Nothing Left to Lose

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Transgender woman solves lonely man's problem.
2.6k words
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I stared at the table, blankly. I glared at the empty shot glass that had contained vodka.

"What did I do to deserve this, huh?"

The shot glass did not answer.

I withdrew into my mind. A year ago, things had been perfect. My wife and I were gainfully employed. We loved each other dearly. Our friends said we were the perfect couple. We owned a small house free and clear thanks to an inheritance on her side of the family. And she had just gotten pregnant.

Two months later, the miscarriage. We were devastated. But we vowed to try again.

A month after that, she was standing on a corner waiting for the light to change so she could cross the street. A teenager who thought he was invincible took a turn too fast, lost control of his car, and shattered her leg.

She was fortunate. The teenager, not wearing his seat belt, didn't make it. The coroner said that while he *might* have survived being pitched through the front windshield, the instant his head hit the light pole he was a goner.

And then, the biggest blow of all. While in the hospital trying to re-learn how to walk, the leukemia was found. Everything was tried. Nothing worked. In 3 weeks, she was gone.

I somehow managed to go to work every weekday. But the instant I got back home, this near catatonic depression sucked me in.

I was sick and tired of being sick and tired.

I made a snap decision. I would shower, put on clean clothes, and drag my ass to the strip club. Maybe seeing the nude women would snap me out of it.

I did exactly that. And while after I returned home I still didn't feel any better, I realized that I should get out and have sex. I hadn't done that since my wife had gone into hospital.

The question was, how? I didn't feel like hiring a hooker. I wanted the sex to be meaningful. If all I wanted was a meaningless orgasm I could always jerk off.

When people in my neighborhood have problems, they go to Mama K. I should probably explain about Mama K. Five years ago, the elderly owner of a house half a block from me died. His son didn't want to own a house and put it up for sale. About 2 months later, it was bought. The entire price was paid by check at once -- no mortgage this time. A moving truck appeared and movers moved furniture and boxes into the house, and a figure in a hooded cloak, apparently the new owner, moved in. For a year the doors remained locked and the windows had their curtains drawn, although we could see lights on and a shadow moving around, so the owner was present.

Then, suddenly, invitations appeared in the mailboxes of everyone in the neighborhood. "You are all invited to an outdoor party in my back yard (321 Able Street) on June 9th. There will be food, drinks and games provided, and I can meet you -- and you me. (signed) Your new neighbor, Mama K."

The party was a fantastic success. Mama K, revealed to the neighborhood, was a buxom Latina,who appeared to be in her early 40's. She was dressed in a red top that set off her dark skin and emphasized her chest. I estimated her breasts as maybe between C and D cups. Her skirt, stopping mid-thigh, showed off her smooth, muscular legs. Her face had a permanent smile on it, and she circulated and managed to talk to all of us. "Any time any of you have a question or a problem, you come talk it over with Mama K."

And from then on, every day unless the weather was too horrible, she was seated outside, always talking to people. And she solved just about the whole neighborhood's issues.

Now it was my turn. I showered, shaved, put on shorts and a T-shirt (July is a hot month), and walked over to Mama K's house. She was lounging in her chair.

"Howdy, Phil," she grinned. "What can Mama K do for you today?"

I settled myself in a chair facing her. "I'm kind of lonely. As you know, my wife died recently. I'm depressed every time I'm at home. Honestly, I don't know what to do. I don't want to have random sex with some escort. I suppose what I really want is a companion."

"Let me ask you something," Mama K chuckled. "Have you ever seen me date in all my time living here?"

I paused to think. Mama K was always in her chair helping people out, but...

"No, I haven't actually," I replied.

"That's because no one has ever asked me out," she informed me. "Everyone comes to me for advice, and I certainly have all the social interaction I ever need. But as far as dating or romance, completely barren. Everyone likes me, but no one dates me."

"Are you all right with dating a younger man?"

"You can't be that young if you had a wife and you were trying for kids."

"I'm 28, and you must be close to old enough to be my mom."

"Does that bother you?"

"Not at all. You're a very awesome woman."

"Then, stop beating around the bush and ask this 47-year-old for a date, you goof."

"Very well. Mama K, may I take you out to dinner tonight?"

"I'd love it, Phil. Meet me here at 6."

