Milking a Trip to Miami

Please note: this story, which is a long one, mostly focuses on two coworkers and the relationship that develops between them, but includes lactation play, anal, and a threesome. If that's not what you're looking for, you might want to skip this one.

"I'm sorry, Jay - there's just really no other option. The hotel is filled up with our staff and attendees and with several city-wide conventions underway across Miami, there's no other hotel with a room available within miles."

Linda, my boss, explained all of this with the air of someone who had been more than happy to book herself in to arrive a few days early and didn't have to share her room with a coworker. Or that might have been me projecting just a bit. Or it might've been the fact I'd asked to come out a day earlier but was denied because of the "cost." Either way, it was the end of a long day of travel and I just wanted to get to my room, order room service, veg out for a bit, and then hit the sack early since I'd be up at the crack of dawn to start preparing for my company's conference.

I sighed. "Okay, but any idea who I'll be sharing with?" I've worked at this company for more than a decade and while I liked many of my colleagues, I liked them as coworkers, not roomies. Linda paused as she thought for a second, "Well, almost everyone is here and I'll need to take a look at the rooming list, but there's only a handful of folks who are still expected. It will definitely be someone else from staff and not an attendee if that helps."

It didn't help, but Linda went on to explain it would only need to be for two nights and then the hotel would be able to move either myself or my future roommate to a different room. I sighed again. Well, it could certainly be worse, I suppose. I replied, "Okay, Linda. I guess I'll try and make the best of it."

"I knew I could count on you, Jay!", Linda enthused. "And as a thank you, if you'd like, after the meeting is over I can give you a couple extra days of vacation once we're all back at the office. Just let me know by Thursday." I thanked her and made my way to the reception desk to check-in and pick up my keys.

~~~

"Mr. O'Neill?" The desk clerk was looking at me expectantly. I must have completely zoned out. I tried to look suitably abashed and replied, "So sorry, I spaced out there for a second -- it's been a long day." Victoria, according to her name badge, smiled with what seemed real sympathy. "Quite all right, sir. I was just asking if the offered room would be acceptable. I understand you're having to share with one of your coworkers." I paused, and replied "Would it hurt your feelings terribly if I told you I lost the thread a bit before that? I must be even more tired than I thought."

Victoria's eyes crinkled up with the smile this time. "Of course, no problem. I was just saying the last double queen room was booked but that I do have a room that's not part of the current official inventory - it was in the process of being remodeled and it hasn't been added back into the system yet. It's a suite with two cozy, but separate bedrooms -- however only one of the two guest bathrooms is in working order, though there is a powder room off the suite itself. If you think you and your colleague would be fine with that, I think it might at least provide some privacy. And I'll be also providing you some vouchers for some additional amenities during your stay to make up for the inconvenience."

"Victoria, if I wasn't already married, I think I might propose here and now. Yes, that would be perfect. I really can't thank you enough." She gave me a little wink and quietly added, "We'll just have to see about that, won't we?" And then a little more loudly, she went on "Here are your room keys, Mr. O'Neill. Room 1749. That's here in the south tower, and the elevators are just here to your right. Do you need any additional assistance or is there anything else I can do for you?" She looked at me with an open and frank look. I took in her curly auburn hair and freckles -- one of my favorite things. It really had been a hell of a day and while the spirit was willing, the flesh was weak.

"Any other night, Victoria, and I might consider taking you up on that, but I think I'm about done in for tonight. Will you be here again tomorrow?" I asked. "Yes, I'm working nights for the rest of the week. If I can be of any service to you or if you need anything, please just let me know," she paused, and licked her lips. "Anything at all."

~~~

A few minutes later, up in my room but lighter by a pair of shoes and starting to shake-off the weight of the day, I paused to take stock of my surroundings. The suite was the type often used for corporate entertaining, with two small bedrooms off a main shared room. My bedroom was on the left, as you entered the room -- as I was first here, I went ahead and took the bedroom with the working bathroom. The other one was almost done, but the sink and toilet installation wasn't completed yet. Whoever my roomie was, they would have to either make do with the powder room attached to the central shared space or ask to borrow my shower. Considering the view from the main room, I doubt they'd complain. The windows looked out on the bright lights of the city and the open water. I was happy not to be on the other side of the hotel with the view of the pool -- I doubt it would be a problem seventeen floors up, but in my experience, hotel pool areas are not conducive to sleep.

