New Here - We started to explore

[Greg_N_Shelley]

It sounds like you and Tim have a great mindset and are off to a good start.

I'm curious, did Jake seem to catch any subtext when Tim described your relationship? Many of us here would pick up on "open communication and trying new things together", but guys who haven't been exposed to open relationships may be less inclined to read between the lines.

[rascalnvixen]

Ash, I'm following your thread with great interest. You express some similar thoughts we had when we first became involved with the alternative lifestyles. I do have one question for you, how many men have you have had sex (intercourse) with?? It is interesting reading of your excitement with possibly having sex with another man other than your BF.

Rascal

back in high school, I had my share of fun; I’d say I was with a handful of guys during those years—six, if I’m counting right. Maybe even coming off a bit wild or “slutty” in the best way.

Junior year, there was this guy, Matt, on the soccer team - At a beach party we slipped away from the crowd, found a quiet spot, It was raw and quick.

Senior year, I dated Chris for a few months, and we’d get wild at house parties. One night, after too many drinks, we ended up in an upstairs bedroom. He pinned me against the wall, and it went from making out to full-on action on someone’s guest bed.

Late in senior year, I went to a big party at a friend’s lake house. I was tipsy, maybe a bit more than tipsy, from too much cheap vodka. Two guys I knew from school, Alex and Nate, were flirting hard with me all night. We ended up in a bedroom, it started with some playful kissing - one thing led to another. Nate pulled my top off, before I knew it, my skirt was hiked up and Alex was fucking me from behind .They took turns, flipping me between them, it was chaotic and messy.

There was this guy, Jack who I’d flirt with after school. One evening, we parked his car by a lookout point, started making out, and things escalated fast. We climbed into the backseat.

After high school, though, I settled down a lot, focusing on college and my career, and didn’t date much

Thanks for the reply, Ash!! Your reply was what I was expecting. It seems you enjoy the experience of flirting and then taking it further to completion. I think you like having new men's bodies to explore and have sex with. I think being more focused on career and bf has not allowed you the freedom to experience new cocks as you did in HS. This is a great way to enjoy the thrill of new cocks and new lovers to see how they differ. Looking forward to more of your story!!!!!

Rascal

[ash_hotgf]

So, Friday night, I had a work event at hotel downtown for a big marketing campaign launch my team’s been working on. One of our key clients, David, was there, late-30s exec. During the event, I was working the room, chatting up various clients, when David approached me at the bar. We got to talking, just the two of us by the bar, about the campaign, his company’s goals, and then it went personal. He asked about my weekend plans, and I mentioned grabbing drinks with Tim and a friend. His hand brushed mine as he handed me a drink, lingering just long enough to make my pulse race. He kept the flirty vibe going, complimenting my dress. I laughed, keeping it light but feeling that familiar rush from the club night. Nothing physical happened. He dropped lines like I’d love to hear more about your adventures sometime and even teased maybe I’ll crash one of your drink nights. It was all playful. We chatted for maybe 20 minutes before I rejoined my team.

David gave me his card as we parted, saying let’s grab coffee to talk shop or whatever else comes up. I’m pretty sure “whatever else” wasn’t about marketing. As soon as I got home, I spilled every detail to Tim over a glass of wine. I told him how David's flirty comments and that hand brush got my heart racing, and how it felt. Tim was all over it and he said fuck, that’s hot you flirting with a client like that and I’m so into it. We laughed about how unexpected it was, and it turned into fuck night for us. There’s a professional line we’re careful not to cross too far, but the idea of flirting in a work setting is a turn-on we hadn’t explored yet

We’re not sure if David's a real contender like Jake, but this moment opened our eyes to how the lifestyle can pop up in surprising ways

[jane]

in my experience's we're as likely to find someone in the wild as online. there are lots of willing people online, but they don't always follow through, or they're skeevy.

[Greg_N_Shelley]

in my experience's we're as likely to find someone in the wild as online. there are lots of willing people online, but they don't always follow through, or they're skeevy.

I agree, but I think a lot depends on the woman and environmental opportunity. My girl had several men approach her over the years, but was always too shy to respond regardless of my encouragement. We had best success with online situations where intention was already established with only two disappointments (one no show and one “weak performer”). Maybe we were lucky or did our diligence well, but most of the guys we met online were great.