At precisely 5:58 p.m., I knocked on Mama K's door. She emerged wearing a very pretty yellow sundress that set off her dark skin beautifully. I was in shorts and a T-shirt, as even at 6 pm it was still over 90 degrees F. We walked to the hole in the wall 5 blocks from her house.

"This place serves excellent Chinese food," Mama K said approvingly.

"That's why it's one of my favorites," I smiled. The conversation and the meal were both quite nice, and I found myself wondering why no one had asked out Mama K before.

"I had a good time," she informed me as I deposited her back at her door.

"I'm very glad," I grinned. "Shall we have another date tomorrow evening? I'll cook for you."

"Is this your way of trying to get me into your house?" she smirked.

I blushed. "Well, I suppose it would have that effect."

"You can't fool Mama K," she chuckled. "I accept. But understand that there will not be sex afterwards just because you cooked me dinner."

"Since you brought up the subject," I inquired, "what would be a way to get to the sex afterwards?" My tone was half-joking.

"Have a few more dates first," she giggled.

That seemed very reasonable. I cooked up grilled chicken, baked potatoes, a side salad and home-baked cookies for dessert.

"You are a good cook," Mama K approved.

"You inspire me," I told her.

"I know I said no sex," Mama K laughed, "but I didn't say there wouldn't be any kissing." She stood up, walked over, and gave me a short but sweet kiss. "You're not a bad guy, Phil. I honestly thought I was off dating for life."

That caught my attention. Was I going to learn a bit about Mama K's past?

"My partner, like yours, died a few years back. He was the last scion of a rich family, and left me everything in his will. That's why I was able to buy the house outright and why I don't have to work and earn money."

"I'm sorry to hear that he died."

"Got into an argument with some guys outside the Below Zero Lounge one night. Just because he was rich didn't mean he didn't enjoy the club life. That's actually where I met him, that club. But on this day, there were some rowdy white boys causing trouble. When he told them where they could stick their attitude, one of them pulled a gun. The medical examiner said death was instantaneous."

"Ouch. Did they catch the fucker?"

"They didn't have to. One of the white boys told the guy who shot that he'd crossed the line and shot HIM dead on the spot. The security camera at the entrance door caught the whole thing. Then the remaining white boys hightailed it out of there."

All I could say was, "Wow. That's crazy. And sad."

"And that is when I got the hell out of Ohio and came here," Mama K concluded.

I hugged her for a good few minutes. She had just revealed a very painful part of herself to me. That showed a lot of trust.

After I returned her to her house, I went online and found some news reports about the incident. It had indeed gone down exactly as Mama K had described it. The next evening, I told her about my research.

"And you still want to date me, and eventually have sex with me?" she asked.

"Yes on both," I replied. "You're very nice and a beautiful woman."

"And you're very sweet," she responded.

Our next date was at a public park. It was fun holding Mama K's hand (and kissing her about once every 5 minutes) as we sat on a bench. We purchased food from one of the vendors and called it dinner.

We went to a play next. The Mountain View Performing Arts Center was about a mile off, and we walked it. The play -- "Big River" -- was based on The Adventures Of Huckleberry Finn, and was greatly enjoyable.

Mama K was able to pull some strings the next weekend and get two tickets for us to see Garrison Keillor do a live show. The outdoor amphitheater was packed. We laughed so hard that I thought I was going to crack a rib. "I'm glad you enjoy this kind of humor," Mama K told me. "Most young people wouldn't."

The opera was next up. I had never been to one. Mama K had picked a comic opera -- "Falstaff" -- about a very NOT noble knight. The English translation of the sung Italian was projected on a screen above the stage for the audience to follow along. And I finally found out what "comic opera maneuver" meant.

By now we were into September. Mama K and I still hadn't gone farther than kissing, but we were now doing deep kisses with lots of tongue action.

"I think we're ready to take our relationship to the next phase," Mama K told me. "Next Friday night, come to my place and I'll cook for you. And you've been very patient about the sex. After dinner, we'll go to my bed."

It came as absolutely no surprise that Mama K was an excellent cook. Everything else about her was perfect, so why not her cooking skills as well? I said as much, and she blushed.

"You don't need to flatter me. I've already agreed to have sex with you tonight."

"It's not flattery if it's true."

We finished up, took the dishes to the kitchen, and entered her bedroom. Both of us stripped. Hers was about the same size as mine.

"Nice equipment," I told her.

"You're not surprised," she observed. "How long have you known?"