My phone rang, it was my wife Marie. "Hey Sweetie. You hire a new pool boy yet?" I asked.

"You know, no one else is willing to work as hard as you do for so little pay."

"I stay in the job for the fringe benefits."

We bantered back and forth some more, talked about the kids, and were wrapping up our conversation.

"So you find any sweet young thing down there in Miami to help you deal with the crushing loneliness of life without me for a few days?"

"Well, there was a really cute desk clerk who was giving me the eye. You'd like her - she's just our type."

"Ooh, do tell!"

Marie and I had a number of encounters with other couples and women over the years, though less now than we used to. We both enjoyed our sexuality and had no shame about expressing it. I was a straightlaced boy before I met her, but she opened up my world and my mind in the process.

"You know... young, drop dead beautiful, flirtatious, and curves in all the right places."

"Well, she sounds delightful. Probably not a brain in her head, but she sounds like a tasty morsel. It's been awhile since we had some fun like that. I'll tell you what, if you get a chance to have a little escapade this trip, why don't you go ahead. If you're going to be stuck in Miami, you might as well milk it for all it's worth. Then come home and tell me all about it... while you fuck my brains out."

"Well, if you insist," I said while laughing. We talked a bit more, but she had to go check that the kids were actually down and told me she'd call me later in the week.

I sat down on the couch to look out at the view... and then went blank for a bit. I'm not sure I wasn't actually asleep, but as soon as I heard the door to the room open, I blinked myself awake and started to stand up. Hmm, judging by how hard that was, I probably was asleep. My musings were quickly dissipated by the sight of Gwen, one of my friends from work, coming in the door.

"Jay! What are you doing here?!" she asked, not with any real upset, but just curious. "Sorry! Didn't they tell you downstairs that you'd have a roomie for a couple days?", I explained, and then added, " I figured they'd match me up with one of the guys from the office. Let me go down and see if I can straighten this out."

She gave me the smile that was one of the reasons I truly enjoyed her company and said, "Oh, don't worry about it! It's late and the girl down at the desk was quite clear this was the only room available. Honestly, I'm fine with this if you are - I was worried I'd be stuck with someone I couldn't stand." She went on, " We're both adults and it looks like we have our own rooms. At this point, I just need to get settled in and try and de-stress enough to get to sleep. And... oh, shit!" She looked down at her blouse, where a dark circle had formed in the fabric around each of her nipples. "Damn it! This is so embarrassing - my flight was delayed and I haven't been able to pump for hours. Will you excuse me? Oh, wait - which room is mine?" I pointed and she grabbed her suitcase and headed quickly into her room, shutting the door behind her.

~~~

Gwen and I had become friends pretty much since she first started at our company two years ago. It wasn't really anything beyond the sort of friendship that just sort of clicks when two people find they can talk easily with each other. Everything professional and above board, but an honest human connection nonetheless. She had been out on maternity leave with her first child earlier in the year and had just been back in the office for a couple months before this conference. And as evidenced by her shirt, she obviously was still breastfeeding her new son. The fact we were both parents and the tribulations and joys involved in that were some of the many things we had bonded over. I had genuinely missed her company while she'd been out, and while we'd stayed in touch while she was on leave, I'd been surprised by how much I enjoyed her being back in the office. She was just one of those people who made any situation better.

And to be honest, she came back from maternity leave looking amazing. She'd always been cute, but with her hectic schedule, she had lost the baby weight and then some (while somehow keeping some really nice curves) -- and despite the stress of a new baby and a husband that wasn't all that helpful, she seemed happy and had a bit of a glow about her.

