Favors

*** Note: This is a fictional story, all characters are over 18.

I met Hailey in college, we were both involved with the swim team. There was something about her from the first time I laid eyes on her. The story will veer from the expected as I describe her. She is nearly flat chested, not much in the way of curves and at first glance you might imagine she'd fit into one of those silly boxes labeled 'excellent student'.

At the time, she struck me as someone that would be approachable, and not overly concerned that her friends might give her shit over talking to a guy that didn't measure up. She was almost exactly that. Her easy-going personality won me over quickly and we became a couple. Hailey stands 5'7" tall, just an inch shorter than me. Her raven black hair has this uncanny ability to always fall exactly into place framing her face which perpetually has a smile that is infectious to anyone that sees her.

She wasn't 'out of my league'. She didn't have perfect huge tits, or an ass to die for, she wouldn't ever be mistaken for a runway model but none of that ever mattered to me anyway. Hailey always made my life better. I couldn't be upset for long around her, I couldn't stay depressed over anything as long as we were together. She was like the best therapist in the world, you didn't even need to tell her what was wrong, she just had a way of fixing it, whatever it was. I knew before the school year was out that I'd ask her to marry me, but only after we completed our degrees.

My name is Mark, I come from a humble family that has always worked hard for anything we've accomplished. My parents both worked and Dad was often gone for a week at a time. It was just normal for me. Mom was always around though, aside from her job working in a Dentist's office, she was very involved with normal housewife activities, she never missed a swim meet, and if my Dad was home at the time, he'd join her in the stands. My life was probably more boring than many other folks have but that was fine with me. Women tended to find my blonde hair attractive, and I suppose I'm a decent looking guy, slender, typical swimmer's body. I guess having to perform in front of people helped with having the courage to interact with people, so I wasn't terrified to chat with women that had regularly led to having relationships (although never for long periods of time.) All in all, I have no complaints at all.

After graduation I asked Hailey to marry me, and a year later we were man and wife. As we both worked we weren't struggling financially, and our work schedules were nearly identical so we didn't miss time we could have spent together. I suppose during that first year I couldn't imagine things being much better. Our sex-life has always been quite active and we've experimented with some mutual interests, one that stands out was a desire to have sex in a public place. We've done that on a number of occasions and we were very nearly discovered the second time we did this as Hailey rode me in the front seat of my car in the parking lot of a very large nationwide retailer, ahem.

I came home from work one Friday, I typically arrived home about 15-20 minutes before Hailey. I knew we'd be going out to dinner that night so I avoided the refrigerator and whatever snack I'd talked myself out of just as Hailey came through the door and asked me to do her a favor.

"Sure, what's up?" I answered, and watched her curiously as she seemed to be reluctant to actually tell me what the favor was.

"This sounds so weird," she said while shaking her head from side to side "let me just show you."

She walked over to me, tapped on her phone and held it out to me. I looked at the screen and there was a picture of a dark haired woman, with her hair pulled back tightly in a ponytail, with her tongue against a blonde-haired guy's tongue. It was a profile photo, and while that isn't especially risque, what made the photo unique was that both the woman and the man were wearing the exact same kind of lipstick. Their lips seemed to be covered in a very shiny, glossy wet paint. I'd seen Hailey wear similar lip color on occasion, but usually when we were going somewhere fancy.

I handed her phone back and shrugged, not understanding.

"I want to do this with you." She said, rushing the words out and I suppose maybe thinking that would be the one way she'd have the courage to ask.

"Hailey..." I started, and watched her face. She seemed nervous and maybe embarrassed.

"I just think that picture is so... I'm not sure how I can explain it. It's really arousing for me to see it. I'm not seeing it like a woman kissing a guy that wants to be a woman, it's just hot to me."

"You want to put lipstick on me, and kiss like in the photo." I stated the obvious.

"Mark, I won't bribe you. I just want you to know I'd have a really hard time telling you 'no' if we could try this, just once." she said, and the happy smile on Hailey's face transformed into a 'Do me this favor, and you can have whatever you want.' smile. So like any other guy, I sighed then nodded my head.

