A Promise is a Promise

"Honey! I did it! I passed the exam!" were the first words Sean heard after the door to his apartment opened. He sat on the couch in the living room and binge-watched yet another Netflix show when his girlfriend Mary barged in and jumped on his lap. Without giving him as much as a second to reply she pressed her lips against his, her red hair covering their both faces for as long as the kiss lasted.

"I did it! An 'A' again! I'm officially done with exams for this year! Aren't you proud of me?" she beamed and planted another kiss on his lips, her hands on his cheeks.

"Of course I am! Thiiiiiis much!" Sean chuckled and showed with his arms just how proud he was of her. Unlike him, Mary still had a year to study at her college and was very worried about good grades. Being a good boyfriend, Sean always supported her and helped her in any way he could.

"Soooo, do you remember what you promised me?" the gleam in Mary's eyes made Sean gulp and his face got hotter.

"Uhm... yeah, sure, of course. A promise is a promise!" he forced his smile to stay even though deep inside he felt the coldness creeping in. It wasn't that bad of a promise, he thought, but still...

"Yay! Thank you so much, honey! I love you!" Mary hopped up and down in his lap and gave him a hug so tight and loving that all second doubts disappeared from Sean's mind.

***

The coming Saturday, though, the thoughts came back. Especially when he lay on his and Mary's bed, nude as the day he was born and waited for his girlfriend to come back from the bathroom. While he listened to the sound of running water he reminisced about the deal he and she had some time ago. Whenever exams came closer, Mary became worried and anxious about whether she would pass and whether she learned enough. The latter part was especially troublesome for her because she had problems with sitting down and just learning. Which made her only worry more and learn less, a vicious circle she had no idea how to escape. One day, in his attempt to help her and calm her down, Sean hugged her and told her:

"Darling, I know how to motivate you! What if I tell you that if you pass the exam I will buy you that Bad Dragon dildo you wanted?" As soon as he finished the sentence he knew that he pushed the right button. Mary's eyes sparkled and widened and she asked at least five times again and again whether he was serious about it.

This unusual offer worked because Mary was definitely the kinkier one in their relationship. As much as Sean enjoyed the shared intimate moments, oftentimes he had to hold his girlfriend back to not go too crazy. The thing with the dildo was one of those moments. Mary eyed the toy for quite some time already, but Sean was concerned to not let her fall into a rabbit hole - she already had half a dozen normal dildos and vibrators, not to mention a small collection of buttplugs, and he was afraid that once she would lay her hands on a Bad Dragon toy there wouldn't be a way to hold her back. But as long as that meant that she would calm down and actually learn for the exams, he was ready to risk it.

As it turned out, this kind of deal was exactly what Mary needed to get motivated and a month later she proudly unpacked the silicon cock of some fantasy creature. After that Sean made more and more offers and always made sure to deliver whenever his girlfriend would bring home an A. A quickie in a parking lot in the middle of the day; sex in the park while there were still people around; a pinky up his butt during a blowjob; a visit to a nudist beach; some light BDSM play - again and again, he agreed to participate in yet another one of Mary's kinky fantasies and so far he had to admit that it was more fun than he would imagine.

He wasn't that sure about his last deal as he saw Mary enter their bedroom with almost nothing on. Almost. Most of her body was nude and for a second Sean forgot about everything else as he admired her well-shaped figure. Red hair that reached all the way down to her waist and that she let flow down freely. A pair of breasts, perky and just the right amount to fit in his palms, with a pink hard nipple on top of each that begged to be sucked on. Pale skin with just the right amount of freckles on her smiling face. Round hips that swung from side to side with every step. Sean felt his flaccid cock twitch and usually, it would be hard already, but his enthusiasm stayed within limits as he saw a pink strap-on dangling between his girlfriend's legs, covering her sex and held in place by black straps around her hips.

This was what he promised her for passing her final exam. His anal virginity, taken on their bed. And now that promise caught up with him and however strong his love for Mary was, he still wasn't 100% sure that he made the right decision. Apparently, his thoughts were visible on his face for when Mary crawled onto the bed beside him, she stroked with the backside of her hand across his face and kissed him on the nose.

"Don't be afraid, love, I'll be gentle. Just give it a try, I'm sure you'll like it!"

"No, no, it's fine. Let's do it. I think I'm man enough to get fucked in the ass by a hot woman!" Jack joked to ease his nerves.

"Just relax," Mary said and kissed his neck. From there on she moved further down, to his chest where she licked over his nipples and gave them a playful bite. Jack moaned lightly, even though somewhere in the back of his mind he could still register the silicon toy brushing against his leg as Mary moved along his body. Once finished with Sean's chest, Mary moved towards his belly, her hands already playing with his thighs. Further and further south she went until her lips touched the shaft of her boyfriend's manhood.

