Teaser: Ian moaned again.  "Yes Abby, fuck my ass" Abby did as she was begged to do and thrust her fingers into his ass. After a few minutes Ian perked up and asked "Would you ever consider pegging me?" Abby only gave it a split second of thought before answering "Fuck yes I would."

Abby and Ian had just spent the last three nights together and tonight was the last day of their vacation. Both of them, despite being so attracted to one another, had almost hit their limit with sex. Abby had joked about never having sex five days in a row before and Ian had kept his promise to change that four days in a row so far as they had had sex that morning. Both of them agreed that if nothing happened tonight the trip had still been fun.

After talking and cuddling and a couple of shared alocholic drinks Abby asked Ian if she could give him a full body massage. She absolutely loved to feel his body under her. The muscles in his back, arms, and legs would tense and relax as she ran her finger tips over every inch and it gave her the shivers.

Ian quickly agreed and got completely naked. Abby straddled him but before she could get too far Ian said "Hey, it would feel better if you were naked too." Abby giggled "You're right, it would" she said as she stripped off her clothes and got back up on the bed.

"Mmmmm" Ian moaned as Abby's bare legs squeezed his hips and her crotch came to rest just above his ass. "See, that's much better" he said. Abby just gave his back a little kiss and started to move her hands up and down his body.

She was enjoying looking at his tattoos. Feeling his strong arms and pushing her fingertips into his skin. She slid down slightly so that she should massage his glutes and legs. She even turned around for a few minutes so that she could properly do his calfs and shins.

Regardless of Ian being on his stomach she made sure to reach around and massage his quads. They had been doing a lot of work the past few days while he had fucked her senseless. She could feel how tight he was and took her time on each leg on individually so as to really loosen him up.

She could tell how relaxed he was getting, not quite falling asleep but resting. She loved to see him like this, knowing that she was bringing him pleasure and comfort. He looked so incredibly sexy. The hard lines of his face melted and she could see the young man he still was. More carefree tonight and not yet worried about getting back to reality in the morning.

Looking at his body, his tattoos, his black hair with flecks of silver, feeling his worries and cares melt away under her, Abby became incredibly turned on.

Earlier in the night they had talked about some of the wildest things that they had ever done sexually and Ian had confessed to her that he occasionally had enjoyed anal play with himself but had never done anything with a partner. He had told her this before but that night he had gone into more detail tonight and Abby was in awe.

She knew he liked a little anal play. She had even bought a small beginner anal toy and anal lube specifically for him and surprised him with it the night before.  Her purchase had also come with a free gift of an above average sized, standard silicone dildo that she had hoped Ian would use on her as an introduction to double penetration with a partner.

What she didn't realize though was that the idea of Ian being into anal play was actually a turn on for her and that he was no where near the beginner that she thought he was.

She continued to touch and massage his body as she thought about how she had used the new toy the night before to penetrate him. Her pussy become wetter and wetter and she decided to take chance and began to rub more of his ass, gently spreading his cheeks.

She leaned forward and starting at his shoulders she kissed all the way down his back to his hips moving her hands along his body as she kissed him. She moved back toward the middle kissing as she went, using her hands to spread his cheeks until she got to the crease and she gingerly kissed his tight hole.

Ian let out a small noise of either pleasure or approval that Abby very much liked. There was no smell or taste that Abby could notice so she decided to keep going and stuck her tounge out just slightly to give it a lick. Another positive noise came from Ian. She made the decision that she wanted to keep going, she licked his balls all the way up between his legs and ass to the small of his back.

Ian moaned and shivered. that was hot Abby thought "Did you like that?" She asked, already knowing the answer.

"Yes, that was very nice" he said in an almost breathless voice.

She wanted to do more. They had talked about boundaries multiple times and Ian had said he was comfortable with her rimming his ass as well as penetration with one finger. Anything more would need additional consent, but she wasn't worried about crossing that tonight. Or so she thought.

