I (M30) and My Former Supervisor and Close Friend (F29) Reconnect and Ignite our Repressed Attraction [MF]

**Intro**

The early-2010s were hell on me, but it was worth it, because it led to this! This story takes place about five years ago. This is a long story, so settle in!

I had gotten married to my first wife, Maddie, right after we graduated college. She was the second woman I had dated in college, [Laura](https://www.reddit.com/r/gonewildstories/comments/kpzaio/the_cute_girl_in_history_class_mf_long/) being the first. Frankly, I should have seen the signs that it was going to be hell with Maddie. To make a long story short, we ended up getting married. By the end of the honeymoon, it was clear that I had made a mistake. For the next five years, I was in a loveless, and nearly sexless marriage with an unpleasable narcissist.

About a year after I graduated college, I finally got a full time job in my chosen field of work. The job didn’t pay very much and there was only limited upward mobility, so I was having trouble making ends meet. The administration of our agency were complete idiots who had the “if you don’t like how we do things, you can find another job,” mentality to morale boosting. The one thing that kept me sane in this job were some great co-workers, and my awesome direct supervisor, Christina. Christina’s smart, funny, kind, and really pretty. She’s about 5’7″, I’m guessing about 130 lbs, and has an excellent body. She has C-cup boobs, beautiful long, light brown/dirty blonde hair, and green eyes. Everybody in the agency loved her; she had a laid back, approachable, somewhat egalitarian leadership style. We listened to her because we genuinely respected and liked her, and she was going to do right by us. She did everything she could to make life happy at our workplace, though she knew it was a bit of a losing battle.

Christina and I got along especially well. Our personalities just clicked. Meetings over business matters that were supposed to take 15 minutes often turned into hour long chats about everything and anything. I admit, I found her very attractive, and I *thought* she might be attracted to me as well, as she sometimes seemed a little flirty. However, she was always friendly and warm with people, so I assumed that I was misinterpreting the flirtation. Even if it was flirtation, it was innocent. Christina was married and so was I, and neither of us are cheats.

I was happiest with my work colleagues, especially Christina. In terms of being supportive, Christina was everything Maddie wasn’t. I once told her about the troubles I was having with Maddie, but I felt guilty; I didn’t think I should be confiding intimate feelings with a woman who was not my wife, especially a woman I found attractive. But she got it out of me, was genuinely sympathetic, and suggested some counselors for Maddie and I. Maddie promptly refused.

After three years and living paycheck to paycheck, I got a better job offer with a state government agency. I was sad to leave, but Maddie was, for the first time, happy, as she would have more money. What sucked was that while Christina long understood my need to move on for better opportunities and encouraged me to do so (always emphasizing that she’d be sad to see me go, though) she acted hurt and distant when I gave her my two weeks notice. She wasn’t even in the office for me to say goodbye on my last day.

Unfortunately, the agency where I worked was miserable as all hell. It was like I was surrounded by Maddies. I slipped into depression, as I had unpleasable bosses at work, and an unpleasable boss at home. When I expressed my depression to Maddie, she told me to “quit bitching” because she couldn’t handle my bullshit. After a year, at the end of my probationary period, the agency decided I “was not what they were looking for” and let me go. When Maddie found out, that was the last straw. She had not loved me for awhile, and if I couldn’t even reliably provide for her, there was no use staying married.

Thanks to pre-nups and the fact that Maddie’s family was wealthier than mine, the divorce was relatively quick, and I kept the house and most of my stuff. However, for the next year, I was in near suicidal depression. Luckily, I was able to get another government job that paid as much as the bad one, and was a much more pleasant place to work. Also, with some medication and counseling, I started to recover.

