Bend Over Boyfriend

Story Info
The first time she gets to use a strap-on isn't on a girl.
1.8k words
4.36
85.1k
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Alice couldn't contain her excitement. She was half an hour away from seeing her boyfriend Bob and her head was filled with memories of last night and intense anticipation of the near future.

She pretended to be working on her assignment, tapping the key in a regular rhythm as she actually recalled the previous night on webcam.

It had started innocently enough. Just a visual link so they could see each other's expressions and gaze lovingly into each other's eyes as they chatted via text. The sexual tension had built and he'd asked her to give him a show. It was freezing in her house. She'd got as far as unclipping her bra when she'd shivered uncontrollably and abandoned the act. Unsatisfied, he'd begun stripping for her in the comfort of his heated room.

Then he'd showed her his dildo.

It was thick and dark and incredibly intimidating.

You are not using that on me, I'd break in two! she typed quickly.

It's not for you, it's for me. He replied.

Her jaw dropped open. You... do that?

Yes. He nodded vigorously as he typed.

I wanna watch.

He smiled, pretending to act shy as he lubed up his toy. Taking the keyboard with him he lay down on the bed and prepared himself.

She watched, mesmerized, as he slowly inserted the toy.

When it was in all the way to the hilt he stopped. And that's how a man takes it.

I could learn a thing or two from you. She replied, not looking down at the keyboard once.

He grinned and flicked a switch on the bottom of the toy.

Setting 1. He typed. His face relaxed as he pushed the toy a little deeper.

Alice clenched her legs.

Setting 2.

He shifted, rolling his body slightly with each movement of his hands. His lips pursed and opened as the toy slid out and was pushed back in again.

She licked her lips.

Setting 3.

His brow furrowed and he threw his head back, mouth open and chest heaving.

Unable to contain herself she slid a hand into her pants and started touching herself. Each time he pressed the toy back in she pressed her fingers into her slick inner walls. She nearly came as he reached down and started pumping himself. His face contorted with pleasure s he bucked his hips into his right hand. Alice threw her other hand under her waistband and rubbed her clit furiously. She could feel the wave of ecstasy pounding at the gates, demanding to be let out.

His body froze up and with a shudder he came. Spurts of translucent liquid splattered across his stomach as he soundlessly cried out.

Alice convulsed, her eyes shutting against her will as she came over her own fingers. Her inner walls tightened, trapping them almost painfully before releasing them to a cascade of fluid. She left her hand there, enjoying the wet feeling and allowing herself for a moment to imagine it was another girl's insides. She bit her lip and trembled as that transformed into his hot insides, slick with lube.

Jacob's voice smashed through her memory, jarringly loud. "That it, I give up. Hometime."

She stared blankly at her computer screen. It was five o'clock. Five o'clock!

She threw her belongings into her overflowing bag and raced out the door. It was time! Tonight her fantasy was going to come true!

They had a leisurely dinner and even dessert before she popped the question.

"Can I!?" she said a bit too exuberantly. He laughed.

"No, no, this was all just a practical joke. I'm actually gay and about to break up with you." he teased.

"Well we had a good run."

"You're lucky I'm secure in my masculinity. Unlike some people."

"Hey, I'm just waiting for my nads to drop down and I'll be secure in mine too."

He grinned and tickled her, eliciting a girly squeal. "And lose that soprano? No no, I'm afraid it's the eunuch life for you."

"Well darn." She kissed his cheek. "Guess I'll never be a real boy then."

Giggling they headed back to his place.

"So how do we..." she began to ask but he put a finger on his lips. "Stop thinking." He kissed her slowly. "Feel it."

She grabbed his butt. He squeaked.

"Like that?" she grinned.

He growled and pushed her down onto the couch. They kissed passionately and he started nipping his way down her neck.

"I thought I was supposed to-" she gasped and shut up when he put another finger to her lips. She licked it.

He gripped her waist tightly pulled her dress over her head in once swift move. Settling between her legs he continued to bite his way down to her stomach. She gave up on the idea of control and let her head roll back as she enjoyed his hot wet mouth on her chilled flesh. His hands stroked her thighs while keeping them firmly apart. Somewhere between the mouth and the hands she lost her underwear, leaving her exposed.

His tongue darted across her lower lips, his hot breath making her fingers twitch. Slowly, gently, he licked the length of her, taking care to flick the tip of her clit at the top each time. She trembled, her legs trying to clench as the tension built inside her. His strong hands kept her legs firmly apart though.

Just when she thought she was going to have to grab his head as encouragement he changed tactics. He circled her clit with his tongue, unwinding her slightly with each cycle. She exhaled gratefully and gasped when his tongue suddenly delved inside her. It thrust again and again, practically vibrating and tossing her over the edge of ecstasy. She arched into him and collapsed gratefully.

