Scott's Shemale Surprise

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After Scott's divorce, he encounters a shemale.
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Scott looked at the papers in his hands and felt a sense of finality. The divorce was final. They both had wanted it, but it was still bittersweet. He felt like he should at least "celebrate" with a beer or two. There was a bar two blocks up the road from his apartment, so yeah, why not? Scott got dressed and headed down the three flights of stairs to the lobby and out the door.

Scott walked in, sat at the bar and ordered a beer. He sipped on it really while he watched some sports highlights on the tv mounted on the wall. This wasn't really his thing and he knew it. He quickly downed the rest of the glass and was going to leave when a beautiful woman sat at the bar two seats away from him. She looked to be about 5' 10", long reddish brown hair that stopped around mid back, maybe 140 ponds and wore a tight fitting red dress that accentuated every curve on her body, especially what looked to be some solid C cup tits, maybe even D cups. Scott didn't even realize he was literally staring at her when she took her first sip of her drink and said "Store bought."

"Excuse me?" Scott asked as he broke his stare from her body and finally looked at her face.

"My tits. They're not real. D cups and purchased. So...store bought."

"I'm sorry. I really didn't mean to stare. I was just stunned at how sexy you looked. It was horrible of me to be gawking at your tits like that. Please forgive me. My name's Scott." He reached his hand out for a shake after introducing himself.

She daintily shook his hand and said, "Nice to meet you. I'm Terri."

"Nice to meet you too. I was about to leave, but I'll stick around fir another round if you'd let me buy you a drink."

"Look," Terri said. "It's nice of you to offer, but I'm not really looking for anything right now. I just got out of a horrible relationship and I just wanted to have a drink and be by myself."

"Fair enough. I just had my divorce finalized and wanted the same. Really. No hitting on you. Just some drinks and some conversation. Come on. What do you say?"

Terri didn't say anything, but smiled and patted the seat next to her. Scott hopped up on the seat and ordered them both another round. The night went on like this, round after round, with nothing but small talk between them. What they did for work. Where they were from. Music they liked. Shows they've seen. Next thing they knew, it was last call and they were both pretty drunk.

Scott stood up and said, "Well Terri, I enjoyed getting to know you, but I'm gonna go home, jack off and the pass out."

The bluntness of his statement made Terri bust out laughing. "Nice visual." she said.

"You're welcome to come watch. I only live a couple blocks away."

"How can a girl turn down THAT offer?"

Scott stumbled out the door and made his way back to his apartment building as Terri followed close by. She laughed and giggled the whole way "There's no way he would just whip his cock out and just start jacking off" she toughs to herself. Terri followed Scott up to his apartment and in stunned silence, watched as Scott did just that! He took off his pants and underwear and started stroking his cock! It was 3/4 erect and a modest 6". Terri guessed it would gain another inch to put him at 7" if he got it fully hard.

It was Terri's turn to be caught staring this time and she sat on the couch and laughed when Scott caught her. He wasn't ashamed of it, he was just horny and since he had promised Terri he wouldn't hit on her, he was going to take care of his own problem. "You want a beer?" Scott asked as he walked into his kitchen, hand still stroking away.

"Uh....ummm, sure," Terri said

Scott grabbed a beer from the fridge and made his way to the couch and sat next to Terri. He handed her the beer. Terri took a sip then asked, "None for you?"

"I wanted to take care of myself first. Then I figured I'd join you."

"Ahhh. Looks like you're having a bit of trouble there."

"Too much to drink. Its not getting fully hard. You want to help?"

"Thanks for the offer, but my arm is kind of tired," Terri said, then laughed.

"No not like that," said Scott. "I mean like a kiss. Kissing is a big turn on for me. We kiss, I get hard, I take care of myself. Then we can just drink and talk some more."

"Look....Scott. I am enjoying being around you. I really am. But there's something you don't know about me. And if you knew, you definitely wouldn't want to kiss me."

"You're a lesbian?"

"No."

"You're not a lesbian. But kissing me would be bad?"

Terri stood and started to pace around while she talked. "No. Kissing you would probably be great. In fact blowing you would probably be great. You have a pretty decent package. It's this thing. Something you should know. FUCK!"

"So tell me then," Scott said.

"It's probably better to show you. I just get nervous about these things," Terri said. But with that, she walked over to where Scott sat. His face was at waist level, which was good for what Terri was about to do. She exhaled nervously and pulled her dress up. The dress was tight enough that it wasn't going to just fall down again. Her lacey panties were now exposed. Scott's eyes took it all in and he breathed harder. He got turned on quickly at the sight of Terri's panties. But Terri wasn't done. She pulled the panties down slowly and from them spilled out a hanging, soft 7" girl cock, thick and circumcised. Scott's eyes widened in disbelief!