"Still nervous?" she asked gently, commenting on the still soft state of his flesh. With a smirk she stuck her tongue out and gave the cock a slow lick across the whole length, forcing another moan out of Sean's mouth. Her fingers wrapped around the base, soft and warm, she covered her favorite toy with small kisses and little nibbles. Mary knew where Sean's most sensual points were and soon she felt the blood rushing inside his dick, making it harder by the second. "There we go!" she talked to the growing inches in her hand and wrapped her lips around the purple tip. Moving her hand rhythmically up and down, she sucked and licked on Sean's erection until it stood to full attention and twitched, silently asking her to continue.

"And now, let's do it!" Mary's voice was full of joy and she giggled as she took a kneeling position between Sean's legs and took a bottle of lube. His breath shallow, Sean watched her open the bottle and pour a generous amount of thick goo on top of her artificial cock. With an experienced movement, she spread it across the pink toy and put a big drop on Sean's tight muscle. He shivered as the cold from the lube made his pucker twitch and took a deep breath, telling himself to relax.

"P-please... be gentle..." he couldn't stop the words coming out of his mouth as Mary pointed the tip of her silicon dick towards his backdoor and pressed the tip against the little hole.

"Don't worry, honey, it's going to be alright!" she assured him and began to push.

Sean clenched his teeth and grabbed a fistful of blankets as he felt his ass spread, unable to resist Mary's persistence. He knew that the strap-on was smaller and thinner than his cock, but right now this piece of information didn't help him much as he felt his not-so-virgin-anymore butt to give in. The first inch went inside almost without any trouble, but then he felt more and more resistance inside of him and grimaced.

"Are you okay, honey?" he heard Mary's concerned voice as she stopped moving. His first instinct was to tell her to stop the whole experiment, to never do it again... but then he looked into her sweet face and knew that he couldn't disappoint her at this point.

"No, no, it's alright. Give me a second and then go on," Sean nodded as he took another deep breath. Some seconds later Mary moved again, rocking gently forward and backward and with each thrust, the pink dick moved further inside Sean's anus. At some point, the tip hit something inside of him and Sean's eyes widened as he let out a sudden moan. He looked, bewildered, at Mary.

"Did... did it feel good?" her eyebrows lifted, Mary's lips curled into a smile. She took him by his thighs and did another movement backward and forward. "Does it feel good there?"

Another moan came out of Sean's throat as some unknown point in him got stimulated again. He was too absorbed with the strange new feeling to describe it properly, but it was as if someone put an erogenous zone inside of him and was now stimulating it over and over again. Mary's smile got wider as she saw the look on his face and she continued to grind back and forth, eager to see what motion would make Sean moan more. Minutes passed and with each of Mary's thrusts, Sean got more and more used to the stimulation inside his butt. Reluctant at first, he now moaned without traces of embarrassment.

"Mmhmm... nnghhhh... Shit... d-deeper... go deeper, please..." he whimpered as the tip of the artificial cock hit his magical spot once again.

His girlfriend didn't need a second invitation to that and put more weight into her next thrust. The strap-on went some more inches deeper inside, now almost completely hidden in Sean's body. His prolonged moan was all she needed to carry on the fucking. The other end of her toy pressed against her clit whenever she pushed it inside her boyfriend and made her moan together with him, the sound of their shared pleasure filling the room. During the whole time, Sean's member stayed hard as iron. Whenever the strap-on brushed against the P-spot a drop of precum dripped out of the mushroom tip and over time there was a little puddle of the clear fluid on his stomach.

"Please... please, Mary, I need to... to cum..." Sean began to beg after some endless minutes of pure bliss. As good as this new position felt, Sean's cock just couldn't overcome the final edge. It twitched and jerked with every thrust and Sean felt the pleasure build up in it, but it was never enough to make him finish and he couldn't take it anymore. "Please!" he half-moaned, half-screamed in agony.

"Aaaaw, poor baby! Why didn't you say so before?" Mary was sympathetic and wrapped her soft little hand around the erect rod. Using it as a handle, she continued to pound her boyfriend and simultaneously jerked him off.

Sean howled in ecstasy as he finally got the proper stimulation he craved so much. It took Mary just half a dozen tender strokes before he reached the point of no return. His back arched, forcing the strap-on one more time deep inside of him, and a first powerful shot of cum came flying out of his trembling cock. It flew in a high arch and before it could land on top of his chest another one came right after. Sean could feel how his girlfriend didn't stop moving during all the time, adding more and more pleasure to the colossal orgasm he experienced.

This climax was hands down the heaviest he ever had and shattered his world. Sean couldn't remember ever shooting so much goo in one go, let alone that it ever came out with so much power. Some drops even made it all the way up to his chin, but he lost all connection to reality to notice such a thing - his whole world right now consisted of his orgasming dick, his girlfriend's hand pumping it, and her silicon cock penetrating him again and again.

He must have spaced out for some seconds because all of a sudden Mary's face was right in front of him, her tongue lapping up the few drops of cum from his chin.

"Mmhmm, looks like someone had fun!" she winked and gave him a deep French kiss. "Wasn't that bad, am I right?"

As much as Sean wanted to answer her all he could do in his state was to shake his head and look up into Mary's green eyes, full of happiness.

"I love you, honey!" he heard her saying before she kissed him again. He knew that this wasn't the last time they would play like this.