She continued to massage his back and ass, gently pulling his ass cheeks apart occasionally and licking him again. The way he started moaning really turned her on. The light buzz from the couple of drinks also was helping her relax into it as well.

She then started to rim his ass. She licked it and swirled circles around his hole pushing her tongue against his entrance. His ass was so wet that her tounge pushed past the entrance and she knew she wanted to give him more.

She licked his ass and left it nice as wet as she moved down to his balls. She then sat up on her knees, pushing them up and under his ass slightly. Sinking down to rest on her legs.

From this position Abby had great access and took her left hand an spread his ass which he had instinctually pushed up to stay in line with her hips. She sucked on her middle finger and then put it up to his ass hole. She leaned over and whispered into his ear "Are you ready?"

"Yes" he said, his voice dripping with anticipation and excitement. Not a single drop hesitation crossed his lips.

Abby felt his enthusiasm and slowly pushed her finger in. As she did Ian let out a slow low moan of pleasure. Her pussy started to drip and her clit tingled. His pleasure coming from her was turning her on even more.

She started moving it in and out slowly at first. This was the first time she was actually fingering him and the sensation was new. The coordination was new. This was the first time she was on the giving end of fingering at all, with anyone. But fuck, she was having fun and he was enjoying himself too.

She kept adding more spit and decided to switch from using her middle finger to her first finger. This allowed her to push in a little deeper as well as find a new rhythm. Once she had made this switch she attempted to lean down and kiss and suck on Ian's balls. She succeeded but then would stop fingering him.  She tried using her left hand to touch his cock or gently scratch or tug his balls but again couldn't quite get the coordination right. 

Instead of trying to do multiple things poorly she decided to focus just on his ass so that she should continue to bring him pleasure that way. As she pushed back up on to her knees she felt Ian push his hips back too, lifting his ass to be in line with  hips. Ian had gone from lying prone to tucking his legs so that his ass was slightly in the air. Abby spread her legs behind him so that her quads were up against the back of his thighs and the outsides of her lower legs were pressing into the insides of his.

She moved her hips in rhythm with he fingering him. Ian moaned and pushed his ass back against her hips. She continued this motion for a while just enjoying the moment.

As she bent down to rim him again and add more spit she had an idea. She bent over and asked Isn gently in his ear "Do you want two fingers in you ass tonight?" Without skipping a beat Ian moaned and replied "Yes"

"I know you're more experienced that what I originally thought but I'm going to need you say you want it" "Yes, Abby I want two of your fingers in my ass" "I can do that"

Abby pulled out her finger and licked Ian's puckered hole making sure to get it nice and sloppy before sliding back in, this time using her middle and first finger together.

Ian moaned again.  "Yes Abby, fuck my ass" Abby did as she was begged to do and thrust her fingers into his ass. After a few minutes Ian perked up and asked "Would you ever consider pegging me?" Abby only gave it a split second of thought before answering "Fuck yes I would."

This gave her a new idea though. "Ian, can I fuck your ass with the toy is used in you last night? " "Absolutely" he responded.

She went to grab it as well as the lube and brought it back over. It wasn't large though, certainly more narrow than her two fingers, but it was a bit longer. She put some lube on and slid it into his ass with little force as the soft jelly material tried to bend awkwardly.

"Mmm, do you like that?" Abby said as she began to move the small plug in and out. Ian hadn't moan or really made any other noises, she continued but the small, soft toy wasn't really doing what it needed to do. It was meant for a beginner to anal play. And after their earlier conversation, Abby knew he was by no means a novice.

She pulled the toy out and stepped off the bed, quickly grabbing the larger dildo that she had mean for Ian to use on her but was still in its original packaging. Ian looked back and saw what she was getting. They made eye contact and Abby gave him a quick smile and Ian put his head back down, leaving his ass in the air.