I was doing well at my new job, and in the summer at the start of my second year, I got the opportunity to go to a weekend leadership conference up near Boston (I won’t bore everyone with the what and why details, but it was a good opportunity. Also, if you read the Katrina stories [Part 1](https://www.reddit.com/r/gonewildstories/comments/kny6qf/it_started_with_an_impromptu_lap_dance_f_it_ended/) [Part 2](https://www.reddit.com/r/gonewildstories/comments/kojpiv/it_started_with_an_impromptu_lap_dance_f_it_ended/), there’s something about me getting lucky at conferences). The day before I left, I noticed on Christina’s Facebook that she was asking people at her agency about carpooling to the same conference I was going to (though she was in the private sector, we were still in the same field of work). I messaged her and told her that I was going. She excitedly responded, “Hey! It’s so great to hear from you!! Give me a call when you get to Boston. We have to get together and catch up!” As it turned out, we were staying in the same hotel, so that made things even easier. Now, last time I knew her, she was happily married, and I didn’t bother to check her relationship status to see if that had changed, so my only intention was to meet up with my old manager and friend to have a drink and catch up.

**The Hotel Room Mishap**

On Friday night around 9 pm, I arrived at the hotel. As luck would have it, I was pulling into my parking space just as Christina was getting out of her co-worker’s car. She saw me and broke into a huge smile. At that point, I realized that I had forgotten how gorgeous she is. She looked great; she wore her hair down and she was dressed in a tight, formfitting white tank top and tight Capri pants.

I parked my car and quickly got and walked toward a very happy Christina. She threw her arms around me and squeezed tight, and returned the hug just as enthusiastically. She had on a sweet smelling perfume that, frankly, was somewhat arousing.

“It’s so great to see you! I’ve missed you *so* much!” she said.

“It’s great to see you too, Tina,” I said, “I was excited to see that you were going to this thing.”

She released me and we looked into each other’s eyes. I then turned to greet my other three former co-workers, Kelly, Michelle, and Diana, giving them all friendly hugs as well, though not nearly as intense as the one with Christina. They then all headed inside while Christina and I got our stuff out of the cars.

“You dropped off the radar after you left,” she said as we walked towards the hotel, “The only evidence you still existed was when you popped up on Facebook from time to time. Honestly, I was wondering what happened,” a twinge of worry in her voice.

“Ehh, I just had a really, really shitty two years. Taking that new job was a huge mistake. Thank God I’m not there anymore. I’m just getting over depression and stuff. Maddie and I got divorced too…a lot of shit.”

Christina gave me a sympathetic frown, “Aww, that’s terrible! I’m so sorry! I…haven’t been on social media much the past couple years…” she drew in a breath, “Remember how I was out of sorts the week you gave your notice? Well, it’s obviously not your fault, but that was the icing on the cake that week. I had just found out my husband, well, now ex-husband, had a side chick. So, yeah, shit’s been rough here too. But anyways,” she smiled again, “Let’s get checked in, and then we can go get a drink and talk about the good, the bad, and the ugly!”

I got checked in without a hitch, but according to the hotel front desk, there was no record of Christina ever booking a room…and there were no vacancies. They searched and searched to find out what went wrong, only to find that she *had* booked, but someone had fucked up and not entered it into the system properly and, right now, there was nothing that could be done.

“Could you room with one of the other three?” I asked.

Christina shook her head, “Kelly, Michelle, and Diana are staying together, and there’s only one bed in there from what I understand, so they’re bringing in a rollout already,” she shrugged, “I’d be on the floor. Plus, they were talking about staying up late and going to clubs and stuff, and I’ll want to sleep at some point tonight…which is why I didn’t just room with them in the first place,” she turned to the concierge, “You sure there’s nothing? Because I have no clue what I’m supposed to do right now!”

The concierge replied, “No, we are really, really sorry. Um…I can try and get you in at one of our other locations, but the closest one is about 40 minutes from here. I can do that and then if something opens up here tomorrow, we’ll get you right in.”

“You’ve gotta be fucking kidding me,” Christina mumbled. She looked about ready to cry. What I offered next was completely without any expectations whatsoever. Nonetheless, I felt nervous asking.

“Tina, uh…I don’t want this to come off wrong, but, I can see about getting a fold up bed brought to my room, and you can crash with me for the night until they get another room open,” I said, my stomach in knots. Christina was a good friend, and I really didn’t want to creep her out. I really only had the intention of helping her.

Almost without hesitation, Christina smiled and replied, “Really? You’re okay with that?”

“Yeah of course. I don’t want you to have to make a 40 minute drive…or sleep in the lobby!” I laughed.

