Complexities

This new arrangement was going to really test us.

Was it strange that it was her idea and not mine? Follow up, I'm also okay with it? Maybe "okay with it" was the wrong term, but there was something niggling me about the thought of pimping my girl out. Letting her become a lady of the night to help us pay rent and survive in our new, big city apartment. Enjoy our new lives. The whole thing was fucking hot. We can't get away from the fact we are both curious, our heads can be easily turned both ways. I know I do it walking down the street, I know Livia does. We observe, we log and appreciate. We were both curious. Livia came home with a handwritten note, an idea, a full proof concept, as a solution to how we would cover next month's rent. I was honored she would do this for us

One morning when my Liv was already outside having her morning smoke, I plucked up courage and decided to have a little sit down and talk about it. I brought her coffee, made just the way I knew she liked it. As such my sexy nude girlfriend thanked me with smoke drifting from her sexy lips, with her luscious smile that made me go weak at the knees even now, before placing her cigarette back between her lips as she reached out for the coffee cup with both hands. She was something to admire, sitting on the outdoor cushion with nothing between it and her pert ass while her gently sagging tits were out on show as well. I just had to admire her nipples that were hard against the morning air as she placed her smoke in the holder of the ashtray and gave her hot coffee a careful sip before placing it down and looking at her laptop. She spun around, smoke swirling as she plucked it back up, so I could look at the screen. "Come see this! This pretty girl is offering a night for $500 and she has like a thousand responses! It's only been up for a few hours too..."

I peered at the dully lit screen and my eyes popped out on stalks firstly at the sexy girl, and secondly as I focused on the numbers of what she was talking about. "That would pay for a month of rent and the late fees," I mumbled, thinking about the price this woman would potentially get from all these willing men.

"I know... I think it could be something to consider," I could tell Liv was speaking carefully, as she exhaled the gray plume of smoke that came dancing out of her pink lipped mouth and swirled around her. I slowly nodded, I was only going to be adding to it as I lit up my own cigarette, moving to sit down at her feet, which she moved her fluffy pink slip on slippers onto my lap as if it were where they belonged, though a slight huff from out pooch, Dave, told me it was where he felt he should be..

He was wrong though, for me it was the perfect spot for her.

Placing my spare hand on her bare ankle, I began rubbing it with my thumb circling around as my thoughts spun in my head as I thought about it. Really, truly considering it for the first time. "I think... it wouldn't be that bad. I mean, it would be up to you at the end of the day. You have to be comfortable, it's your body, and you will be alone in some way with these men and... letting them have you." I quietly gulped at the thought. We had only ever been with one another, but the idea of opening things and sharing had crossed our minds here and there. Enough for this conversation to even be happening. "I'm... okay with it. We need the money too desperately for it to be off the table anyway. It was a long shot moving here, but I know you love it and so do I,"

I could see in her eyes that I was correct in my assumption. We both wanted to stay here badly and this was just a step in that direction. I was already okay with having my stunning girlfriend smoking naked on our balcony every single morning. Hell, I bring coffee to her so she can really enjoy herself. I was here to support my Liv, just as she supported me in so many different ways.

But after the chat, and focusing hard on the words we were putting down. We finally posted our own advertisement. It was shocking the kinds of guys that wanted to be with my Liv, a real high school sweetheart. My highschool sweetheart! The one that I went to both proms with and dated all four years. Aaron and Livia. The names rolled off the tongue. We were a power couple. Even more powerful at this point in my opinion. I like to think hers as well, but I have never been one to assume my lover's thoughts before asking the woman herself. We were lucky, I think, these men were not just perverse weirdos that were desperate enough to pay to have sex. The first guy to reach out to us was actually looking for a fun date to take to his older brother's wedding.

