Seth and I have been friends since high school. We both married in our early twenties to our high school sweethearts. Ten years later, Seth is still married. My wife divorced me when she decided she liked pussy more than dick. For a few years I dated a variety of women. Even though Carrie left me for another woman, I still carried a torch for her. No woman could please me.
Rewind back a few years and not long after Carrie left me. I went to a bar one night by myself to drink away my depression. As I pretended to watch whatever was on the television above the bar, I drank one beer after another.
At some point a woman sat down next to me and struck up a conversation. It was obvious she was on the prowl. I hadn't had sex since Carrie left me and to be honest, I didn't want to. Alcohol never leads to good decisions, and it didn't that night either. When I began to flirt back, she became bolder. Her hands started touching me, first my arm, then my back, soon my thigh, and her fingers even brushed across the erection hiding in my pants.
When she got up to go to the bathroom, the bartender, who was a woman, came over to me and said "You better be careful with that one. You might get more than you bargain for." She winked at me and giggled. I was too drunk to try to make sense out of what she meant and really didn't care. Between my depression and the alcohol, I was just looking to get my rocks off.
After the next round of drinks were drained, my new friend Carley asked if I wanted to go back to her place for another drink. When I agreed, we both stood up to leave. I was getting cash from my wallet to pay the tab when the bartender came over to me with a big smile. "Good luck. Let me know how it goes, okay?"
"Uh, yeah, sure. Next time."
"Next time." she smiled and again winked at me.
Carley lived walking distance from the bar. Since I was in no shape to drive, we walked less than five minutes to her place. Once we were inside, she closed and locked the door before turning to me. Suddenly, her eyes were filled with lust. Wrapping her arms around me, she began passionately kissing me. Her hands roamed over my body.
Breaking our kiss, she pulled me by the hand to her bedroom. She took total charge. She undressed me as she resumed kissing me. My shirt was quickly pulled over my head and thrown across the room. I kicked off my shoes as she unbuttoned my shorts which easily fell down around my ankles. Breaking our kiss, she dropped to her knees, tugged my underwear down, and took my hard cock into her hands.
"Beautiful." She said as she studied it. Looking up, our eyes met. Smiling she opened her mouth. Her head bobbed up and down on my cock aggressively. In short order, I felt my orgasm building.
"If you don't stop, I'm going to cum." She didn't stop. Instead, she moaned encouragement. "Carley! I'm gonna cum."
As my cock exploded, she renewed her moans of approval. Her lips tightened around my cock to prevent anything from escaping. As my orgasm subsided she continued to gently suck and lick until I couldn't take any more.
"Did you like that?" She asked smiling.
"Is that a serious question?"
"I just like to hear it. Tell me you loved it."
"Without exaggerating, I can honestly say that was the best I ever had."
"Really. You don't have to say that just because I made you cum."
"No, I'm serious. You seemed to enjoy yourself. That makes it even more exciting. When you aren't just doing it because you think you have to... not that I've ever made anybody do that."
"I know what you mean. And yeah, I love sucking cock. Does that make me bad?"
"Not in my book."
She leaned in to kiss me. When I didn't try to avoid her kiss, she seemed to get even more excited. Her tongue aggressively explored my mouth. I could taste a hint of cum on her lips and tongue. It wasn't a turnoff, which surprised me. When she broke our kiss, she stared into my eyes. After a brief pause, she smiled.
"Do you always do that?" Carley asked.
"What?" I asked even though I knew what she meant.
"Do you kiss your lovers after they blow you?"
"Uh... no. I haven't done that before."
"Why did you do it now?"
"Because you wanted to kiss me. I didn't think it would be polite to refuse a kiss after what you just did for me."
"Wow. Lucky me. So, does that mean you'd have done anything I wanted?"
"I don't know. Maybe."
"Well, Damn! I wasted my trump card."
"Maybe... Maybe not." I responded with my own smile. I began to undress her. She didn't resist. Instead, she stood very still, letting me remove her top and then I expertly, and with one hand, undid her bra.
