Comfort

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Lonely man, horny transgender woman link up.
1.4k words
4.32
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I locked eyes with my girlfriend. "You know where the lipstick came from. You were there, not an hour ago, when my mother tried to greet me with a kiss and missed my cheek. She was so out of it that she got my collar."

"I know that. I saw it happen. But how do I know someone else's lipstick wasn't there first and your mother's lipstick didn't cover it up? Prove that didn't happen."

"How the heck am I supposed to prove a negative? The only way to tell would be for you to have observed my collar before we arrived and seen nothing."

"I did, but just because I didn't see anything doesn't mean nothing was there."

"Yes, actually, that's exactly what it means."

She slapped me across the face, hard. "I can see you can't be trusted. I'm leaving now, for good."

She stomped out of the apartment and slammed the door behind her. Luckily, we'd only been on a few dates and none of my stuff was yet at her place, or her stuff at mine.

"Good riddance!" I told the door. I deleted her contact information from my phone after blocking her number. Crazy jealous bitch.

Sure enough, the next day there was a note in my mailbox. "I tried texting you three times. Why are you ignoring me?"

I responded with my own note in hers. "You said we were done for good, and I took you at your word. Bye forever."

Her reply: "I can find someone else."

Good, I thought. Though not for the poor sap you sucker into dating you.

I was very glad to have dodged that bullet, but it left me without a girlfriend. Two Friday nights later, I decided to stop in at the local bar. I don't drink alcohol, but a tonic water, I figured, might help ease some of the aggravation I felt.

I had taken three sips, and watched 5 game minutes of the college basketball game on TV, when an older woman - I'm 27, and this woman looked to be maybe my mom's age - sat down at my table.

"You look as miserable as I feel. I'm Stephanie."

"Michael," I replied, shaking Stephanie's proffered hand.

"Want to talk about it? Misery loves company, you know."

Stephanie's hair was a color of blonde that's only found in a bottle. She was tall, slim, and her dress exposed just a hint of cleavage. I estimated her breasts as between a B and a C cup - not huge, but they looked quite firm. Her oval face had a bit of a frown on it.

I shrugged. "Woman trouble. She broke up with me a couple weeks ago, and it turns out she was a super possessive jealous type."

Stephanie sighed. "I know the feeling. My ex broke it off with me a year ago and I haven't been able to find a man who will stick around."

"Sorry to hear that. You're pretty, even with the frown."

"You really think I'm pretty?"

I looked her up and down. "From what I can see, yes."

She stood up and walked over to my chair. "Now you can see all of me."

Her legs were long and toned. "Actually, I can't. Your dress gets in the way."

She lightly punched me in the shoulder. "You are technically correct - the best kind of correct."

I locked eyes with her. "Were you looking to take me to your bed tonight?"

"It would probably do us both good."

30 minutes later, she was giving me the tour of her apartment. it looked a lot like mine, same cookie-cutter block, and close to the same size. We both made a quick stop in the restroom before heading to her bedroom.

"No reason to waste time," Stephanie proclaimed. We both quickly stripped. Her equipment was smaller than mine.

"Does it...?"

"Technically, yes, but it's not something I use. I'm still trying to get GRS, but it's a real pain to deal with all the paperwork and the agencies."

"So..."

"So, don't expect me to use it on you."

"Gotcha." We climbed onto the bed and kissed. The first kiss was soft. The second was deeper and we twined tongues.

"Mmmmm. I need this, Michael."

I kissed her again, and this time we practically stuck our tongues down each other's throats. We only broke the kiss so we could breathe.

"So do I, Stephanie."

I kissed her neck, nibbling gently at her flesh. She giggled and pressed up more tightly against me. I traced my tongue in a slow pattern towards her chest.

"Keep going."

I did just that, my lips and tongue moving downwards towards her cleavage. Her body shivered slightly.

"Don't make me wait."