She threw her arm around me and gave me a quick hug, “You are a lifesaver!”

**Catching Up**

We were told it might be awhile before they could get an bed to us, but that was alright, because we were planning on going to the hotel bar and grill and having a few drinks and appetizers. We went up to the room, dropped off our luggage, and headed back downstairs to the bar. But as we were walking in, Christina stopped short.

“Shit,” she mumbled, “Those two over there,” she gestured to a middle aged woman and an older man drinking cocktails, at a high top table, “CFO and one of the board members. If they see me, they’re gonna draw me in and want to talk business all night and I *really* wanted to hang out with you and not them!”

I nodded, “So what do you want to do?”

Christina thought for a second. “There’s a package store across the street. I could go pick up a couple good beers if want to order some appetizers to go from here. We’ll just chill in the room!”

I agreed and, quickly, before anyone saw her, she turned around and headed for the front door of the hotel. I went up to the bar and grabbed a menu. I ordered some fried mozzarella sticks and then took them back to the room, arriving at just about the same time as Christina, who had brought back two four packs of New England IPA from some local microbrewery. We got into the room and Christina told me she was going to change into pajama pants. I asked if she wanted me to go into the bathroom or turn around.

“Um,” she smiled and laughed nervously, “I don’t really care. I guess don’t like…stare at me and lick your lips and we’ll be okay.”

I laughed, “Okay, well, I guess I’ll change into gym shorts or something if you don’t mind.”

I opened my suitcase and grabbed a pair of shorts, then stood up and took off the khaki cargo shorts I was wearing. I caught a glance of Christina from the side as she was bending down to pull up her pajama pants. I noticed she was wearing tight, blue panties; nothing super sexy like a thong or anything lacy, but definitely not granny panties. I quickly looked down, telling myself *Don’t get a boner, don’t get a boner…* and my dick was like “Fuck you! You just saw your hot former boss in her underwear! Don’t tell me what to do!” Anyway, I tucked my hardening dong under my waistband and sat down on the bed, positioning my legs to not make my arousal obvious. Christina crawled up onto the bed next to me and handed me a can of beer, which I cracked open. Hiding my excitement got even harder (haha) when I noticed that she had also clearly removed her bra from under her shirt. We toasted with our cans making a dull ‘clunk’ and began our feast of junk food.

I told Christina about how I was miserable with Maddie, how my previous job was shit, and how I missed working with her. Christina told me about how she was blindsided by her husband; she thought they were happy, until she saw the signs (him being possessive with his phone, not keeping his story straight about where he went, etc.). Also, during this time, she had gotten pregnant, but had a miscarriage early on. She knew something was up when her husband actually had the audacity to say that he was relieved as he had been thinking he no longer wanted kids. When she finally confronted him, he admitted that he had been seeing his mistress off and on since before he and Christina were married. He had begged her to stay and give him time to decide who he wanted. When she told him to end it and decide immediately, he called her “selfish,” and that was it for the marriage. He begged over and over during the divorce, but Christina had too much self-respect. She let him have the house and all his toys and she moved into an apartment not far from where I lived.

**This is Where the Fun Begins**

Christina and I finished up the beer and cheese sticks, then took turns in the bathroom (Double IPAs make you have to pee) and brushing our teeth. By this time, the fold out bed still hadn’t come, so we sat down again next to each other. There was a moment of silence, and then Christina inhaled sharply and exhaled.

“You alright, Tina?” I asked.

“Um,” she bit her bottom lip and gave an awkward smile as she stared ahead, “I, uh…Oh, gosh, I don’t want to make this weird…”

I felt a jolt of either excitement or anxiety run through me…I wasn’t sure which. Either good news or bad news was coming.

“I just have to get this off my chest,” she said, “When we worked together, I felt really close to you. Like we just…clicked, you know? And even when I didn’t know about Tom cheating, or Maddie treating you like she did I…sometimes wondered what it would be like if you and I were together. I felt bad, because I was like I love my husband and wouldn’t leave him, but, I was attracted to you. I wasn’t going to act on it, but I had to admit that I was.”