"How better to piss him and his prissy fiancé off than to bring an escort to his wedding?" He declared. My first time speaking with him on the phone gave me instant YouTube fuck boy vibes. As the conversation continued, Abel Lewis ended up being something of a beginning for me and Liv. Our emails pinged. The pictures he sent, with a handwritten note bearing the date and time, showed that he was a younger guy with dark chocolate brown hair that he kept long and in a thick bun on the back of his head. His body was lean and it turned out, I was not far off with my thoughts of him being a social media influencer. He was a streamer. One that would end up wanting more than just to take her to the wedding in the end, deciding to move their first date to the weekend before the nuptials so my beautiful lover could "volunteer" for his very first adults only livestream.

The day we found out about the new date, Livia was like a tornado going through every pair of her good pantie sets and whole closet. I sat back and enjoyed the fashion show I was given, seeing my love in all different states of dress. G-strings, thongs, lacy panties, long dresses, short ones for nightclubs. It took her hours to find the perfect thing to wear when she first met up with the man. Clothes she would only have on for moments after getting to his place. We decided on something simple, some tight jeans with a small black thong and an oversized sweatshirt that swallowed her up cutely. Even in an outfit like that, Liv had successfully blue balled me through showing me everything I had, but could not have that night.

He was clearly making a fortune from his livestreams. The money he paid Liv for the night had been more than enough to pay months of back rent in the pricey apartment. The one we thought we would be booted from just days before. It was a life changing moment to meet the towering hunk of a 6'1" man. Yes, and because I was 5'9" and dorky, I instantly got a complex looking up at him. The pang of something. I was letting him take out my beautiful girlfriend to fuck her. Not make love...fuck. Just knowing what could happen and that awful knowing that something could happen to MY delicate Liv. Or what could happen to her feelings for her blond headed, nature walking, science fiction loving boyfriend. It was obvious I was nothing like the hotshot streamer in the way of money or looks, but I knew my love and that she would come back to me. Just as she did both the night of the stream and the wedding.

What did I do while she was away that night? The first night of her with him, I could not help myself. I paced the floor plan for ages. Then I took a jog with our dog. I don't even jog! Made dinner. I even meal planned for the week, and then played solitaire on my phone. I did everything I could think of to distract myself until she was safely dropped back off with me. Then I knew this man would not hurt her or steal her away. I can't lie, I was disappointed, Livia seemed happy with the whole experience, explaining to me excitedly how she had been strapped into this sex swing and in front of what seemed like a million people at one point, as he delightfully ate her out. I had not seen her so joyfully post turned on in years. I had not expected the lick by suck and then fuck details as a highlights replay, but she was excited to tell me. At least she was not hiding anything from me.

After her story of the night, she calmed down and I guess feeling guilty sucked the soul out of me. It reminded me of when a few years back she finally got my cock down her throat the first time. Tonight, alone she was using that deepthroating skill as if she finally perfected it. If she had not, my love was fucking close and I couldn't wait to feel the height of that experience. Liv was sloppy with her love that night, both orally and vaginally. She rode my cock like she never had before and with the lust of someone I didn't know. Was her head elsewhere?

Between rounds in the sack with her, I had to message Abel and thank him. For the money and experience.

Then a few days later there was the night of the wedding. Letting her go was a lot easier this time, watching her get ready for that night and dress in a simple pale pink, floor length dress. Abel had sent her to a local store to have properly fitted that week. The dress was meant to not outperform the bride in looks, but to show off Liv with style. With the deep cut neckline that went right between Liv's tits almost to the belly button, it was showing off how plump and firm her breasts were. She looked lovely in every way in my opinion with her toned arms being shown off from the slender straps along with highlighting the ample cleavage.

There was no way Abel was keeping his hands off her, the evening of dancing practically nose to nose, the glow on her chest, the dress slid off her slim body no sooner were they in his car about to head to his home.

That night, I was very much alone until around noon the next day when my love was dropped back off at our place. As a distraction, I was working on an article from sundown to sunup, wanting to do my part in making some extra money as well. When she finally arrived at the door, it loudly unlocked, the thud echoing down the hallway. She stood there looking almost solemn, slowly slipping out of her tall gray, maryjane like heels at the entrance, leaving them right there. We finally met one another in the living room and before I knew it with a happy smile my love was in my arms. It was the morning of the night before, she was not wearing her lovely pink dress and makeup had been washed off. She had her hair tossed up in a messy bun atop her head and she wore an oversized sweatshirt, which I could only assume from the deodorant smell permeating off it was Abel's, and a pair of leggings he must have found for her.