"I'm straight," was all he could muster up to mumble, but yet he couldn't take his eyes off of her cock.

"I believe you," Terri muttered. She noticed though that Scott continued to stare. "Scott? Scott?". No response came. She saw his eyes were transfixed on her girl cock. She swayed her hips which caused her cock to swing back and forth. His eyes followed along. Then she noticed his dick stood at full attention. Terri thought to herself, "He may be straight, but he likes it. Can't take his eyes off it."

Now emboldened, Terri took a step closer and gently cupped the back of Scott's head in one hand while her other hand grabbed her cock and positioned it in front of Scott's mouth. His mouth opened wide so Terri pushed the tip inside it. The pleasure sensation is immediate and Terri's girl cock responds. Scott responded also by moving his head front and back, front and back, and he effortlessly became a cock sucker.

"Oh fuck," Terri moaned. "It's so good to be in someone's mouth again."

Scott pulled his head back and let her cock pop out of his mouth. It was so fucking hard....and HUGE! "You are fucking hung Terri," said Scott.

"Little under ten inches when I'm hard."

Scott stood up and embraced her. They kissed animalisticly. Scott fumbled with his hands behind Terri, desperately trying to unzip her. Together they got her dress off. Scott licked each tit before Terri pushed down on his head, bringing him to his knees in front of her cock. He simply states again, "I'm straight," before he gobbled half of her cock into his mouth.

"Says the guy sucking my girl cock!"

Terri started to push her cock forward in rhythm, in and out of Scott's mouth. She fucked his mouth for a while and it seemed to urge Scott on. He started to get more and more of it in with each thrust. Terri closed her eyes and relaxed. The sensation of getting a blow job excited her. "Just like that baby. Suck my cock. You're so fucking good at it. I'm close to cumming. You want my cum, don't you.". Only a nod of his head which felt different against her cock. Terri grabbed Scott's head with both hands, slowed her pace to full inward thrusts, grunted. A grunt then a slam of her cock down his throat. Pulled out then another grunt and a slam of her cock down his throat again. Five thrusts like that and she breathed heavy and grunted one last time as she slammed her cock down his throat one last time and held it there. "FUCK I'M CUMMING!"

A warm sensation spread through Scott's mouth. He realized Terri was cumming. It was salty, but tasted like heaven. He felt her cock head grow each time she sent a spurt of cum into his mouth. He swallowed it all, actually found himself savoring the flavor as each spurt built up against his tongue before he then swallowed it.

"For a straight guy, you sure give one hell of a blow job," Terri said and winked at Scott. She also looked down at his cock and laughed. "Looks like your problem is taken care of."

Scott looked down and saw that not only was his cock soft, but he had cum all over the floor. He looked up at Terri embarrassed. "I was so busy, I didn't even feel myself cum! Damn, sorry I won't be able to return the favor."

"That's ok. I'm not done anyway."

"You can go again that quickly?" Scott looked at Terri's cock and was shocked to see that it was still hard. Maybe shrunk by a half inch or so, but still at the ready.

"I'm usually good for two or three rounds," she said. "Get some lube and get on all fours."

"I don't think. I mean I couldn't. I can't take that monster. If you wait around a bit, I'll get hard again and I can fuck you."

"I don't bottom baby. I'm strictly a top. I understand if you can't though. We can always be blow or jack buddies."

Scott approached Terri and kissed her deep. Their bodies pressed together and he felt her tits against him. Her cock pressed against his body as well and he found he was turned on by this. He broke the kiss and led her by the hand into his bedroom. He kept some lube on hand for those nights his bare hand wasn't enough. Scott tried to hand her the bottle, but Terri shook her head and pointed to her girl cock. "You put it on baby. Your hand on my cock is gonna feel so nice."

Scott got down on his knees again and on an impulse, took a long lick of her cock, from the base to the tip, before he then squirted a generous amount of lube onto her cock. He then used both hands to rub and tug on Terri's cock to spread the lube. He could feel the hardness and texture of her cock. It felt very powerful. He got up and handed her the bottle, then got into position on the bed, on all fours.

Terri positioned herself behind Scott and squirted some lube between his ass cheeks. She rubbed it up and down his crack and made sure to get his asshole plenty. "Spread your cheeks baby," Terri said. Scott reached back and did as he was told. Terri gripped her cock and placed the head firmly against his sphincter. She pushed forward slowly and felt Scott's asshole give way. The head of her girl cock slipped inside and she immediately felt the warmth and tightness of Scott's ass.