My heart was pounding through my chest. I looked over at the beautiful woman sitting next to me, who had just confessed her crush on me. She looked really nervous, but she kept talking.

“And when I found out about Tom, I was laying in bed that night thinking maybe tomorrow you would tell me that Maddie had left you, and…I know it sounds awful to think that, but it was a weird thing and I wasn’t thinking straight. Especially because of the whole agency policy of supervisors not dating subordinates,” she forced a laugh, “But it was like, you were rejecting me too. Which is stupid because it had nothing to do with anything personal. But…yeah. I just had to get off my chest that I had feelings for you.”

I can be socially awkward, but I’m not *that* dense. Also, Christina’s confession made me realize that my attraction to her was not just physical, and my feelings for her were not platonic. So, I went for it.

“Christina…uh, well, I felt the same way. I mean, I can’t tell you how many times I imagined…*us,*” I laughed, “You know, the whole thing where you feel too guilty to fantasize about cheating, or about our spouses dying or leaving us…I’d imagine us meeting before we met our spouses and then say, ‘oh well, if life had been different, who knows? But she’s married, and she’s my boss, so…oh well.’ So, yeah, I felt the *exact* same way.”

We turned towards each other and looked each other in the eyes. Christina’s turquoise eyes were sparkling like gems. She was breathing heavily, and she was doing everything she could to appear composed, holding back a huge smile. *God, not only is she objectively gorgeous,* I thought, *she’s my type.* I already knew that, though. If you were to ask me to describe the type of woman I wanted to be with, I’d give you both the looks and personality of Christina. The best part was, we had no illusions about each other; we had seen each other’s bad side, argued, hurt each other, and made up. And we both had quirks and flaws that got on each other’s nerves and would need to work on…just like a good couple. I knew we were right for each other.

“And now here we are,” I continued, “Single, not manager and employee. I guess this is our ‘other time, other place.’ So, I guess, I just want to ask, you said you *had* feelings. Umm…do you still have those feelings?”

She suddenly exhaled and threw herself towards me, our mouths meeting in a passionate kiss. Our tongues tangled together as I threw my arms around her and she crawled onto to my lap and straddled me. She broke the kiss for a moment and said breathlessly, “You have no idea how long I’ve wanted to do that.” before we went back to making out.

My cock went from half chub to full mast in under a second as we continued to kiss and caress each other. Christina began to grind herself against my knee; I could feel that she was already soaked. She began to grind harder, her breaths becoming gasps. I reached my hand down into her panties and caressed her ass, moving my hand to the outside along her hip, and down the front. She was shaved but a bit prickly, like it had been a day or so. Her pussy was a hot, sticky swamp. She gasped and pulled away from our kiss as I slipped a finger inside her and rubbed her G-spot, my thumb rubbing her clit. Her eyes rolled back in her head as she arched back and sat up. She then looked me straight in the eye, an ecstatic on her face as she pulled the straps of her tanktop off her shoulders and pulled down her shirt, revealing the most perfect breasts I’ve ever seen! They were big, but not massive (again, C-cup), and her nipples were a perfect size, not super dark but also not pale.

“Jeez, Teen,” I said, “If you had an OnlyFans, you’d have a hundred thousand followers with those things!”

Christina laughed as she pulled her shirt over her head and threw it on the floor. I pulled off my shirt as well and sat up to caress her boobs and suck her nipples, all the while still playing with her down below. Christina closed her eyes and moaned as I licked her nips, caressing the back of my head and neck.

After about a minute, it was like Christina suddenly kicked into another gear; she began to hyperventilate, then screamed out loud and shuddered uncontrollably as she came. Catching her breath, she kissed me deeply, then kissed my neck, and made her way down to my shorts, pulling them down and springing my cock free.

“Wow,” she said with a smile as she grabbed it, “Not bad *at all*!” (I’m not huge, but a little bigger than average, between 6.5 and 7 inches). She then hungrily began blowing me. She was pretty damn good. Not like she gave blowjobs out like candy in high school and perfected the art (which was definitely not her). She just knew what to do. Now, if not for the fact that I was in the midst of tapering off antidepressants which delay my ability to cum, I probably wouldn’t have lasted more than 30 seconds. However, I was honestly just getting started (Thanks, Luvox). Even then, I didn’t know how long I would hold out once we actually started having sex. I didn’t have long to find out though.

