate clothing.

Even with a very strong sports bra, I felt I just jiggled a bit too much. I overcame my embarrassment seeing some of the other ladies having similar issues.

I did have to admit to enjoying Lee's touching when showing proper placement during our light exercising.

It didn't hurt seeing him in a tight tee shirt and shorts that didnt quite come down to his knees. I hope he didn't catch me glancing at his crotch, trying to guess what was in there.

A few of my lady friends discussed this after each class, so I just let them talk, while I dreamed.

Into our second month of classes, he was waiting in his little office, and asked if he was out of line, asking me to dinner. He did mention it would be just the two of us, with his daughter being watched by grandma.

I took a breath or two and told him I was OK with that. I had this smirk the entire week, waiting for my dinner date.

As I did many nights, I quietly asked Jack if it was all right with him, as it seemed to skip my mind carrying on with Erin.

He told me he was fine with it, and he was also fine with the other hijinks.

The Thursday before our dinner date, Lee told me he had a hearing to deal with his ex and her attempt a full custody. I asked him if he wanted company and he finally agreed.

We drove to court separately, and when I saw him outside of court, I must have had a stunned look on my face.

Dressed in his finest dress uniform, with rows of medals, and shoes so shiny you could see yourself, he was even more impressive.

Preliminary Hearing:

Judge: Let's come to order in the custody matter concerning Leah Wilkes, a minor.

Harley Jenkins for the applicant.

Brianna Green for the respondent.

Your Honor, Ms Ball wants full custody of her daughter, Leah. We intend to show that Lee Wilkes isn't a fit parent.

Your Honor, We will show that Shelly Wilkes, or is it Shelly Harris, or Shelly Wilson, or even Shelly Ball as she's now calling herself, is the unfit parent. I'd ask the court to inquire how Ms Ball thinks she's fit to care for Leah, when she doesn't seem to care for her other children, Karen, aged 17, Curtis, aged 16, and

OBJECTION!

Sit down counselor.

And Owen, age 14.

I sat there even more impressed with my daughter than ever.

Ms Ball, would you care to respond to Ms Green's question?

No, your honor.

Case dismissed!

As we left the courtroom, smiling, we noticed Shelly leaving with her sleazy lawyer. I remember hearing about this jackass over the years, and had a good idea how she was paying his fee.

Standing in the lobby of the courthouse, Brianna quietly told us that should be the end of this matter, and left Lee and me standing there just smiling at each other.

"Dinner still on for tomorrow," he asked.

"Of course, but dressed like that you'll scare everyone half to death."

"I just can't thank you enough Jenny, you've been such a friend, I don't know what to say."

"A nice dinner conversation will do just fine," I grinned.

Our dinner at a nearby restaurant went very well without a word of the court proceedings from the day before.

I could tell that something was bothering Lee, but couldn't put my finger on it.

"Sonething's bothering you, isn't it?"

"Yes, and let me finish, before answering. My daughter is staying with my mother at her boyfriend's house tonight, and, umm, oh shit, I really suck at this, but would you consider staying the night, with me?"

"Only if you're positive you truly want me to. And just so you know, beforehand, I've only slept with one man in my entire fifty-one years."

There was no way I was going to tell this charming man about my onetime fling with Erin.

"Yes, I'm sure, and I will be a perfect gentleman," he said with a wicked little grin.

I had a long conversation with both my girls and my daughter-in-law, and all three of them told me it was about time, and for me to just test the waters. When I told them about my lack of experience, they all reminded me of jumping in the sack with Erin and having no regrets. With a smile on my face, I took their comments to heart.

Our dinner couldn't have gone better. We kept our conversation light, and we just enjoyed talking to each other.

Getting back to his house, he took my coat, and led me to his living room. Just sitting, with him holding my hands, we moved next to each other. I took his face in my hands and softly kissed his lips. He took my face in his hands, and returned the kiss.

I have to admit, my nerves from the past week were starting to calm down. I had several discussions with Jack who told me this was more than OK with him. I just felt a bit guilty enjoying it so much.

Moving slowly towards his bedroom, my nerves started to kick in again.

I moved in front of him, slowly unbuttoning his shirt. Taking it off, I stood back, while he lifted my sweater up over my head. I'm not sure what he was thinking, seeing my huge bra covered boobs, but they brought a smile to his face.

We both started removing our remaining clothes. My skirt. His jeans. My bra. His boxers.

My goodness was this man put together. It took me a moment or two to realize what was so different. As I was lowering my panties, I realized I had a foreskin to deal with.

Not saying a word, we moved onto his bed, laying next to each other. We gently kissed, as one of his hands gently caressed one of my breasts. My nipple was as hard as its ever been.

When I reached his very large manhood, I moved my hand up and down his shaft, hearing his soft moans, I knew I was doing something right.

He moved his attention to my other breast, making that nipple stand up and take notice. I started to feel the moisture in between my thighs in anticipation of what was to come.

Rolling me onto my back, while still kissing me, he slowly slide his considerable girth inside my already drenched pussy.

My mind was racing, as both his kisses and thrusts picked up their pace, my body was on fire. I quickly wrapped my legs around his behind, as he picked up the pace, even more.