"Impressive." She said with some admiration as she dropped her arms and slightly hunched her shoulders. Her bra dropped to the floor, revealing her C cup breasts and pink nipples. When my hands instinctively reached out to touch them, I could tell she had implants. I didn't care; they looked great. I enjoyed caressing her and lightly pinching her hard nipples.
I bent down so I could suck on her nipples. Her moans grew louder. I interpreted her moans as approval for me to go further. My hands started working on removing her shorts. Her hands pushed down her shorts and panties. I was still focused on her breasts when she turned away from me. Looking over her shoulder, she gave me that come hither look as she crawled onto her bed. I admired her ass as I followed her lead, joining her on the bed.
"Like what you see?"
"Oh yes! You're gorgeous." I grabbed her ass and squeezed.
"Before we do anything else, I need to tell you something. Please don't get mad, okay?"
"I'm not someone who gets upset very easily when I'm naked." I laughed nervously.
"I hope so." Carley then rolled over while slightly spreading her legs. My eyes locked at the sight between her legs. She had a cock that was a good two inches bigger than my six and a half inches. "Don't be mad, please."
I had never been this close to an erect cock other than my own. An odd feeling came over me. I wasn't repulsed by it. Carley was a pretty woman even if she wasn't a "real" woman. I honestly had no idea she was trans. Now the words of the bartender made more sense to me.
"Jim?"
I had been staring at her cock. To be sure, it was a bit of a shock to see what was between her legs. I should have jumped up, put my clothes on, and ran out of there. But I didn't. My eyes moved from her erection to look into her eyes.
"Can I touch it?" I asked softly.
"Yes." She whispered with obvious relief.
When my hand encircled it, I felt my cock start to grow harder. Touching her cock was like nothing I had ever felt. Surprisingly, it didn't feel anything like touching my own. I explored her shaft and balls. She was completely hairless, making her cock look even bigger than it was. Her balls hung down, heavy with the promise of a huge load of cum. When Carley saw me lick my lips, she spoke words that I wasn't sure was an invitation or a command.
"Go ahead. I can tell you want to." When I looked into her eyes again, she had a twinkle in them and also a sexy grin on her lips. "Make me cum, Tim. It's okay. I won't tell anyone."
Her words put me in a trancelike state. My only response was lowering my head and letting her cock slip between my lips.
"Oh, yes Timmy. Your mouth feels so good on my big clit. Suck me."
It was surreal. Not just that I had a cock in my mouth but that I did it willingly. Even worse for a lifelong heterosexual, I was enjoying it. Bobbing up and down on her "clit" was fun and exciting. I was almost completely erect again after just blowing my load a few short minutes ago. Using my mouth and hands, I had as my goal to make her cum as quickly as possible. I knew what I liked and mimicked some of the things she had done to me thinking she might like having her cock sucked that way. I'm not sure who was surprised more, Carley or me, but her orgasm came on quickly.
"Oh damn! You're good. I'm gonna cum. Suck it down Timmy. Swallow it all if you can." I'm not sure I would have had a choice in the matter. When her cock shot the first stream of cum into my mouth, she had grabbed my head to make sure I didn't pull away. "Swallow it! Oh, fuck! You are so sexy. Swallow it."
I don't know how many times her cock contracted and sent streams of cum in my mouth. I know I couldn't keep up with it though. Cum dribbled out of my mouth and down my chin, onto my neck. I swallowed several times as I attempted to "swallow as much as you can."
When she finished, she gently pushed my head away. We stared at each other until I asked, "Did you enjoy that?"
"Oh my god. I haven't cum that hard in a while. You did great." Studying my face she asked, "That wasn't the first time you've sucked a cock, is it?"
"Yes. I mean, I've never done that before."
"You have missed your calling then." She giggled.
"I don't know about that. I don't think I would suck just anybody. I wouldn't suck another guy anyway."
"That is the sweetest thing you could have said to me! You really don't see me as a guy do you?"
"No... I mean. I know you have a... a penis..."