A few moments later, I was sitting at the kitchen table as Hailey ran into the bedroom and returned with several makeup-thingies in her hands. She sat next to me, and used a pencil to draw on my lips, and then covered my lips in a kind of paint that I later learned was lip gloss. It took almost no time at all and she was finished. She made me wait, and then ran into the bedroom and similarly colored her lips. When she returned, I could see her cheeks were flushed and her eyes were in constant motion. She gets like this when aroused and I knew dinner would have to wait, it was obvious that we'd soon be having sex. She set her phone up and set the timer function on her camera app, and then smiled and our lips met, tongues twirling around each other and more photos that varied slightly. We browsed through the photos and honestly, they looked good. I know that it was me in the photos obviously, but it was easy enough to just imagine these were two strangers. I'm not homophobic at all but actually having the lip gloss on didn't exactly make me feel disgusted, but it wasn't something that I could imagine myself doing on my own.

Hailey took my hand and led me to bed, where the foreplay was brief before I sank into her body as our lips were joined. It started as a gentle, loving session, but had eventually escalated into raw fucking. Hailey has a few weaknesses, and I know that kissing her neck, and throat while having sex is a surefire way to make her orgasm. When I felt like I was getting close, my mouth traveled to her neck and I kissed her gently there, causing her to shiver in response. When I heard her telltale ragged breathing, I knew I'd only have to last a few moments longer before I could empty myself into her.

Afterward, we both laughed and snuggled. Each agreeing that we'd each just experienced powerful orgasms. When Hailey got up to clean up in the bathroom, she returned a minute later and looked ravenous.

"Oh my God Mark, you left this on my neck." She said pointing to the red lip print I'd inadvertently left there. It looked hot, I momentarily imagined a lesbian that had been kissing my wife's neck.

She sucked my soft dick into her mouth and seemed to be putting on a bit more of a slutty show of it. As much as I would have liked to simply get hard again so quickly, I'm not Superman and it takes a bit of time for me. So Hailey accepted it was too soon and instead busied herself sucking our combined juices from my dick.

Dinner that night was quickly forgotten. We had just returned home when she pulled me back to bed, and we fucked again. This time without me wearing any lip gloss. The sex was charged, and felt almost like I was fucking another person. When I came, I made a kind of grunting, roaring sound and that seemed to excite Hailey even more.

The next day, we did the normal Saturday stuff, grocery shopping, taking care of some things around the house, we fired up the grille and I cooked us steaks. As we sat on the patio eating, Hailey brought up the previous night.

"You know, I'm sure you do, but I just want to say that I don't think that lip gloss stuff last night means anything. I don't want a woman for a husband and I know you don't want to be a woman. I really enjoyed it though. I almost rubbed one out in the bathroom when I saw your lip gloss on my neck."

"You saw the picture, and it reminded you of us, the hair colors." I offered.

"Not till later, I just saw these two sexy people that were not bothered by labels you know? What did you think of how it felt having your lips made up?" She asked.

"It felt different from when we kissed and you had lipstick on. I can always sort of taste something, and it leaves a kind of residue behind on my lips. Last night was more intense than when I can taste or feel after kissing you." I described. "I think I was feeling whatever the residue typically is, multiplied by a hundred."

"Would you do it again? Not always but sometimes?" She asked with a mischievous grin.

"Maybe, so I recall someone saying they'd do anything I asked if I did that." I shot back with a grin of my own.

"I meant it Mark, tell me what you want from me." Her cheeks were flushed all over again.

I felt like it would be a shitty thing to ask for something that I either hadn't already done with Hailey, or to ask for something that I knew she wouldn't want (anal for example, we'd discussed it twice, and she flat-out explained that she wasn't interested and that it would hurt.)

"You give me everything I want, that's plenty." I said, and figured that was as good an answer as I could have hoped for.

Sex that night was wonderful, no there wasn't any return to the mutual lip gloss kissing, but I think we both were still riding that high from the night before.