On Sunday afternoon she took the longest, most sound nap I had ever seen from her. Maybe after nocturnal activities this was what my sweet girlfriend needed to be able to take a proper break every now and then. All these men for her to take care of, and I was conflicted on my feelings about that. But, passing by her angelic, peaceful form all curled up on the couch inside Abel's big shirt with one of our faded out throw blankets over her lower half, I knew I could deal with my own baggage. Livia deserved this kind of satisfaction.

The next customer was a friend of Abel's so I really didn't think much of him. We had still been in contact with the streamer and even gone as a guest to a couple events he held. It was like we were in the upper echelon of society around him. Abel really had it all and he was generous with his wealth and joy. Most of his functions had a charity attached to it that all his rich friends would be throwing money into all night long. I found it useful, mostly just to see who would be the one giving the most, and those who seem to have very little contact with Abel Lewis himself. We met this new guy at the last event, a deeply wealthy man, Damian Saunders. We did not know where his money came from and as we did not ask, he did not give us that information right off the bat. Damian was a quiet, and at 6'2 a massive man. We would later find out his stomach was fitted with rippling muscles that even put Abel's body to shame. Hell, I was a whole decade younger than the two of them, and at twenty-three and they both out did me in that department.

Imagine how I must have felt about these guys, with my Liv.

Emasculated. Worried. Jealous.

I was all of those things, but those were not the only feelings I had towards them. There was this nagging feeling. I was also curious. You know I have only ever been with Liv, my first. BUT there was something else. That curiosity. I always knew I wanted to be with a man one day. I guess I just never found one I liked enough. Liv would tease me all the time when either walking down the street, or we would be swiping through Tinder together and I found zip. She told me I would never find a man with my high standards but... I had at that point.

Abel.

It was insane. My girl was having sex with this guy for money. The dollar we needed to live. There I am more than feeling jealous of him. Yes, I was jealous of her. Who would have thought that was how things would turn out?

The day of her date with Damian, the mystery millionaire, I had not yet even told Livia about my feelings. Only because she seemed more nervous about this night of paid passion, than she had with Abel. There was something so inviting about the streamer and that was pretty obvious as for how he came over early that afternoon to help her get ready and chill with me. This was another event and she had to be dressed to the nines. Abel knew of a friend, Emilia, who was a makeup artist and for all her skills, Livia could use all the help she could get in that department.

Especially when it came to these Hollywood style events.

So, as she and the young blond woman were tucked away in our small single bedroom, me and Abel headed outside on to the balcony for a drink and for me a much needed smoke. We were both unfortunately addicts when it came to nicotine. Partly why we chose the apartment with a balcony. Although several times I had tried together with Liv quitting and even vaping. I was still stuck with them. No matter how filthy and unhealthy they were. Two of Liv's lipstick covered butts were stubbed out in the ashtray in front of us. She had already needed to smoke before and during the makeup. I was surprised. It seemed even the woke minded Abel Lewis was in the same boat as he stood next to me with smoke swirling around out on the deck.

"So... what do you know about Damian? More than we do I hope," I asked, leaning against the railing with my half smoked cigarette between my fingers and a nearly empty can of beer in my other hand. Abel chuckled and shrugged a little, "I don't know too much. He keeps a lot to himself, but he is an explorer type." He smiled with a twinkle in his eyes, "I wouldn't be too shocked if he starts trying to take Liv out to these distant lands. He goes all over. Has lots of fun little stories and seems like a cool enough guy. Always generous at events and somehow active online as well,"

That was... not quite what I wanted to hear. Nor the encouragement I needed. I knew Liv was smart though, and a good judge of character. Not any worse than I would be at least so if she wanted to go through with this I was going to support her and then worry and stress from afar. I hoped the worry would go someplace good. The energy of it that was. "This must be a hard part for you... I'm sure Damian wouldn't mind if you came to just make sure everything would be okay," As the sentiment came from Abel's mouth, I shook my head and sighed. "It would be worse I think... To watch her be with Damian it would be... too hard. He's actually kinda her type I mean, the blond hair and glasses already but he's also like... creepily nerdy in a way. A fitter, sexier version of me. He might be a cool guy, there again he might be a real weirdo. Just have to figure it out for yourself in the end,"

The smoke hung in the still air on the balcony between us. There was a silence before Abel started laughing at the way I put it, shaking his head, "So, does that make me one of those creeps as well?"