~~~

I was still standing there, just sort of spacing out and looking out the window when I heard her call my name. As I started walking towards her door, she opened it up and looked to nearly be in tears. "Jay, can you... can you please help me? I think the TSA must've dropped it or something, but my pump isn't working...and after several hours of travel, I'm... well, I'm very uncomfortable. Sorry, probably too much information, but I...well, I just don't know what else to do."

"Sure, no problem!" I went into her room and walked to the bedside table where the breast pump was sitting. It was the same model my wife had used, so at least I was familiar with it. Between my personal experience with the ones my wife used with our two kids and a past career in IT, I started walking through the troubleshooting steps that made sense. "Hmm...power cable, check." I tried it in a different outlet with no success. "Do you have the battery pack unit as well?", I asked. Gwen pulled it out of her bag and handed it to me. I tried that but still no luck. I fiddled with some of the other bits as well, but nothing was working with any of it.

"Gwen, I'm so sorry - it seems pretty dead. I know the motors can sometimes fail on these, but this looks like a fairly new model but it's the only thing I can think of."

"Oh...what... Jay, I literally don't know what to do! It's only a pump-and-dump, but..." she cradled her arms around her sizable breasts,"these really hurt!" She sat down on the bed and started to cry. I sat down next to her and put my arm around her shoulders to try and comfort her. As I did, I felt her just sort of relax into me.

"Jay? I know this probably goes beyond all bounds of friendship but I really need some help. I'm not going to be able to pick up a new pump until sometime tomorrow and...well, do you think you could bring yourself to help me out?" She looked up into my eyes with real pain and no small amount of apprehension in her eyes. "I mean, I completely understand if you don't think you can, but you have really always been there for me and I can't think of anyone I could trust with this more than you."

I looked into her eyes and smiled, "Gwen, of course. I completely understand. Just tell me how you'd like to handle this."

She looked at me, relieved and pensive at the same time. "Oh, thank you so much! I don't even know how to thank you. But my other problem is I don't quite know what to do either. I mean, I can express the milk by hand, but that takes forever and can be really painful - especially with as full as they are now."

I paused for a second, thinking. "Well, since we sort of seem to have gone through the looking glass here, and you are extending no small amount of trust to me, I suppose I can't do any less. My wife ran into similar problems when she was breastfeeding our kids, and I helped her then. I think I know a few tricks that might help." Gwen looked back to me with gratitude in her eyes. I continued, "This may seem to be sort of unconventional, but if you can trust me, I think I can help you. We may have to cross a few boundaries of what's considered normal, but I promise I'll do everything I can to not make you uncomfortable."

She kissed me on my cheek and said, "Thank you, thank you, thank you! Yes, whatever you say - honestly, I can't imagine you ever making me feel uncomfortable. What do you need me to do?"

"Follow me, and I'll show you." I stood up and held her hand and led her into the bathroom attached to my bedroom. I reached in and turned on the shower and said, "I appreciate how much trust you're showing in me, so I will try to do the same for you and we'll keep this in a safe zone. I'll strip down to my boxers and if you can strip down to your bra and panties -- or a swimsuit if you have one with you?" She answered, "No, I didn't bring one this time - with the meeting and feeling a little nervous about my body after the baby, I skipped it this time." I chuckled, "Gwen, I don't know if you'll believe me or not, but trust me - you have nothing to be nervous about with regards to your body. Not at all. You always look amazing, and since the pregnancy, that's been even more true. Now, if you're ready, we'll head into the shower, okay?" She nodded, looking a little apprehensive but also still very hopeful for any sort of relief. I turned around to... hell, I don't know why I turned around, but it seemed the right thing to do. Once our backs were to each other, we proceeded to take off our clothes, leaving our underwear on. We turned back around at almost the exact same time.

Gwen looked at me and smiled "Well, this is a little awkward, but I really have to say, I couldn't imagine anyone better to be here helping me. So what's next?"

"Let's step into the shower and I'll show you." While the bedroom was small, the bathroom was actually a decent size and contained a separate tub and shower, with the shower being glassed in with a door. I opened the shower door again and gestured for her to enter. I followed her in and closed the door behind us. The water had warmed up and after my own day of travel, it felt quite nice.