I obediently lifted my head and took one of her nipples in my mouth, suckling softly. She secured me in place with her arms as I switched back and forth between her breasts.

"That feels wonderful."

I caressed her long legs as I suckled. I could feel the little pulses of pleasure I was giving her shoot through her skin.

Stephanie suddenly rolled over, leaving me on my back. She disengaged my head from her chest and slid downwards.

"My turn."

I lay still and let her kiss from my neck to my chest. It did feel nice to have her tongue run across my flesh, and I let out a moan as she scraped her teeth over my nipples.

I felt Stephanie forcing my legs apart with her hands. Then one of them began massaging my balls while the other one wrapped around my stiffening cock. I closed my eyes and let the feeling of pleasure she was giving me flow through me. She continued to kiss my chest while she stroked me to my full length.

"I think you're ready."

Stephanie repositioned her body between my legs. Her tongue slithered its way around my ball sac as she continued to steadily stroke my rod. I moaned softly.

"I love making a man moan in pleasure."

Her hands came off my pole as she took the head of it in my mouth. She slid her tongue in circles around it, and I shivered.

"Ooooh, Stephanie..."

She slipped her mouth downward and took almost my entire length inside. Now her tongue was sliding up and down the shaft, making me twitch and throb.

"Mmmmmph!"

The noises I was making encouraged her. Her hands returned, this time teasing my balls with her long fingernails as she bobbed her head up and down, sucking greedily on my pole.

"Uffff!"

Stephanie popped her head up suddenly. "I want you inside me. Fuck me from behind."

I wasn't about to refuse that invite. She positioned herself on her hands and knees as I got behind her. I carefully worked my stiff pole into her tight rear.

"I'm not made of glass, Michael. Deep and hard."

"Yes, dear."

I began building a rhythm, sliding in and out, making sure I thrust as deep as I could with every stroke. Stephanie was now the one moaning with pleasure. She pressed her torso downward, thus making her sexy, muscular rump press back further against me.

I grabbed her hips to steady myself and sped up the motion of my own hips. Stephanie was moving in rhythm with me now. I rammed my pole into her as hard and fast as I could make my body move. In between gasping pants she screamed for it to be deeper, faster, harder.

I did my best to accomodate this woman in heat. She pressed her ass as far back as it would go on my pole. Then she let out a cry of pure lust. My balls tightened and I managed to gasp out that I was going to cum.

"Fill me up!" she moaned. I did just that, squirting hot jets of sperm deep into her back channel. Her body quivered wildly and she collapsed face-down onto the bed. I rolled off her after my balls had been emptied and lay still, breathing hard, trying to get air back in my lungs and oxygen to my muscles.

A few minutes later, after we were both recovered enough to speak. Stephanie rolled over so I could see her face and gave me a smile. I noticed a small wet spot beneath where her crotch had been.

"Yes, you made me cum too," she grinned. "Thanks, Michael. I really needed that."

"My pleasure, Stephanie."

We staggered to our feet, cleaned up in the bathroom, removed the cum-coated top blanket from the bed, and climbed into it. Stephanie pulled me against her and rested my head on her chest.

"If you spend the night, we have all day tomorrow to do more."

"And all day Sunday after I spend tomorrow night with you in this bed."

"I like how you think, Michael."

She turned out the light, and I snuggled against her and closed my eyes...

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SiamKittSiamKitt11 months ago

Love short, realistic/believable stories..This one was enjoyable (how about a pt 2..?) BUT..the guy leaves the bar with a leggy woman, & ends up in her bedroom without any real gender questions or issues..seems a section was missed out there..But hey-ho, I still enjoyed it..thank you.

Michael56SmithMichael56Smithover 5 years ago
World needs more Stephanies

A luck guy finds a gurl, the sexy gurl puts out right away. Such luck, in a sweet work of erotic fiction, makes for a lovely short tale of lust and a mutual end of loneliness for our two lovers. Cool!

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