"Uuuunnnnffffff," was all Scott could manage to say.

"Try to relax baby. I'll be going slow at first and you'll loosen up. As tight as your ass is, I probably won't last long anyways." Terri pushed a little harder and got another inch inside. She pulled back until just the head of her cock was about to slip out, then pushed forward again a little harder. She guessed she was about four inches in now. "Perfect," she thought. Terri started a rhythm now, out then in, each time she made sure the tip of her cock stayed inside, then in again only the four inches. She actually felt the moment Scott's asshole relaxed and loosened up. It was followed by an exclamation from Scott.

"OH FUCK!" Scott yelled. "Your cock....your cock feels....fucking amazing!"

"That's it baby. You're my cock whore now, aren't you? Your ass likes it so much it's opening up for me to go further."

Terri picked up the pace and the distance she pushed inside. A medium pace ensued as two more inches penetrated Scott. She knew he was new at this, so she kept that pace, she didn't want to push it. Terri reached underneath Scott as she wanted to help his cock to get hard. She was not altogether surprised to feel he was rock hard and leaked pre cum like a sieve.

Scott said, "My cock feels weird. Like I'm pissing."

"Would you like to see why Scott?" Terri asked

"Yyyyeeessss."

Terri knew she would have to be quick. She slowed her pace, pulled her cock from Scott's asshole and in one smooth motion rolled him over onto his back, grabbed both his legs and lifted then, without needing to guide it, slammed her cock back into Scott's ass. Every inch this time, her balls slapped Scott's ass cheeks when she was in. He howled in both pain and pleasure. Terri started a more rapid and deeper pace as she needed to cum now.

"Look at your cock Scott." said Terri.

Scott did, and saw that with each deep thrust his cock was leaking pre cum. And pre cum might not be right because he felt it getting rigid. His balls tightened. "FUCK," he screamed. His cock exploded hard enough that the first spurt of cum actually landed on his face. When his spasm ended, he had came all over his face, chest and abs.

Terri was spurred on by this. Her thrusts became harder. "Fuck baby, that's hot!" she said. "But watch this." She pulled her girl cock out of Scott's asshole and aimed just in time to spray several ropes of cum all over his chest. Two smaller shots hit his abs, and one final sputter dripped the last of her cum onto Scott's cock.

Terri fell, exhausted, onto Scott. Their bodies slid against each other and mixed the cum together. She still willed herself to get on her knees, leaned over and licked up strands of cum into her mouth. With enough built up, she had a target in mind. Terri slid upwards and kissed Scott, felt his mouth opening. Scott accepted in her cum kiss, both of their tongues danced with each other's and shared the taste of each of their cum.

After they rested for a while, Terri had to sadly call it a night. Still sloppy with cum all over her, she dressed and kissed Scott one last time before she left. But not before they exchanged numbers. She stood in the elevator on the way down and thought "This could be a good regular thing. So many other things she wanted to do to that ass!"

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17 Comments
ColonelRebColonelReb4 months ago

What a fantastic story. I had my cock in hand stroking myself and wishing I could find myself in that same situation. Oh how fun that would be.

RodimusMikeRodimusMike11 months ago
I'm straight.

When Scott replied I'm straight was like the coolest thing,and yet he proceeds to have sex with Terri. Now it is often that Men Shemale Chasers don't consider themselves gay for being attracted to Shemales or even being with them.

For all intents-and-purposes Shemales or Trans Women only see themselves as Women with something extra down there.As for pussies in all honesty are so overated and sure some Men like pussies on women but pussies in general are not really a necessity especially considering the implications of having sex with one,possible pregnancy and lifelong responsibility.

No its not really a coin toss but when faced with possible pregnancy or being with a Shemale the choice seems almost like a no-brainer.On the other hand you do have to face the fact that some TG's are strictly Top Doms and your at risk of becoming a full bottom and only getting plowed.Granted there are also Non-Dom TG's who are perfectly contented to being bottoms.Just depends on how you look at it.

In closing I myself love TG's but I am not strictly top or bottom,but versatile and yes I am a Man but consider myself also straight because when I see TG's I only see Women with an extra attribute,along with her tits.

AnonymousAnonymousabout 1 year ago

Great story! Would love to be in Scotts situation have thought about it a long time just never Acted on it.

AnonymousAnonymousabout 1 year ago

You certainly do have a very kinky, and interesting, mind. Thanks!

Client8Client8almost 2 years ago

Luv them bottom boy stories. Acouple typos but so what. Part on, Garth!

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