Christina suddenly stopped the blowjob and asked, “Sorry, but…I really want you right now. Can we do it?”

I nodded, and she quickly pulled off her pants and underwear and spread her legs. Her vagina was pale pink with a large labia, though not exactly “beef curtains.” Honestly, it was how I fantasized she would look! I climbed on top of her bent down to kiss her, entering her as I did. She was so wet it was like she had squirted an entire bottle of silicone lube into her vag (another time later, I joked that we should sell her juice as a lube, which earned me a playful slap on the arm and a mock reprimand that I’m disgusting). She drew in a deep breath through her nose as I penetrated, throwing her arms around my neck and pulling me even closer.

“You okay?” I asked.

“Better than I’ve been in years,” she whispered before she kissed me again.

We sensuously made love for about five minutes. At her request, I thrust hard but at a slow pace as I kissed her mouth and neck. I needed to control my pace or I wasn’t going to last long, but I wanted to go harder, and I was sensing that she did as well. I repositioned so that we were at a better angle, and I could get better penetration. I began to pull out further and thrust harder. As I started this, Christina’s eyes rolled back into her heard and she made a sound like “GUULLG!” I stopped.

“Are you…”

“Shut up and keep doing that…hard!” she groaned. Immediately, I resumed, humping her even harder, the sound of our thighs slapping filling the room with each thrust. With each thrust, Christina spasmed and made that same choking sound. I gradually quickened my pace over the next few minutes, which caused Christina to go from “Gulgs” to gasps. I then sped up to as fast as I could go in this position and, after another half a minute, I felt her pussy clench around my dick as she let out a scream. Though she was even tighter now, her orgasm released even more lube, which made the humping just as easy, but even more pleasurable. I felt my own cum approaching. I felt a little embarrassed as it had only been about seven or eight minutes.

“It’s been awhile, so I’m not to last much longer,” I breathed out.

“I don’t care,” she gasped, “this is just the first time, I’m…about…to cum again…anyway!”

I sat up straight and jackhammered her hard. The sudden quick pace sent her over the edge into another orgasm. The fast thrusting, the sight of my penis thrusting in and out of her vagina, and her tightening from cumming did it for me. My cock and balls tightened and tingled as I shot what felt like a gallon of cum inside Christina. Like a fully automatic rifle, my dick reloaded and fired another huge shot. Over and over I unloaded years of cum I hadn’t even known I had set aside for Christina.

As I bent over and caught my breath, Christina opened her eyes and smiled, then threw her arms around my neck and pulled me down into a passionate kiss. Our lips and tongues danced for about twenty seconds before she broke the kiss and said, “To answer your question,” she smiled and looked up and away, pretending to contemplate her answer, “Um…yeah, I think I have some strong feelings for you. How about you?”

I kissed her again, then replied, “Yeah. I think I might be still be somewhat attracted to you as well.” She giggled. I pulled out and crawled off of her, unfortunately leaving a sizeable puddle of jizz on the sheets. Christina rolled her eyes; one thing about her, she’s squeamish.

“I’ll grab some wet paper towels, but that’s *your* fault, so you get the side with the wet spot!” she teased as she got up. I smiled, shook my head, and rolled my eyes.

We both got cleaned up and dressed for bed (neither of us like sleeping naked). My heart wanted me to stay up and have sex as many times as my body would allow, but the emotional rush had drained both of us, and we were going to meet the other three women for breakfast at seven the next morning before the conference started, and it was already after 11. I know, we weren’t kids anymore.

Christina crawled under the covers with me and turned out the light. I was already half asleep as she snuggled in close to me. I pulled her in close and we kissed goodnight.

So, what became of Christina and I? Did we wake up the next morning and decide it was a mistake? Or did it last for the rest of the weekend? What do you think? Take your guesses, and find out when I post part 2!

Source: reddit.com/r/gonewildstories/comments/mib7ev/i_m30_and_my_former_supervisor_and_close_friend