Now for self-confident and vivacious women like yourself and Ash, I agree. The world is full of natural opportunity.

[sandy691196]

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[sandy691196]

So, Friday night, I had a work event at hotel downtown for a big marketing campaign launch my team’s been working on. One of our key clients, David, was there, late-30s exec. During the event, I was working the room, chatting up various clients, when David approached me at the bar. We got to talking, just the two of us by the bar, about the campaign, his company’s goals, and then it went personal. He asked about my weekend plans, and I mentioned grabbing drinks with Tim and a friend. His hand brushed mine as he handed me a drink, lingering just long enough to make my pulse race. He kept the flirty vibe going, complimenting my dress. I laughed, keeping it light but feeling that familiar rush from the club night. Nothing physical happened. He dropped lines like I’d love to hear more about your adventures sometime and even teased maybe I’ll crash one of your drink nights. It was all playful. We chatted for maybe 20 minutes before I rejoined my team.

David gave me his card as we parted, saying let’s grab coffee to talk shop or whatever else comes up. I’m pretty sure “whatever else” wasn’t about marketing. As soon as I got home, I spilled every detail to Tim over a glass of wine. I told him how David's flirty comments and that hand brush got my heart racing, and how it felt. Tim was all over it and he said fuck, that’s hot you flirting with a client like that and I’m so into it. We laughed about how unexpected it was, and it turned into fuck night for us. There’s a professional line we’re careful not to cross too far, but the idea of flirting in a work setting is a turn-on we hadn’t explored yet

We’re not sure if David's a real contender like Jake, but this moment opened our eyes to how the lifestyle can pop up in surprising ways

The way you paint the pic, this David guy, late 30s, probably married or attached, a client side guy, is a good catch to break you in as a hot gf.
He has a lot to lose by babbling or boasting about his "conquest". He knows you have a BF and this will probably play out as "cheating". Most probably a short fling.

I see this as a high excitement, low risk initiation to the real thing.. the LS.

Cheers.

[ferrisandrews]

in my experience's we're as likely to find someone in the wild as online. there are lots of willing people online, but they don't always follow through, or they're skeevy.

Where would you say your top 2 or 3 places in the wild are that often deliver someone worthy?

[ash_hotgf]

Morning forum
We invited Jake for drinks at downtown bar - think neon lights, music and atmosphere that screams sexy but chill. Tim picked the bar - great cocktails and dark corners . I wore a tight black mini-dress, low-cut with a slit up the thigh, paired with strappy heels to make Tim and Jake’s jaws drop, Tim looked hot in fitted jeans. Tim was fucking pumped - I want to see you let loose, babe. I was a mix of nerves and anticipation.

Jake rolled in at 9 PM, looking great in dark jeans, fitted gray shirt and that killer smile. He spotted us at a corner booth, greeted Tim with a bro-handshake, and pulled me into a hug followed by whisper "You’re killing it in that dress". We ordered drinks mojito for me, whiskey for Tim, bourbon for Jake and we dove into easy chat. Jake shared a hilarious story about a surf trip.

An hour in, the air got thick. Jake leaned closer over the table, saying that dress is fucking criminal and I was making him hard to behave. I just said good thing Tim’s here to keep us in check. Tim couldn't help but say "or to enjoy the show". Jake raised an eyebrow, sipping his drink. We played a flirty game of Two Truths and a Lie - I’ve never kissed a stranger, I love being watched, and I hate spicy food. Jake called my bluff on the kissing. I laughed, admitting it was the food lie, Tim chimed in " she loves being watched".

We moved to a quieter corner of the bar, the three of us jumped into a booth, me between them. Jake’s thigh pressed against mine, I let my hand scratch his arm and Tim’s hand was on my other thigh. Jake’s touches got bolder - his hand on my lower back.

With Jake we went for slow number, he invited me on the floor and Tim just nodded. We slid out of the booth, Jake’s hand on my waist, and moved to a dark corner of the dancefloor - my tits against his chest, his hands low on my hips. I swayed, letting my dress ride up slightly - he said I'm killing him. I whispered back - Show me and that was it—his lips into mine. The make out was heavy, like 15 minutes. His hands were on my waist, then my ass, squeezing just enough to make me gasp into his mouth. I sucked his tongue, feeling his cock through his jeans. Tim watched from the booth, stroking my empty seat like it was me. No clothes off, no fucking—but the heat was insane. We eventually pulled back laughing it off as we returned to the booth. We dropped a lifestyle hint when Jake asked about our vibe. I said we love pushing boundaries together, open to all kinds of fun.