"Since you mentioned what happened to your partner. That club doesn't normally have women in it."

"And you're OK with physical intimacy."

"Mama K, you are gorgeous. I'm more than OK with physical intimacy. And this explains why you waited a year to show yourself."

"Yep. I've known since I was a teenager, but it wasn't until after my partner's death I had the money to transition."

We lay on the bed, and started with yet another kiss. But this time, after we broke the lip lock, I kissed Mama K's neck. That drew a shiver.

I kissed and licked at the sensitive spots on her neck before slowly progressing my lips towards the very top of her chest. I wasn't in a hurry. I lingered at the spot where her breasts joined her torso. Then I kissed around the base of each breast before tracing a slow helix with my tongue up to her nipple. I repeated the process on her other breast, then began sucking her nipples. That drew a soft moan.

I worked her breasts for a few minutes longer, then pivoted my body 180 degrees so that my head was near her feet. I began kissing and caressing her lower legs, and she took the opportunity to do the same for me.

Eventually, I was kissing her legs and massaging her feet. Her skilled hands were massaging mine as well. We stayed like that for a bit, exploring each other. As I gradually worked my way upwards towards her thighs, her sensual touches and kisses caused my pole to stiffen. Hers had done the same.

We lingered some more when we got to kissing each other's thighs. We knew we were close to being in a 69, and that's where this was leading, but neither of us wanted to rush. Soft, sensual caresses and tender kisses got us both worked up.

Eventually, we did indeed find ourselves in said 69. I had never given oral stimulation to a penis, and Mama K seemed to read my mind. "Just follow my lead and let my body's reactions guide you."

I did exactly that. Her tongue circled around the head of my cock. I duplicated the movement with hers. She gently slipped her mouth down onto me. I opened and took just the bulb of her inside me, gently stimulating it with my tongue. She took more of me in, using her tongue to slide up and down the quivering shaft. I took as much of her as I could and used my tongue to give her pole pleasure.

She broke suddenly away. "Your mouth does feel wonderful. But I want you inside me."

Mama K lay on her back and spread her legs, after first slipping a pillow beneath her lower back. I gently worked my cock into her bumhole until I was in all the way. I began a slow rhythm, pumping in and out.

"You can do me harder, Phil," she whispered.

"Okay," I replied. I sped up my hips. Mama K's body quivered as I pounded in and out. "Mmm. You are so tight. If I don't slow down you're going to make me cum."

"Fill me with your cum," she panted. I proceeded to squirt hot jets of seed into her rear. Mama K smiled as I withdrew my softening cock from her hole.

"You didn't climax," I sighed. "I want to make sure you have a happy ending."

"I was just saving it for the next phase," she grinned. She dripped some lube onto her cock and rolled me onto my back. "I'll be gentle."

She was. She let my back channel adjust to being filled with her pecker. Then when she did start pumping me, she took it slowly. It did feel good,and if I hadn't just cum I'm sure I would have gotten hard. Mama K was very hot, and it didn't take long before she injected my ass with her seed.

"Now we're both satisfied," she purred.

"So we are," I laughed. We showered up, dried off, and returned to her bed. We lay still, snuggling against each other.

"I wouldn't mind doing this much more often," Mama K murmured.

"Any time you like, dear," I whispered.

It was a few months later when Mama K bought my house, moved me in with her and rented where I used to live. I was OK with that, as the place had a lot of bad memories. Living with Mama K, on the other hand, we made a lot of good ones. I quit my job and Mama K now had an assistant during the day to solve the neighborhood's problems. While at night... fun times.

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4 Comments
AnonymousAnonymousover 6 years ago
Coud have used a better name.

Coud have used a better name for the woman or had her reveal her real name after some time. Description of sex coud have been better too.

YIAYYIAYalmost 7 years ago
Pretty good.

I wish the story was more longer. 😟

HarleyRider228HarleyRider228almost 7 years ago
Very nice story

I especially liked that there was an element of friendship becoming love to the story. This wasnt a simple one dimensional wham-bam thank ya ma'am story. He accepted her as a good woman not a hot transwoman.

DianeRedfernDianeRedfernalmost 7 years ago
Sweet and Lovely

Inspirational story of why you never give up on your dreams, your goals and being who you really are and need to be. Just love that this is a true love story with little emphasis on outfits and sex to interrupt the flow of the sadness both endured turned to joy. Just love it.

xoxo,

Di

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