Chapter Text
After the airplane left for Italy with the rest of the group, Andrei was left standing at the airport alone with Olga. “Well, since you decided to stay with me here after all, I guess we gotta see where we’ll stay tonight. If you want we can stay at my mother’s place again. I’m sure she would have no problem with it.”
Olga chuckled at that. “Oh Andrei, I think a hotel would be much better for tonight. We still have to finish what we started and I doubt we will get to that sleeping in the room next to your mother.”
Andrei blushed slightly. “Oh, hehe. Well, if you want to keep going I’m all for it. I just hope I don’t end up locked in and naked again.” She hooked her arm around him and leaned in playfully. “Don’t worry, I won’t leave you alone again while you’re naked. I’ll be there all the time. But don’t think that means you’re in control suddenly.”
With that said, the plan for the evening was set. After spending some more time around the city, accompanied by Andrei’s charming improvised guide information, and having dinner at an expensive restaurant, they made their way to the hotel where they would be spending the night.
As soon as he closed the hotel door behind them, Olga was ready to go. “Now, listen, I’ve got some stuff with me that I planned to use the last time, you know, before I found out you were secretly a cop. Well, I’ve forgiven you enough that I’m here again so let’s try it now.
You’re gonna have to jump over your shadow here a bit I’m sure, but trust me, if you do it’s gonna be the greatest evening you’ve ever had. So, I’m gonna get changed, and you’re gonna get naked on that bed.” Andrei could only nod in alight confusion before she disappeared into the bathroom with a bag and a confident smile.
He didn’t quite know what he should expect, but he loved her assertive personality. It was energizing and refreshing. He found it exciting to see what she wanted to do with him and so got to work obeying her command right away, stripping completely naked and lying down on the bed, his back leaning against the headboard.
As soon as the bathroom door swung open again, his eyes widened in surprise. He wasn’t even really sure what he was seeing. Olga was smirking at him mischievously. She was wearing a sleeveless leather vest and a pair of black leather gloves, while further down, a suspiciously phallic object was hanging from a sort of harness.
The need to clear up the mystery was stronger than the willingness to not ruin the mood. “Ok, I miiight need at least a bit of explanation about what exactly we’re going to do.” She chuckled at that. “Oh, sure.” She grabbed her dildo with her right hand suggestively. “I’m planning on putting this inside you, from behind. I’ve done it before with other guys. Almost always hesitant at first, almost always loved it by the end.”
Andrei was blushing really hard now. “H-how does that… does it… hurt?” She came over to the bed, sitting next to him now and he noticed she was holding some other things in her left hand as well. “It doesn’t if you do it right. And I know how to do it right. It’ll take a bit longer the first time, you need to really relax for it to be good. But I’ll make sure that you are.”
That really reduced his anxiety. He had of course never done something like this before, but that kind of made it more intriguing. Especially her sense of authority and confidence turned him on. It made her feel safe, trustworthy. If anyone could make him enjoy this, it was her. “That sounds good to me. Just tell me what I have to do.”
She smiled happily at him and started running her cool leather gloves across his body. The texture softly stroking across his skin made him feel as if he was melting into her touch. “The best way I’ve found is for you to get on your hands and knees with me behind you.” She pushed slightly into his back.
Following her direction, he moved forwards. He didn’t completely like the fact he wouldn’t be able to see her like this, but he also wasn’t prepared to go against her clearly better judgement. Starting with a soft slap to his ass, she began to kneed his cheeks with her cool gloves for a while, before one hand left him again.
He could hear her fidgeting with something before her finger returned, coated in a slick substance and began to slowly massage his anus. At first, he noticed himself tensing up involuntarily, not used to being touched there by another person, but slowly he managed to relax into the touch again.
He still let out a small gasp of surprise when her finger entered him for the first time. Over several minutes, she continued to stroke his body with one gloved hand while the other was moving inside him, stretching out his entrance first with one and then then two and even three digits.
Although she hadn’t touched his genitals at all since they started, he could feel himself becoming hard from the experience. Shortly after, the movements stopped temporarily. “I think you’re ready for the big event, hmm?” His answer only came in the form of an excited moan.
With that, she pulled her fingers out of him, only for them to be replaced by the tip of the dildo strapped to her hips. The slick object was pushed into him slowly. It wasn’t much thicker than her three fingers had been, just quite a bit longer.
Since she now had two free hands, she used one to hold onto him while the other finally moved to his dick. At this point she started to slowly move her hips to pull out and push back in time with stroking him.
He could quickly feel the pressure building up inside him. The synchronized rhythm made it feel like it was just one movement and something inside him was responding very strongly to it. His enthusiastic moans were eventually cut short by a guttural groan as an orgasm rocked through him. The spasming of his muscles while she was still inside him made for another very unique sensory experience.
Afterwards, she slowly pulled out of him, as he collapsed exhausted onto the bed. “I told you it would be amazing.” Her tone was both teasing and proud. “It’s pretty intense, hm?”
With a sigh, he managed to roll himself onto his back, a mess of sticky cum on his stomach. “Yeah. Let’s maybe do something else next time. But, the time after that I’d love to do this again with you.”