Back home, Tim and I were animals. The second the door closed, we were ripping clothes off, fucking on the living room floor. We fucked raw and hard, roleplaying Jake joining us. This morning, over coffee, we debriefed more. Tim’s obsessed with how bold I was, and I’m high on feeling like a sexy, desired hotwife with him watching. We think Jake’s open to the lifestyle, given his ease with our hints.

We’re planning another meetup with Jake—maybe back at the bar or our place .
David —we might grab that coffee to keep it flirty but professional

[athlete915]

Hey Ashley,

First, welcome to OHW! Second, thank you so much for sharing your experiences. Your posts are really well written and very enjoyable to read. Finally, congrats on the make-out session. That first step into physical play outside of a relationship is a big one. I'm glad it went well.

When I read your posts, I read them from Jake's perspective and wanted to offer you some thoughts. I've been involved with couples for over ten years, with most of my experiences being in the form of long-term, steady relationships with couples. Despite that experience, I still find it challenging to meet couples "in the wild." I can be out, meet a couple, and they can be showing a lot of signs of interest, but it is still hard to know for sure. For example, I can be playfully flirty with her to test the waters, and he can appear to be cool with it, maybe even encouraging it, but he may know nothing about the lifestyle and not be anywhere close to being ready for things to go further. Even if he understands he has cuckold desires, he may have never admitted them to his wife. Similarly, the wife may see it as just playful flirtation, or even if she does want to play with others, may never have admitted it to her husband. They may even be open with one another about their desires and at the fantasy stage, but still not ready to take the next step.

That's a long way of saying that it is tough to know who is interested in the lifestyle until you get to know them better. It wasn't until my fourth couple that I met a couple out in a vanilla setting (a club in Miami... okay, semi-vanilla) and brought them home that night. The others had been slower, or they were the ones who pursued me.

Of course, Jake should have no illusions by this point that you two are interested. I may not be the sharpest guy in the world, but when I can make out with a wife in front of her husband, it's usually a good sign that they want to play lol.

Before I let you go, I wanted to share a post I had written earlier. It's an incomplete list of things that couples should consider before playing. I'd suggest that you and Tim should give it a read, consider the topics individually, and then come together over a glass of wine (or three) and discuss them together. Where your ven diagrams overlap, you should have confidence moving forward. Disconnects can be areas for further discussion or potentially the starting point for establishing your limits and boundaries.

viewtopic.php?p=1568553#p1568553

Have fun, play safe, and I look forward to reading more about your adventures. Please let me know if you have any questions or would like to discuss anything I shared further.

Eric

[ash_hotgf]

I had coffee after work with David; David followed up with a short text on Sunday- Great talking with you. Let’s grab coffee soon;
David was going to be near my office and I spent the whole day half-working, half-daydreaming. I wore a fitted blouse with high-waisted pants, business but just enough flirt to keep me feeling sexy. Tim texted me little teasing messages throughout the afternoon. David chose a spot just a few blocks from my office. When I walked in, he was already at the counter ordering. He turned, smiled , and it struck me how different he looked outside the corporate setting. He handed me my latte. We grabbed a booth in the corner, away from the after-work crowd.

At first, it was all business chatter but the shift came quickly - laughed and gave him the safe answers first. He pressed a little more, like he was fishing for something underneath. The way he held eye contact, it wasn’t business anymore. There were these little sparks - his hand brushing mine when we both reached for the sugar, his knee almost touching mine under the table. Nothing explicit, but it was electric.

We sat there for over an hour. The conversation drifted into personal territory. When it was time to go, he stood close and his hand brushing the small of my back as we walked out. Outside, we lingered a second longer than necessary. He smiled and said we need to do it again. I just smiled back, teased him with we’ll see if you make the cut. He laughed, touched my arm lightly, and walked away.

