The Big Mature Shemale Next Door

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SugarandSalt
SugarandSalt
4,417 Followers

One night Warren was in her bed. He was naked except for a pair of briefs. Barbara was completely naked. She laid on her side next to him, running her hand along his back and letting her erection rest across his bottom. She was just finishing up a story about the time she fucked a door-to-door salesman who couldn't stop staring at her tits long enough to try to sell her on his product. She had wanted the thing that didn't cost a thing from him, his tender, vulnerable asshole. And she took it.

"Why don't you sleep in here with me tonight?" she asked Warren as though she'd just thought of it.

"Yeah," he told her. Warren stretched out on her bed, clearly enjoying the way she rubbed his back.

Barbara leaned in closer to him and blew hot air on his ear. She started to nibble at his earlobe. Barbara whispered, "What would you say if I told you I want to stuff your little ass with my cock?"

Warren turned toward her and Barbara kissed him full on the lips for the first time. Their tongues tangled together as her erection squeezed between their stomachs. "I'd ask if it hurts," he replied.

She licked at his neck and responded, "Mmhmmm... for a while. It feels good too. I was afraid my first time. He was a lot smaller than me too. I'd understand if you didn't want to. But I have to say, I think you'd like it, dear."

"Do it," he whispered.

Barbara didn't say anything. She looked into his eyes and then sat up on the bed. Barbara spread her palms over his ass cheeks. She flipped her fingers into the waistband of his briefs and pulled them down his legs and off. Barbara licked her fingers and pressed it between his cheeks. She covered his little hole with spit. She stroked her cock until it was leaking precum. Warren winced when he felt the warm liquid drop onto his opening. She spread one cheek from the other in her strong hand and pressed a finger into his entrance. His sphincter contracted hard around her finger. She pushed in deep and then slowly drew in and out of his vulnerable wrinkle.

She calmly withdrew her finger and told him, "It's gonna be my cock next. Don't panic." Barbara worked up more precum and coated her shaft with it. She slid past his cheeks and let the head sit at his entrance. "The first few inches are going in fast so it won't hurt as bad for long. It's ok, darling."

Warren felt the tip press into him and then in a flash Barbara thrust her cock through his defenseless sphincter. Warren cried out, clutching at the pillow under him. He felt like she'd split him in two. Barbara pressed her body down on his. Her tits squashed against his back and she whispered, "That might just have been the worst of it. I'll go slow. Oh fuck, you're tight." Barbara moaned into his ear. "I'll go slow..." she repeated again. The feeling was unlike any Warren had ever experienced. His tender insides clutched her pole with everything he had. Barbara was steady, slowly skewering him an inch at a time.

Warren groaned. Finally he felt their bodies meet. Barbara's balls rested against his. She told him, "Get used to it. Your ass is so wonderful, darling. We shouldn't have waited so long to do this." Barbara flexed her womanhood inside him. "Don't think about the pain. Listen to my voice. I know how much it hurts at first. I've had plenty of big rods jammed up my rear end." He gripped her pole even tighter. Barbara grabbed her tits and rolled them around the back of his head. She squeezed his head between them to occupy him while the pain passed. Warren whimpered, mumbling that it was ok to keep going.

Barbara took much care in withdrawing her cock. The inches slipped from his asshole. She pulled out until only the head was left inside him. She humped him gently. The urges she'd developed as a young sexually active t-girl years ago were to impale him and fuck his guts out. She tried to resist them. His muscles squeezed her shaft as she pressed in. The friction her length encountered on the way back in were like fireworks of pleasure for her all going off at once.

She started a string of thrusts into him. Warren's pain started to dull, he had this feeling of alleviation. The pain he felt became something else. It was steadily turning into a new kind of pleasure. Barbara started to fuck him a little harder. She relished deflowering his sweet bottom. Barbara always loved the power it gave her. Having her penis buried inside a man meant they were at her mercy. Barbara groped his young body, digging her entire length into him.