I blushed. "I mean... you did answer our ad on that forum website that hasn't been updated in like a decade, maybe two?" That put the world back to rights. He knew it. A site like that was obviously seedy if the creator made it and left it as was since the early 2000's.

We soon finished our smokes while still laughing about the last comment, both knowing there was no way for me to be completely ready for Livia to be alone with what amounted to a stranger. I just needed to be okay with it in my core, not just surface level. Nine times out of ten, everything would be okay. There was no point in being afraid of the one time it didn't.... Right?

Going in we were met with the girls already out of the bedroom and Emilia walking around Liv and making sure everything was perfectly in place. Every single thread of hair was tied down. Liv looked stunning, enough to have my jaw falling open. Somehow, even though her breasts were far better covered this time by a beautiful light blue bra which could be seen under a see through, lacy blue top. It only covered her as much as a short sleeved cropped top would. I was utterly entranced by the lacy, delicate design of the hem. I could not help myself as she came closer to me by reaching over and running my fingers through the dipping, arching, and dangling fabric that covered her tummy. A high waisted skirt of the same baby blue color was a perfect match with the top. There was a thigh high slit as it wrapped around her torso and synched nicely. Her shoes were these strappy dusty pink heels that put her just about at my height.They tied into a pretty bow on the back of her leg, right above the ankle and they showed off her freshly done toenails that matched with her manicure. She was looking fabulous.

Somehow my attention was able to be taken by the other women in the room. The curvy blond with her hair pulled back in a high ponytail and a dark green cropped, skin tight tank top with obviously no bra under it. There was not only that though that took my attention. No she also had her round, jiggling ass out on show. She was either going commando or wearing the smallest g-string under her matching thigh waisted drawstring shorts. She was very busy still prodding around my love, kneeling down to fix the bottom of the dress and it seems to give us a good look at her bottom tool. I could not help myself but see the way her ass creased against her thigh as she bent over with her round butt in full view of me and Abel. When I glanced over to Abel, looking for male solidarity, he seemed unfazed, giving an appreciated nod with a brief upturn of his lips as he flicked his eyes at the view before refocusing on the phone he was holding in his hand.

There was no surprise behind my looking and appreciating the 'art', which showed itself in front of me, when I did nothing to hide it. I was standing there staring right down at Emilia's buttocks practically undressing her in my mind, and I was lost in the moment. Liv's eyes bore into me. "Aaron?" Her voice was gentle and held nothing but a laugh under its tone. She was not angry with me for my leering. God, I was a blessed man. "She did a really good job right?" My love asked, bringing me back to the moment. My eyes slowly moved up her leg and to her waist. "Yea, babe..." I trailed off as she reached out and grabbed onto my chin, forcing my eyes up to her face when I realized the detailed makeup look that had been done as well. It almost looked like Livia had a photo filter permanently over her face and it was actually really magnificent. Especially considering the small amount of time they spent back there together. "Oh shit... you look stunning, babe!" She perked up at the compliment and even giggled a little, giving me a knowing look. If anyone knew what it looked like for my eyes to wonder, it was my girl.

"We need to get going. Damian is gonna meet us at my place for it. You two sure you don't wanna come?" Abel asked, coming over and taking Liv's hand.I leaned in and carefully pressed a kiss to her rouge colored glossy lips before pulling back in time to see Emilia's phone fall out of her pocket and onto the floor as she stood up again. Her little shorts that had baggy pockets already full with makeup and brushes.