Crossroads

It began - of all places - with a random video on a porn site. I stumbled across the video - a solo performance by a sexy blonde transgender woman - and posted a comment on it.

My comment: "Your boyfriend must be a very lucky man. You're gorgeous."

Her reply: "I don't have a boyfriend. :( Thank you for saying I'm gorgeous."

She had a personal website. I checked it and contacted her through that. Soon we were exchanging e-mails.

Her name was Cindy. I gave her mine (Henry), and we found out about each other. We were both in our mid 40's, single, D/D free, and unattached. She was five-foot-ten, with C-cup breasts (I had that information off the porn site.). She worked as a retail associate and was barely making it, even with the money she made on the side doing custom vids for guys (and the occasional gal). I had a stable corporate job, was five-foot-eight with brown hair, and the only thing missing in my life was female companionship.

I would have asked her out if she wasn't 1,000 miles away. But I caught a break about four months into exchanging e-mails (and by then, pictures: I even had her make a custom video for me so I could help her out financially. I paid her double the normal rate.)

The retail chain she worked at was hit with a massive financial loss. They closed fifty locations, including hers. She started panicking about what she was going to do.

"Why don't you move in with me?" I suggested. I even offered to pay the costs of the move.

Four days later, on a Saturday morning, she arrived. I put her in the spare bedroom of my house and helped her unpack.

"Thanks so much, Henry," she said. "I didn't have a lot saved up, and..."

"I know, Cindy." I put a finger to her lips. "Don't think about the bad stuff. You're here now and I'm not going to let anything happen to you."

"And what do you get out of this?"

"I'm hoping to get a pretty, busty, blonde girlfriend."

"You forgot horny."

Before I could reply, Cindy pulled me tightly against her, seized my lips with hers, forced open my mouth, and jammed her tongue halfway down my throat. I wrapped my arms around her and kissed her back in self-defense. Eventually, we had to break for air.

"Is that a yes?"

"That's a yes, Henry. Now why don't you take your clothes off and lead me to your bed?"

We made quick pit stops, stripped, and climbed on my bed.

"This will be my first time with a transgender woman..."

"Just treat me like you would any other woman it was your first time with. Ask what I like if you're not sure."

We kissed again, tongues twining.

"Do you like having your breasts kissed and your nipples sucked?"

"I sure do."

I helped her slide her body upwards, and began kissing down from her neck towards her chest.

"Mmmmm. Nice and gentle."

"I'm never in a hurry when it comes to sex."

"I am, but that's because I haven't been with anyone in ten years."

"No wonder you're so horny."

I kissed slowly through her ample cleavage, trailing my tongue along her soft skin. She teasingly pressed her breasts together around my face. Then I kissed up one of her breasts to the nipple. When I took it in my mouth, she let out a happy sigh.

"It feels so good to have someone in bed with me."

I circled my tongue around her nipple, then took it in my mouth and started suckling. Her arms secured me in place. I began lightly rolling her other nipple between my fingers.

"Keep doing that."

I switched my mouth to the nipple I had been teasing with my fingers and cupped her free breast in my hand. She shivered and moaned. As I suckled with more intensity, I felt her pole stiffen and poke against my flesh.

I sped up the flickering of my tongue over her nipple. Her breathing deepened. She held me more tightly and began caressing me. I put my free arm around her and groped her butt.

"Okay, I'm warmed up now. Let me warm you up."

Cindy shifted us so that I was lying on my back. She slid downwards, kissed me again, then positioned herself between my legs.

"Let's see this thing."

She stroked my cock to full hardness and smiled as she locked her eyes onto it. Seven inches long and decently thick. I'd never had a woman complain about it and she wasn't going to be the first.

"Oooh. I bet that would fit nicely in my mouth."

I merely nodded, content to let her lead. She slipped her lips over the head of my cock and began teasing the tip with her tongue, tracing delicate patterns. I let out a soft moan.

"Glad you like," she grinned.

Cindy slid her head downwards a bit, taking about half my shaft in her mouth. She cupped my balls in her hand, softly massaging them as she slid her tongue in circles around the top of my rod.

"A nice big load in here for me."

She then slipped her head all the way down, taking my shaft to the hilt. I shuddered and my hips bucked spontaneously. She bobbed her head up and down, licking along the sides of my cock and then popping up to tease the head. I sighed with pleasure and let her work her magic.