The weekend faded into another week of work and I'll admit that I had spent several occasions recalling our 'photo shoot'. I may have dropped a hint that it was exciting during the week. That Friday after work, Hailey walked into the house and handed me her phone. The home screen was a cropped version of one of the photos we'd taken. Neither of us were recognizable as the photo was primarily just mouths, lips and tongues intertwined.

"I love that I know this is us, it gives me that same kind of nervous arousal as when we've had sex in the car, or in the park." She said.

"Send me that photo, I'll use it on my home screen too." I said with a wink.

"Mark, have you thought about us doing that again?" She asked.

After I nodded, she had my lips glossy and red minutes later. After more kissing like the week before when we ended up in the bedroom, I ate her to a squealing orgasm before I mounted her and came as deeply inside of her as I could.

The next day, without any influence on my part, Hailey locked herself in the bathroom, and when she emerged, she led us to bed. We kissed for a short time when her lips moved to my ear and she whispered "I want to feel you in my ass."

"What? Why? You said..." I stammered, the only guy in the history of guys that had always wanted to experience this with his wife and was now trying to talk her out of it.

"I have another favor to ask, but not till afterward." She said with a sly grin.

The first thought that came to my head was that she wanted to do something to MY ass, and that was going to be too much for me to agree with. We'd never needed lube and so we had none, but Hailey decided coconut oil would be safe and would work. I'll spare the details, but tell you that both of us were surprised at how things ended up, and afterward Hailey looked at me and said that she wanted us to do this more often. I imagined she meant the anal sex, but also mutual lip gloss stuff as well.

I could lie and tell you that concerned me, but on both accounts I'd be fine with repeat occurrences.

The following day, I found out what Hailey's next favor was, and it turned out to be something I enjoyed quite a bit. We'd eaten dinner, had watched a movie, and as the movie drew to its end we began touching and feeling each other. Hailey climbed into my lap and kissed me in this way that she sometimes does. It's difficult to explain but I'll try. Like many others, our kisses would start almost innocently, and then we'd have our tongues in each other's mouths. But Hailey had this way, our tongues would touch and then as our tongues danced, she'd almost slow down. I called it 'lazy tongue', she it wanted slow but impossible to ignore. Almost as if she was simply languishing in my mouth.

"Go under the sink in the bathroom and clean up for me, I'll be waiting in bed." She breathed into my open mouth. She rose and slowly swayed her hips as she walked to the bedroom while I watched her and decided that she wanted me to fuck her ass again, and that was fine with me.

I went into the bathroom, opened the cupboard under the sink and found the enema kit she had used the previous week. While I wasn't surprised, I was still not up for her putting anything in my butt.

I walked out and to the bedroom where I said "Hun, I'm not good with anything getting pushed into me, I'm sorry."

She shook her head, and then said "I promise, that's not what I want to do, I just want you to cum for me."

I looked confused, and she promised again, then said 'Pleeeeease?' Which, if I'm honest, is impossible to resist.

The enema wasn't fun, in fact it was uncomfortable, and I nearly had cramps. When I returned to the bedroom Hailey was waiting, naked and looking very aroused. I lay down next to her, and she immediately had her mouth on my dick. As her head slowly bobbed up and down, I felt her fingers circle the flesh of my scrotum, and she pulled my testicles away from my body slightly as her mouth did wonderful things to me. All too soon, she lifted her mouth and said.

"Roll over, on your hands and knees."

She got onto her knees, and faced away from me, but was against my side. I felt her hands on my ass cheeks, and then instantly they were being spread and I felt my wife's tongue dragging across the puckered flesh of my anus.

I let out a surprised gasp and then felt Hailey kissing me back there. One of her hands left my ass and circled my erection. She began stroking me slowly as she continued to lick me. Her tongue stiffened and she was trying to force it inside of me, but my body was having none of that and I'm sure I was clenched up tight enough to ensure nothing would ever breach me. She would lick and then as her tongue moved toward my scrotum, she stopped, and moved her tongue in a quick circular motion, lingering like that for a time before starting over.