"Okay, I need you to turn towards the spray and take off your bra." As she turned away from me and unsnapped her bra and removed it, I took it from her and tossed it back out of the shower. I stepped up right behind her, almost but not quite touching. "Now step up until the spray is hitting as much of your chest..."

"Jay, I think under the circumstances you can say 'boobs'."

I laughed, and went on instructing her "...as much of your boobs as possible." She scooted forward a bit and let out a happy sigh as the warmth from the water started relaxing the muscles and tissues in her breasts.

"Oh, that feels so good! But is this really going to help long-term?"

"That was step 1. This is step 2." From behind her, I moved closer and reached around to her chest. I placed my warm, wet hands on her breasts and very gently started massaging them, focusing on sliding my hands across her breasts rather than trying to use my fingers or really squeeze them. Her head tilted down towards mine and she let out a big breath. I continued, "step 3 is a little more intense, but I have to ask one more time: are you sure you're okay with this? If at any point, you want me to stop, just say so, okay?"

"Jay, my boobs are in your hands, and I've already shared pretty much every embarrassing story about my life - it's not like we have many secrets from each other. Hell, you know the ins and outs of my life better than almost... no, strike that, you absolutely do know my life better than anyone. I trust you and know that whatever you do, you'll do whatever you can and as you always do, you'll make me feel better." She winced slightly. "And speaking of which, the heat was nice and the massage is heavenly, but there seems to be more pressure now."

"Yeah, the heat and gentle massage is a good way to relax the tissues, but that tends to lead to more milk letting down. And thank you, that means a lot to me. Again, if you want me to stop, just..."

"I got it, Jay. Just go ahead. Please."

I turned her sideways and moved in front of her so the spray was hitting both of us. My hands moved back to gently cradle her right breast, where despite the spray from the shower, I could see milk seeping around her nipple and dripping down. I bent down and slowly wrapped my lips around her areola and nipple and started to suck. She gasped in a breath and then let it all out in a deep, guttural sigh.

As her milk filled my mouth, she said, "Oh, that feels so much better. Please, please, don't stop." Her milk continued to fill my mouth as my suction on her breast continued. I realized I hadn't asked her an important question and now I literally couldn't. I pulled back and looked into her eyes, hoping against hope she understood what I needed to ask without words. She looked at me for a moment, and took in my mouth full of milk and laughed. "Oh, yes - please, go ahead and swallow or spit it out. Whichever you prefer." Still looking her in the eyes, I let the sweet liquid in my mouth go down my throat and swallowed. She gave a slight but noticeable shiver upon seeing me swallow her milk.

Her hand snaked up behind my head and pulled me towards her breast. "You silly, wonderful man. Thank you for thinking of me and trying to be aware of my limits, but right now I just need more of that." I returned to her breast and once again latched on to her breast, feeling the milk flow freely - warm, and sweet, swallowing as I went along. This was something my wife and I had done more than a few times, and it never failed to make both of us horny as hell. But I was still trying to be good. Dammit.

After a few more minutes, she pulled my head back and pushed me towards her other breast, where once again I latched on, sucking down her sweet juice -- all the while listening to her happy sighs and occasional moans. In fact, as I went on, the moans became more and more frequent.

Finally, after a few more minutes, the flow of milk had decreased to a small trickle and then finally, nothing at all. However, I couldn't bear to let that perfect breast out of my mouth and her other hand came up to the back of my head, keeping me right where I was.

Thank god for hotel showers with huge amounts of hot water. The glass walls of the shower had completely fogged up and it seemed like we were in our own little world. With all the steam in the air, it took me a moment, but I noticed the smell of her arousal all around us. I took a chance and lightly flicked my tongue across her nipple and then circled it a few times, and then went back to lightly sucking on that glorious flesh, but more sensually. She shuddered in response, her back arching and her hands and arms holding me tighter. I pulled back from her breast and we just looked at each other, grinning like complete idiots. Gwen laughed and threw her arms around me, resting her head on my chest.