He pulled away and she was seized by the urge to follow. She grabbed his hips and pushed him down onto the nearby pouf, engulfing him with her mouth. He cried out as she sucked away at him, suddenly desperate to make him come like he had made her.

After minutes of thrusting her mouth down onto his shaft he pushed her away. "We were going to do something else tonight." He panted.

"Oh right!" she chirruped happily and ran to find her overstuffed bag. She returned with her favourite toy, a double-ended dildo she'd purchased in hopes of finding a girl who would let her use it on her. Instead it would be christened by a man.

She tugged her boyfriend about until she settled on laying him stomach-first over the pouf. From there she kissed and ran her nails lightly over his back, much to his enjoyment. When she felt comfortable enough she unscrewed the lube and added a small amount to her fingers. Running her tongue along his back she circled his ring with her index, slicking it up. His body remained relaxed.

She applied some more lube to her fingers and while stroking his hip with her free hand she slid it a little way inside. It felt different to her body. Colder. She attributed it to the lube.

After a few moments of feeling her way around near the entrance she began scissoring her fingers to stretch him. He mewled appreciatively. When he felt relaxed enough she withdrew and pulled out her second favourite toy. It was the first dildo that had ever made it inside her back entrance and now it was going to be a first again.

Coating it with lube until she could bare holding it she placed it at his entrance and switched on the vibration. Holding there she stood up until she could lie across his back and nip at his ear. Slowly, she pushed it inside. It went in shockingly easily.

"You've done this a lot, haven't you?" she whispered in his ear.

"Mine is just a lot bigger than yours." He breathed.

Less worried that she would hurt him, she pressed it all the way inside and began thrusting slowly. His back arched beneath her and his breathing hitched. In minutes he was whimpering and thrusting back for more.

She could feel herself growing wetter with each sound and thrust. Finally she couldn't take it anymore. Being careful to slide the toy out slowly she placed it to the side and tugged on her strap on.

He keened for her to return.

One end slid in her easily, making her hiss as she realized how large it was. She rubbed an excess of lube onto the exposed end and positioned herself at his entrance, trying to find a comfortable footing.

The end slid in without any effort, making her gasp as it pressed back against her cervix. She pushed onward until she was buried close to the hilt. Experimentally she pulled back out, feeling each ridge on the toy catch at his entrance. He didn't seem to be enjoying it much. She pressed back inside and when she reached the hilt she pressed a little more, biting her lip as the other end ground into her cervix.

He let out a moan and to her surprise pushed back.

She pulled back until there was no response from his body and pressed back in again as far as she could go. Sliding in and out onto a few centimeters she soon had him rocking his hips in time to her rhythm and moaning in a curiously high-pitched manner that made her weak at the knees.

After one particularly sharp gasp followed by groan she decided it would be even more fun to see his reaction. She slid out of him and tugged his shoulder. He rolled over with some difficulty. He looked up at her with glazed eyes.

Biting her lip she slid into him again and nearly came as his face contorted with pleasure. He keened, his erection devoid of any friction now. She slid out of him for a moment and engulfed it, licking her way up and down his shaft. He nearly yelled in surprise and pleasure. She stood up again and slid back inside him, gripping his hips and thrusting hard, confident that was what he needed. As she watched his head roll around and the muscles in his stomach tense she reached forward and stroked his wet cock. She was rewarded with a symphony of moans and grunts from his entire vocal range.

She didn't have the years of practice he did though and let him take over when he reached down to touch her hand. Thrusting into him furiously she watched in delight as he pumped himself dry, coming in great long spurts just as he had the night before on webcam. This time she could hear his orgasmic cries though, and it sent her tumbling over the edge. Together the pair came until they were weak but satisfied.

Carefully, trembling, she removed her toy from his limp body and struggled to remove it from her own tight orifice. Throwing it to one side she leant over the man she adored and kissed him passionately.

"Hey..." he murmured in her ear. "I love you."

"And I fucking love the way you moan, oh my god." She gushed.

He laughed breathlessly.

"So, at the risk of sounding like every insecure guy in existence; how did I do?"

"Just great." He kissed her forehead.

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3 Comments
FrankdockFrankdockover 1 year ago

Excellent storyline. Your bantering between characters was a nice touch. I liked it as a hot Fun story and very well written. 2 thumbs up.

jackbirdjayjackbirdjayalmost 10 years ago
wife dose me

Before my wife and I got married I brought toys in the bed. At first she was shocked but curious. Over the years she has used dildo's, vibrators, and strap-on's on me.

AnonymousAnonymousabout 10 years ago
Good short story

Many guys have secret desire for the dildo. Once a woman gets guy to take it relationship changes for the better.

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