I called Tim as soon as I left the cafe. He asked all the questions I knew he’d ask - Did he touch you, how close did he sit, what did you feel. By the time I walked through the door he was all anticipation. We poured wine and sat on the couch, and I told him everything in detail - how David’s hand lingered, how he looked in that casual shirt, the way his eyes didn’t leave mine. Tim admitted later that what really got him was imagining me sitting there with David, flirting openly, while he was at home waiting to hear about it.

If someone had told me a year ago that I’d be writing on a forum about grabbing coffee with a client and how my boyfriend was not only okay with it but thrilled, I would have laughed. But here we are, and I’m honestly having more fun than I ever expected.

[BallSpanking]

And your fun is only just getting started ...!

[sandy691196]

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[sandy691196]

I had coffee after work with David; David followed up with a short text on Sunday- Great talking with you. Let’s grab coffee soon;
David was going to be near my office and I spent the whole day half-working, half-daydreaming. I wore a fitted blouse with high-waisted pants, business but just enough flirt to keep me feeling sexy. Tim texted me little teasing messages throughout the afternoon. David chose a spot just a few blocks from my office. When I walked in, he was already at the counter ordering. He turned, smiled , and it struck me how different he looked outside the corporate setting. He handed me my latte. We grabbed a booth in the corner, away from the after-work crowd.

At first, it was all business chatter but the shift came quickly - laughed and gave him the safe answers first. He pressed a little more, like he was fishing for something underneath. The way he held eye contact, it wasn’t business anymore. There were these little sparks - his hand brushing mine when we both reached for the sugar, his knee almost touching mine under the table. Nothing explicit, but it was electric.

We sat there for over an hour. The conversation drifted into personal territory. When it was time to go, he stood close and his hand brushing the small of my back as we walked out. Outside, we lingered a second longer than necessary. He smiled and said we need to do it again. I just smiled back, teased him with we’ll see if you make the cut. He laughed, touched my arm lightly, and walked away.

I called Tim as soon as I left the cafe. He asked all the questions I knew he’d ask - Did he touch you, how close did he sit, what did you feel. By the time I walked through the door he was all anticipation. We poured wine and sat on the couch, and I told him everything in detail - how David’s hand lingered, how he looked in that casual shirt, the way his eyes didn’t leave mine. Tim admitted later that what really got him was imagining me sitting there with David, flirting openly, while he was at home waiting to hear about it.

If someone had told me a year ago that I’d be writing on a forum about grabbing coffee with a client and how my boyfriend was not only okay with it but thrilled, I would have laughed. But here we are, and I’m honestly having more fun than I ever expected.

This kinda organic stuff is always the best in the initial stages. No painful going through profiles, no losers, no flakes. Afterall you only go out / meet a guy organically only if his basics are good and you have chemistry.
+ in these workplace connections guys are always extra careful so its kinda safe and you get the time and space to make up your mind.
This being a pretend cheating kinda scenario.. you can pace it as it suits you & BF. You can end it whenever you want! No workplace guy's gonna make trouble over that!
Btw is David married / attached?

[ash_hotgf]

With David it’s been so natural, no pressure, just playful. And you’re right, the workplace setting adds this strange mix of safety and danger at the same time. I think that’s part of why Tim enjoys it so much too — it really does feel like pretend cheating. David’s single. Which honestly makes it even easier to enjoy, because there’s no extra drama or complications

[sandy691196]

Its somehow safer when the guy is married/attached. Its also a bigger ego kick since you are winning a "contested" battle so to speak ..
Maybe David is hiding his attached status just to seduce you the old fashioned way.
Next time make it clear that you don't mind him seeing other girls since you are kinda committed to your BF and hence you have no intention to become David's primary partner..