She continued to caress my balls as she blew me. They were quite hard and filling fast. I began moving my hips, fucking her face to the same rhythm she was using.

She popped her mouth off of me. "I think you're ready."

"I agree. But ready for what? Do you prefer me inside you, or would you rather be inside me?"

"Like 90% of transgender women, I prefer to receive."

"Okay, Cindy. What's your favorite position?"

"Let's do missionary today. That way I can see your face and you do all the work."

I laughed. "Yeah, you would be tired after the move. Lie down then, honey."

We got into position, and I dripped some lube into Cindy's rear orifice. Then I slowly eased my cock into her.

"That feels very nice, Henry. I hope you have the energy to fuck me often."

"Ready for me to pump you?"

"Go for it."

I eased in and out at first, letting us both adjust, and built a rhythm. Then I made love to her, steadily sliding in and out. Her body shuddered. I leaned down and gave her a quick kiss.

"Mmmmm. You can go faster."

I sped up my thrusting. She wrapped her legs around my waist. I continued smoothly ramming in and out of her rear.

"Does that feel good, Cindy?"

Her hand had wandered down to her cock. She was stroking it to the same rhythm I was fucking her. "Yes."

"Good." I dipped my head to suckle on one of her nipples as I reamed her. Her breathing deepened and she moaned. I plowed her harder, encouraged by the sounds she was making.

"Oooooh! Keep... fucking... me..."

I began giving it to her as fast as I could make my hips move. She was now actively trying to milk the cum out of my cock. Suddenly, she climaxed, coating her belly with her cum. I was happy that I'd made her happy, and I filled her rear with my seed.

We waited a moment to recover, then cleaned up together in the shower. After drying off, we returned to the bed.

"Did that take some of the edge off, Cindy?"

"A bit. But I want to taste your cum next time."

"And how should I reciprocate?"

"You don't have to. Just let me blow you and drink your sperm."

"Are you sure? I don't want to be a selfish bastard."

"The fact you asked that means you're not. Just fuck the cum out of me at least once every weekend, like you just did."

We putzed around the house for the rest of the day, watching a couple of movies and eating when we got hungry. Cindy asked to sleep in my bed with me, and I agreed. We fell asleep with her head on my chest, and woke up in that same position.

After doing our morning routine, we got back in the bed.

"Ready for me to suck the cum out of your balls, Henry?"

"You don't have to ask. You can blow me any time you like, Cindy."

She stroked me to hardness, then got in position between my legs.

"Prepare to have all your sperm drained."

With that, she slid her lips over the head of my cock. Again, she began by tracing patterns on the head of it with her tongue. I lay still and let the pleasure shoot through my body, darts of it radiating outward from my shaft and zipping all over my skin.

Cindy took about 2/3 of my length in her mouth and began slowly running her tongue up and down. Now that the edge was off for her, she wasn't in a hurry either. Her fingertips teased my balls, causing them to gradually begin filling.

"Mmmmm. You're really good at that."

She smiled at me with her eyes, since her mouth was otherwise occupied. Then she took all of my pole into her mouth, opening her throat a bit. She sped the motion of her tongue and caressed my balls more insistently. I began to approach climax, and my moans indicated so.

As she deep-throated me, I felt my legs tense up. Cindy noticed it and lashed her tongue furiously up and down. With a grunt, I shot my sperm into her throat. She swallowed every drop, popped her head up, licked her lips, and gave me a salacious grin.

"Don't be surprised if I do that while you're sleeping. You taste really good."

I gathered her into my arms. She rested her head on my chest.

"Cindy, you can have as much sex as you want from me, of any kind, as long as we're both home. I can't have you blowing me or fucking me at work. I don't think my bosses would appreciate it."

"Fair enough," she said. "I'll need to find work, too."

"I'll help with that."

"I have a confession to make," she informed me. "I didn't have to spend ten years without the touch of a man in my bed. There were people who would gladly have taken me home for a night, banged me and left in the morning. But I didn't want to just get fucked. I wanted a real relationship."

"I'm glad I could be the one you picked for that."

I helped get Cindy a job at another branch of my company, within walking distance of the house. Every weekend, I fuck the cum out of her at least once. And several times per week, I'll wake in the middle of the night to find her mouth around my cock as it's squirting. She always swallows every drop.