I didn't realize that she was mimicking how a person might eat pussy, I just kept my eyes closed and enjoyed the sensations, eventually laying my head on the mattress and relaxing. She didn't try to force her tongue back into me, she didn't try to stick a finger into me, she seemed content to just pretend she was eating pussy. I'm not sure if I would have come without her fingers stroking me, but I certainly came and it felt fantastic. Afterward, I rolled over, and Hailey just watched me like a wolf may watch a sheep.

"Were you pretending to eat pussy?" I asked.

She nodded a bit "I've never been with a woman, I'm not sure I want to be with a woman either, it's just that we're still exploring and I've really gotten to like these new things we're trying. Can I ask a question that might be embarrassing to answer?"

"You just had your tongue on my asshole, I think it's safe to ask any question." I chuckled.

"Have you ever been curious about having a pussy?" she asked.

"Of course, all guys have been curious at some point I'd guess. I'd love to know what it feels like to orgasm as a woman. I'd love to know what it feels like to have a tongue on a clitoris. I'd love to know what a vagina feels like to have a dick inside it. But I think, even if it was all wildly better than what I feel right now, I know I'd always want to return to being a guy. I'd make a bad woman." I finished and then shook my head and laughed.

"You're just a tiny bit taller than me, and there's no way you weigh much more than I do, plus your natural blonde hair. If you had a pussy, handling the rest would be the easy part."

I'm sure she didn't mean it like I heard it, but I felt a bit insulted. No guy wants to hear that they could 'easily' become a woman.

The next few months cooled off a bit with the lip gloss, and rim jobs but Hailey regularly asked for anal sex and being a guy, I was happy to give it to her. One night as I was concentrating on not cumming inside her ass, she pulled herself forward on her knees enough to disconnect our bodies, then she rolled over and said she had another favor to ask.

I decided that if any of it put me in a situation that made me feel at all less than masculine, I'd tell her that I didn't want to do it. Instead, she got up, went to the bathroom, and returned a few minutes later, carrying a dildo, with a wired remote control.

"If we put this in my pussy, when you're in my ass, I think the vibrations will make both of us cum really hard." She said.

My dick fits happily on the upper range of 'average' and I like to believe I'm plenty thick enough, Hailey's pussy has always felt tight to me and she's never had difficulty in orgasming, but the dildo was both longer and thicker than my own equipment. I decided that I could either be a bit jealous of a piece of plastic or I could expand my sexual horizons.

Hailey was right, feeling the vibrations from the dildo in her pussy made us both cum violently. We began using the dildo, but noth every time. We used it enough that I always enjoyed it (especially the powerful sensations of feeling it moving in and out of her, with me being inside of her ass, there was the thinnest of barriers between the toy and me.) but not so much that I worried that she liked the dildo more than my dick.

One night, as I was fucking her ass, and she was switching between sucking the dildo, and then fucking her pussy with it, she fell forward, rolled over and looked at me saying "I want the toy in my ass, just promise to go really slow."

Naturally I'd wanted to see what that would feel like, I'd only ever been in her ass with the toy in her pussy. It took less effort than I imagined it would and that may have been due to the increased frequency of having me in her back there, but once the toy was fully seated in her ass, she swung a leg over my torso, and sank down on my pulsing erection. I knew immediately that I liked this better. When I came in her, the vibrations continued and the overstimulation nearly short-circuited my brain. My dick slipped out of her and I lay there gasping as she rested on top of me. My semen had leaked out of her and formed a puddle just below my navel. Hailey continued to slowly grind her body, still clearly enjoying the sensations the toy was proving to her ass. Her lips covered mine and she started her 'lazy tongue' action in my mouth. Everything was as perfect in the world as it could be.

"Honey, I hope you don't hate me, but can I ask for another favor?" She whispered.

There was no question in my mind, I knew exactly what she would ask for. I felt my body shiver for a moment, then I swallowed and nodded my head.