First Time Guy Strap On

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Mike is just a normal guy and most girls would never know. He wondered about what it would be like to have a girl sexually use him like he had so many girls himself.

Mike was friends well friends with benefits with Jill. They hooked up from time to time when they were in between relationships. It was all in good fun they would both work out their sexual needs in random locations just to fulfill that weekly need of release. She was the submissive one and didn’t mind trying new sexual activities from time to time. They slowly graduated from sex all night to finally fulfilling one of Mike’s fantasies.

One afternoon Mike convinced Jill to try a bit of double penetration. First he had Jill lay down on her stomach and he worked his all day stiffening cock into her moist womanhood. After they had gotten things all nice and moist he insisted on trying one of her feminine toys on her anus. They were indeed successful with penetrating her butt and pussy at the same time. It was a slow and tedious process that yielded new sensations for both Mike and Jill. It was the tightest Mike had felt inside a woman in a long time. Further, it was most fulfilling for Jill during the stint of this adventure.

As fun as it is reminiscing about old times. They moved on over the years and eventually found new lovers. After a few years their lives crossed paths again for that need of sexual release after that hard day of work. Something to take the edge off that alcohol just won’t do.

Mike eventually through text explained to Jill that he always enjoyed dominating her in the fun of their countless sexual adventures. He explained that he would enjoy it if she would ever be interested in returning the favor of being the dominant one for the night. Mike was unsure of how to breach the subject of her being the one to be dominant enough to use a strap on in his never invaded hole.

Mike expressed again that he was curious about if she would have enough guts to possibly use her fingers near his butt. She replied that she had never explored a man’s butt and it definitely was a new idea to her. He then said he would even let her use her tongue on him. She immediately replied that she found that actual act a bit too disgusting. She replied again that she would consider using her fingers while giving him head on their next fun fest.

Thursday came and they met up at a hotel that they had been to numerous times and decided to have fun. Mike showed up first and hopped in the shower discarding his work clothes from the day. He lackadaisically admired his body in the mirror while letting the water warm up. He casually noticed that the time at the gym had been paying off and that he was actually starting to sharpen up. He noticed too that by the next time that he would have fun with whichever girl he was with he would need to shave himself. Mike jumped in the shower and washed himself of the days work. He even washed his cock and rubbed around his butt hoping the evenings festivities would bring about some fun.

When he got out he was met at the door by Jill who had just gotten off work as well. She showed up in a casual paralegal outfit complete with knee high dress a female sports coat half undone with a white button up revealing her tired looking breasts.

With the anticipation of rekindling an old flame they hurried themselves into meaningless kissing relighting an old flame of zero love and using each other for carnal instincts only. They groped each other in emek escort a frantic pace and led each other disrobing clothes along the way to the bed. Mike fell on top of her and started attacking her breasts pulling her bra down in anticipation. He knew it would be no time and her nipples with barbells through them would be hard. He shoved his hand forcefully into her panties and began massaging her whole sex into a fever pitch drip. They instinctively knew what they were doing, there was no time for the cutsie love escapades that their friends shared on social media. This was all about build up and release of sexual tension.

She responded by fondling his cock pulling and tugging on it with a firm grip. Even giving his balls a tug. She wanted and needed that release of an orgasm she trusted him to fuck her with out the use of a condom. Mike also trusted that she wouldn’t send him so far over the edge that he wouldn’t have time to get a condom and prepare his own orgasm in a bag. Mike knew she was ready when his knee felt the wetness in the bed that they had rented for the nights activities. He pulled away in the cool air and aligned his cock for her soaking entrance. He balanced on the sheets and slid in to a place he knew all too well. They began feverishly bucking and moaning it was more animistic than it was love making. He continued ramming his stiff rod in and out of her enjoying the feeling of her over wetness that he had missed. He hadn’t came in a while and he knew that it wouldn’t take long. He decided to end it early and see what else the night would bring. He pulled out and with the force of weeks worth of cum came all over the young gal who was granted her sexual release moments before with a face squinting orgasm.

They decided after cleaning up to go out for some dinner. Over dinner he egged her on about his desire to try for her to anally please him. He suggested that they could even visit the adult store and see if they would have any toys to help them through their conquest. They departed and headed to the adult store where and middle aged woman was happy to help them find what they were after. Mike explained that they were looking for a toy that would help him get over his desire for anal play. The attendant showed them around and even suggested that they try a strap on. Mikes eyes widened and went a bit pale with the thought of that. The attendant explained that lots of males have tried it and nearly all of them were disgusted by the thought of being with a male. Mike gave it some thought and asked Jill what she felt like trying. She simply suggested that she was up for anything and if it’s what he really wanted she would try it. They quickly found a starter kit that had a harness, some lube, and the object of desire. The dildo was a light blue in color almost easter pastel it was elongated to what appeared to be 7″ and was gradual in circumference. They payed for it and went on about their night. If they used it great if they didn’t he could always use it on her pussy or even her ass.

They circled back to the hotel ready for another session of sexual release no matter what was on the menu of desire. They quickly undressed and were on the sofa Mike’s hands vigorously working on her pelvic region and Jill’s hands automatically working over his hard cock. It was the biggest she’d been with and always wanted to return to it. In between breaths he suggested that she start the anal play. She in her submissiveness accepted eryaman escort the command and edged her middle finger down to his stiff feeling hole. It was puckered shut in anticipation of what may come. She felt natural in running her finger around the hole trying to open things up like she did the first time she felt like masturbating. Mike was aghast at the new feeling of not just his finger but a feminine finger exploring a lost sexual canal. He then leaned over her and suggested adding some lube to dull the tension in the air she complied by holding her hand out and taking some in her tiny hands. She moved the excess down to the bottom of his shaft and then rubbed it over his balls. Mike’s head momentarily flew back in the newness when he felt lube fall coldly and freely down his balls to his anal area. It reminded him of when a girls juices would slide from their sex down onto his nether regions while they rode him like a stallion.