My fingertips were digging into his back, as I felt him explode into the very depths of my insides.

I think I frightened him a bit, when my tears of joy started. I noticed he was still nearly at full staff, so I kept my hips thrusting upwards enjoys his still hard manhood filling my cunt.

He redoubled his thrusting, but now, instead of just shaking, I was moaning and at the point of him exploding deep inside of me I was literally screaming.

I had experienced a very satisfying sex life for twenty-seven years with my beloved Jack, but this was something different, altogether.

As I sat in the bathroom, cleaning up, I just couldn't stop crying. After a few minutes, Lee came in and silently took me in his arms, carrying me back to his bed.

Putting my nightgown on me, and holding me very close and letting me get the tears out of my system.

As his arms held me close, and his whispers tried calming me, I started feeling just a bit better.

"Was it that bad?" he asked.

"No, dammit, it was fan fucking tastic! I wasn't supposed to enjoy you that much."

Or at least that's what I tried thinking to myself.

"Do you want to go home?"

I just shook my head no, knowing if I was alone, I'd feel ten times worse.

"No, I need to be held just like you're doing right now."

Just feeling his muscular arms around me, had a calming effect. Feeling his body's reaction to me being so close, I couldn't believe what I was feeling. His cock was nearly at full strength.

"Shush, and please don't say a word."

I started by lightly kissing his lips. While doing this, my hand was lightly pinching his nipple. First one, then the other. I then leaned down and kissed each one. I felt his cock up against my body, and moved further down.

Finding him at nearly full mast, I took him in one hand, gently slid back his foreskin, and kissed its mushroom like head. Hmm, no difference in taste. God, it seemed to grow even bigger.

Just as about half his tool went into my mouth, he moved my body just so, and started licking up and down my swollen cunt lips. When his tongue swirled around my clit, my entire body shook, with nearly two thirds of his sex in my very warm mouth.

He then slowly inserted two fingers into my throbbing sex, causing a fantastic orgasm, and me letting his cock leave my mouth, for fear of me biting it.

No sooner than my excitement lessened, just a bit, I swung my body around, impaling myself on top of his glorious manhood.

Leaning over to continue kissing this man who I was truly falling for, he started thrusting upwards and taking each of my super excited nipples in his mouth, one at a time. I hadn't felt this sort of excitement in well over three years.

With my body literally on fire, he filled my core with another huge amount of baby making material. Luckily, I was long past that stage of my life.

Laying back in bed, in my new lover's arms, he quietly asked if I was feeling any better.

"Lee, you've given me more excitement that I've experienced in three or four years, and I'm hoping this might be the start of something we can build on, if that's what you want."

"My dear Jennifer, I'd like to think we really have something special, because you know Leah and I are a package deal."

"I know, if we really have something, I'm going to have to help you raise a very active little darling. I just hope I'm up for it," I said with a huge grin.

We fell asleep in each other's arms. During the night, when I had to make my nightly pit stop, crawling back under the covers, I felt his cock up against me, yet again.

I started thinking, if at my age, could I keep this wonderful man satisfied. I needed to talk things over with my girls. This was bringing back fantastic memories of when Jack and I just couldn't get enough of each other, and would fuck at every opportunity, sometimes four or five times a day!

After a delightful breakfast, and talking about our future, or even if we had a future, Leah came bounding in the front door, followed by Grandma Jean.

I could tell Leah missed her daddy and Jean asked if she could talk to me in private.

I wondered if I was in trouble.

Quite the contrary. She gave me the lowdown on Lee's failed marriage.

It seemed like what started out as an idyllic marriage turned very sour about the time Leah turned a year old. His wife just didn't want to be a mother, and started screwing anyone on his base with a cock. She even started having affairs with some of the other wives.

When I asked her about her older kids, she told me they were with their fathers, and Lee didn't know about them, until his divorce. By the time the military court ruled he found out he could retain most of his pension, due to her many misdeeds. He knew he had to retire in order to devote the necessary attention his little girl would require.

"Jenny, you might be the best thing for him, ever."

"Doesn't our age difference bother him?"

"No, it truly doesn't. Plus Leah absolutely adores you."

I had a lot of information to think about. Yes, I did love the sex and our time outside of the bedroom has been more than pleasant. It has taken him some time to trust, being burned by his ex. I truly hoped the relationship with both his mom and daughter, which was very good, was a plus for me.

I asked Lee for a late morning lunch, knowing his daughter was in school, hoping just to talk.

Sitting in my dining room, eating our lunch, we both we a bit nervous. When we started, we asked each other if we were moving a bit too fast.

"Jenny, are you saying you don't want to continue in any way?"

"No, but the speed which we've been moving sort of scares me, that's all."

Holding my hands, he told me that I might have been the best thing that's ever happened to him. He also said, my relationship with his daughter was the biggest plus, but if I thought we were moving too fast, he'd step back.

I couldn't believe what I was hearing. We had only known each other for a few months, but I was fairly certain I didn't want him to step back. I just had to figure out how to tell him this, without chasing him away.