[ash_hotgf]

Tim and I had our second meetup with Jake last night, things definitely heated up. We invited Jake over to our place for a casual night, wanting a more intimate setting. I went for a flirty but casual - thigh leggings, low-cut tank top and my hair loose. Tim picked out a playlist with just the right vibe and we had drinks ready. The plan was to keep it fun see where the night took us. Jake arrived around 9PM, looking hot. We started with some card games, because it’s silly and breaks the ice. He’d tease me when I’d lose a round, saying things like You’re too distracting Ashley, I can’t focus. After a couple of rounds and another drink we switched to a truth or dare style game to spice things up. Jake dared me to dance for them, so I put on a slow, sexy song and swayed in the living room. Tim’s eyes were on me, Jake wasn’t shy about watching either. Then it was my turn, I dared Jake to show me his best dance move. He stood, pulled me up with him, and we ended up slow dancing. Tim watched from the couch, sipping his drink. Jake and I ended up on the couch and Tim slid over, his hand resting on my knee and Jake’s hand found my thigh too and I let it stay there. We were all laughing, but the tension was electric. Things escalated when Tim suggested we cool off with a movie, but nobody was really watching. I was between them on the couch, Jake’s arm around my shoulders, Tim’s hand on my waist. Jake’s fingers started tracing circles on my shoulder and I turned to him, and we started making out. His hand slid under my tank top, then higher. I glanced at Tim, who nodded; I could feel Tim’s hand tightening on my waist, urging me on. I reached for Jake’s jeans, feeling him hard , and started stroking him over his pants. My leggings were thin, and Jake’s other hand slid between my thighs. I was soaked, my hips moving against his fingers - no clothes came off fully, and we didn’t go beyond hands. I unzipped Jake’s jeans, slipped my hand inside, and started stroking him. Jake’s fingers slipped under my leggings he worked me with slow and firm strokes. It didn’t take long before Jake came in my hand. After what felt like forever but was probably 20 minutes, we slowed down. We wrapped up the night with some light chat, and Jake left around midnight and promised to hang again soon. We’re planning to invite Jake over again, maybe the weekend

[path22]

Wow, very good, things are moving quickly. I think the first blowjob is coming this weekend! Thanks for keeping us updated, Avantiii.

[Tryn]

That’s a HOT update, Ash! I have a few questions. How did it feel making Jake cum with Tim right next to you? Also, were you close to cumming or did you need something different to cum? Lastly, would you have cum looking at Jake or at Tim while Jake was rubbing your clit?

[zorro]

You are doing great, Ash! Your description of reaching into Jake's pants to stroke his hard cock till he came made me want YOU to hold and stroke my cock too. You are a very sexy woman.

Are you and Tim ready for you to fuck Jack? He is yours for the taking if you are.

[ash_hotgf]

Wow, very good, things are moving quickly. I think the first blowjob is coming this weekend! Thanks for keeping us updated, Avantiii.

Things are definitely heating up with Jake, but we’re still taking it slow to keep it fun and comfortable for both of us. A blowjob might be coming, but we’re not rushing it.

[ash_hotgf]

That’s a HOT update, Ash! I have a few questions. How did it feel making Jake cum with Tim right next to you? Also, were you close to cumming or did you need something different to cum? Lastly, would you have cum looking at Jake or at Tim while Jake was rubbing your clit?

What can I say , mix of power and connection knowing I was driving Jake crazy while Tim was so close - felt sexy and desired. As for me, I was so close to cumming when Jake was rubbing me , his fingers were hitting all the right spots. I think I didn’t quite get there because it was so new and I was hyperaware of both guys. Maybe a little more time would’ve pushed me over. If I had cum, I think I would’ve been looking at Tim.

[ash_hotgf]

You are doing great, Ash! Your description of reaching into Jake's pants to stroke his hard cock till he came made me want YOU to hold and stroke my cock too. You are a very sexy woman.

Are you and Tim ready for you to fuck Jack? He is yours for the taking if you are.

As for fucking Jake, we’re definitely feeling the chemistry is there. Maybe pushing things a bit further next time. Gotta keep that trust and connection with Tim rock-solid

[zorro]

Makes sense, Ash. Until you see Tim actually get off on how hot it is to see you enjoying another man's cock enter and move inside you, you would prudently go in baby steps. Once you can be reassured he is really good with it, then you can let go and follow your desires. I can hardly wait! lol I'm in with you vicariously on your excellent adventure!

[ash_hotgf]

Tim and I got a text from Jake yesterday, inviting us to a hot new club downtown this Saturday. It sounds like the perfect spot. We’re thinking this could be an awesome setting for our third meetup with Jake, where we might push the things a bit further. I’m planning to wear low-cut black dress with heels to turn heads. Tim’s already turned on, saying he can’t wait to see me own the dancefloor