Abby climbed back on the bed and knelt between Ian's legs again. She kissed his back and ass a few times, running only her left hand up and down his body. She then applied a generous amount of lube to his tight hole and the dildo. She lined them both up and then lined her hips up to his.

"Ian, I'm going to fuck your ass with this dildo. Is that something you want?" "Yes" he said, but there was a fraction of hesitation in his response. "I won't if you don't want me to." Said Abby as she leaned her hips back alowing the slight tension of the dildo to his ass to loose pressure.

Ian looked back at her eyes and said "Abby, I want you to fuck my ass. Please fuck my ass? I want you to. I need you too!"

This is what she wanted to hear. Usually Ian was the one in control, he was the one who gave her pleasure. He needed that control to cum and this time he had to give that up to get what he wanted. It made Abby feel powerful to know that she was the one in control.

She had never thought of herself as dominant, in any bdsm quiz she would always score between a 98 and 100 for being a submissive. This was totally new and she kind of liked it.

"Yes, Ian, I will give you what you need" she said and very gently and slowly pushed the silicone member against his enterence until it stretched from the pressure to accommodate the incoming object.

Ian let out a low moan and breath as the dildo, which was well above the size of an average cock, pushed its way inside of his body. While he wasn't new to anal and this was not at all the largest thing that had ever been inserted, it was certainly the largest thing to enter his ass any time in the past few years.

"Oh fuck" he said as he felt Abby pull the dildo back out slightly before pushing it in deeper for a second thrust. He loved this feeling, especially if he could have been jerking off his own dick right now too, but in this position his hands were under him, holding himself up.

Abby slid the dildo in and out a few times and then added a little bit more lube. It was obvious that Ian wasn't use to having anything inside because his strong muscles kept pushing it out. She basically didn't have to pull it. She would push in and he'd push it back out. Perfect so that she didn't need to use her hand as much and instead placed them on his hips.

She kept her two first fingers up and off his skin, they looked clean but she didn't want to touch him with them. This was fucking hot seeing Ian take a dildo meant for her in his ass. She knew he was enjoying it even if he cock was still not fully erect. She started to push her hips up against his ass and found a gentle rhythm.

"You enjoying this baby?" She asked "Oh yes, I just wish you could enjoy it too, I wish I could feel you cum all over my ass while you fuck me"

That statement turned Abby on so much. She wanted to cum, she needed it. She started to rub her clit with her left hand and she still used her thumb and last two fingers of her right to hold onto Ian. She wasn't being gentle with his ass any more, but every sound Ian made was one of pleasure.

She kept going, enjoying her own dominance and the sounds he was making. She wanted to please Ian in every way. She knew his pleasure came from hers and wanted to cum for him. She rubbed her clit faster and finally pushed over the edge.

Ian knew Abby's body and sounds so well that the moment before she came he growled a low "Yesss" and then felt her squirt her juices all over his ass as her body locked up and she let the dildo push fully out of him as she came hard.

Abby was in shock and had lost herself when she came. Her head spinning and seeing stars from the incredible orgasm she laid down and motioned for Ian to turn over and lay with her

"That was incredible" she said. "Yes you are" he replied. She just smiled and mumbled "we are"

They lay there for several minutes just holding one another and enjoying the moment.

Eventually, they got up. Abby throughly washed her hands and the toys, spraying them clean and leaving them to air dry next to the sink. Ian showered and Abby joined him. Moving back to the room, they laid down in the secondary bed that was still nicely made and drifted off to sleep.

The next morning, Ian woke up Abby with a hard on. She had been promised sex for five days in a row and Ian was not the kind of man to back down on a challenge. They fucked with passion but quickly. Ian still managed to get Abby to cum four times before the fifth time he came with her.

They got ready at their own pace, not having to rush and gently and lovingly said their goodbyes as neither one was certain when would be the next time they would see each other. They took their luggage out to their cars and hugged and kissed one last time. Reality was now here and they had to return to their normal lives.