"It isn't so bad, is it? You're doing such a good job, dear. I'm gonna go harder now." Barbara, her cock still buried inside, pulled herself off his body and lifted him by his hips. She started to give it to him doggy style. Barbara's hips jabbed into him. Warren grunted. "Mmmm.... baby... darling... you're taking it so much better than I thought you would." Barbara's thrusts were so deliberate, she was taming and teaching his asshole how to be a good, dutiful fuckhole. "You're as tight as I've ever had. You feel so good... so slippery and tight. I love it." Barbara threw her weight behind a deep stroke and moaned, "Fucking love it!"

"Take me," Warren whispered at first. Barbara pounded him harder. "Take me." he said again. "Fuck me!" His ass took every thick, experienced inch.

Barbara drove her length into him. Her balls slapped against his. She crushed him into the bed and hammered his hole like she hadn't fucked in ages. Warren, for his part, humped his little ass back at her. His butt felt like it was on fire and he needed more. Barbara's thrusts became increasingly desperate. She screamed, "Oh FUCK! I'm gonna cum. I'm gonna fill your ass so deep!"

Warren's muscles clamped down even harder around her girth. He was sweating and so was she. He voiced his pleasure in groans. Barbara buried herself inside him and let out a loud, primal cry of pleasure. Warren grasped the sheets, moaning. He felt his own hard cock start to spew against the bed. Barbara's cock pulsed; her cock hit a spot so deep inside him and then she exploded. Barbara came and came. Warren was completely filled with her love goo.

She collapsed on top of him, her cock continued to spit strands of ejaculate which coated his insides. "That was so damn good. I got you and filled you good," she panted. Barbara had a satisfied smile on her lips. She reached around Warren, who was just recovering from his orgasm, and found the sheet under him covered in cum. She gave his cock a stroke, "You shot your load, too. Mmm..."

Barbara laid on top of him afterward. She kissed and whispered things to him. It was minutes before she finally got off of him and said she'd be right back. Warren turned around on the bed. His ass was sore, but in a lot of ways, it was a pleasant soreness. Barbara was grinning ear to ear when she returned to the bedroom. Warren watched her cock swing between her legs. She had a camera in her hands.

"What's that for?" he asked.

Barbara snapped a photo of him. Then another. "I know you won't be around here forever. You came and that's all the proof I need to know this is the life you're gonna have." Warren's face turned red as he considered the truth to it. "You're going to find a girl your own age who does what I just did. I want things to remember you by." Barbara snapped another photo of him.

He was a little embarrassed at first that she was taking pictures of him with cum dripping from his ass, but then he realized that was exactly what she wanted. Warren started to get more into it. He posed for the camera. Her cock was growing. He wrapped his hands around the shaft and put it up to his face *snap*. He rubbed his cheek along it *snap*. Warren kissed the tip *snap*. He turned around and spread his sticky cheeks *snap*.

***

Warren woke up the next morning in her bed. He could smell breakfast cooking. Warren slid off the bed. A dull ache reminding him of their activities last night. He smiled to himself. Warren groggily walked into the kitchen.

"Good news," Barbara told him warmly. She was flipping pancakes.

"Hmm?"

"My niece is going to spend the rest of the summer with us." Barbara sounded almost giddy. "I told her about you staying with me. Even sent her one of those photos I took of you. I can't wait til you see her cock. She really reminds me of myself when I was younger. We're gonna have so much fun together." Barbara flashed him a big grin.

There were two of them? There were going to be two of them under one roof with him? Warren's legs went weak.

SugarandSalt
SugarandSalt
4,417 Followers
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173 Comments
smoothwienersmoothwiener25 days ago

This was so hot to read..

DrDrk_4955DrDrk_4955about 2 months ago

Very, very interesting!!! Only an experienced and mature (person) knows how to be gentle and patient with an inexperienced partner.

A well told story and a follow up chapter or more would be GREATLY APPRECIATED!!!!!! The tales the three of them could tell!!!!!!!

Thank you!!

AnonymousAnonymousabout 2 months ago

Would love the next part of story when the boy does it to shemale’s ass Their assholes are so accomodating and experienced!

WoodwiseWoodwise3 months ago

2 of them,, lucky lil boi

bulldog0826bulldog08265 months ago

Would love a continuation of this story!

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