Jill novicely worked her finger into his anal canal. She figured if she could finger herself well she could finger a mans hole. Mike obeyed by sliding down the couch to get more comfortable she felt more comfortable sliding in and out of his bottom just like her pussy would ache to have done at that moment. She kept working in and out of his tight hole. All the while Mike was enjoying this new sensation that he had never felt before. Mike grabbed Jill’s head and pleaded her open mouth down on to his stiffing cock. She engulfed him keeping her finger busy on his rectum. Mike was lost in excitement of receiving head and having his love canal explored at the same time.

He didn’t want to blow quite yet so be backed her head off of his head and moved her to a standing position. He then explained that he was ready for her to try on the new toy that he had purchased. He went over to the bag and tore the packaging open and removed it’s contents. Jill’s expression turned to uncertainty as she had always been so confident about just being a fuck for him. He encouraged her that she would be excellent at it and to not worry about how good or bad she would be doing at it. After all it was his First Time as well and he truthfully didn’t know what to expect either.

Mike quickly assembled the toy and encouraged her to try it on by kissing up her legs and her belly. All the while easing her legs into the straps. He finished by securing it up and around her waist. Jill was unsure of this new sensation that was around her waist. It felt like a pair of sleep boxers with a banana attached to the front. Once in place she felt a new wave of attention come over her she had the power of a woman’s sex and the power of a man’s all in one. By surprise she grabbed Mike’s head out of no where and pulled it to her new toy. Mike resisted.

“I’m not about to do that.”

“Shut up and just try it, you were the one that’s into this anyways.”

Mike went with the new avenue and slid his tongue out of his mouth closed his eyes as if giving a first kiss and closed his lips around the stiff shaft protruding in front of him. He sank down on it pretending he was a stupid young slut blowing a guy for the first time. He eased his head up and down pretending to fulfill the role. As his mind reeled he lost track of time going to town on this new toy that he never had the guts to try before. He excelled at sucking away at the hard plastic member. Jill became bored since she wasn’t receiving any real stimulation. She voiced up.

“Is esat escort that all your gonna do is suck this plastic cock or were you interested in going farther?”

Mike swallowed hard it was now or never no turning back. He voiced to himself fuck it you only live once might as well try it. He got up and decided to bend over the couch. Jill admired the ass before him.

“So this is what it’s like to see an ass up in the air awaiting some attention. No wonder you get so worked up when I’m on all fours. Maybe I will enjoy getting to fuck you like you do me after all.”

“Yea yea if your gonna do it buck up be a man and try it. Or I’m gonna back out.”

With that Jill rared down and slapped Mike’s ass with a crack.

“Just shut up, I’m in charge now. You put me in this position now take it like a bitch.”

Mike wondered what he had gotten himself into he rared up and started backing out. Jill had turned now though and wasn’t ready for some whinny bitch. She reached in here duffel bag that had handcuffs that he had restrained her countless times with and quickly restrained his hands behind his back.

“Your not going anywhere! You came this far your not backing out now.”

She easily pushed him back down and held him there with just a bit of weight. It was too awkward of a position for even a strong guy to get up from. She then started lining up the dildo to his man hole. she rubbed it up and down teasing it like a wet pussy.

He began to relax and she explained.

“Yea I figured it wouldn’t take much to get you back to what you wanted.”

She opened up his butt cheeks to examine her progress. She held on firm to her new cock and pushed firmly into his hole. Mike winced the whole way. She readjusted and pushed stronger into him. She was almost half way in. This is easier than she thought. Mike was in a small amount of pain but didn’t let it show. He wanted to muscle through it and get it over with. He relaxed a bit and Jill immediately felt a sense of ease. She practically slid right in. There was no further barrier she felt her belly against his ass. That was it she was all the way in. She stayed there for a minute ignoring Mike. She wanted to take over being in charge. She pulled out slightly and then slid back in slightly. Mike was busy seething through his teeth at the new found sensations.

“Your this far just go through with it.”

He felt her rare back again and plow into him. She didn’t care what sensation she was giving him she wanted to take on the act of a guy and give it to him like he did to her. Without any care in the world. She carried on pulling her ass out and then leaning her body into him again. She then grabbed a hold of his small put and made use of some handles. She had a good sense of how to use her new tool now. She started picking up the pace traveling that stiff plastic cock in and out of Mike. Picking up the pace she could feel less and less resistance out of him and moved to keep plowing into his ass.

She couldn’t help but picking up the pace and moving in and out of him getting lost in her own fantasies of being railed countless times by him. She was enjoying this new sense of being in charge and enjoyed giving him pleasure as well. She continued smacking his ass and pleasuring him drilling his ass with that woman’s touch of plastic cock.

Mike replied. “Harder harder, I think I can feel like I’m going to cum?”

She quickened the place ramming into him with faster speed. Even slapping his ass a few times to make it more authentic.

Mike felt weak in the knees and began cumming all over the couch. She picked him up off the couch and said.

“That was fun and all Mike but I enjoy it when you pound my pussy even more.”

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