Figuring it out

[Lookingforadventure]

Any chance of some pictures of those outfits? Headless would fine.

Let me think about that a little bit... but I appreciate the request.

[Mr1SexyGILF]

Any chance of some pictures of those outfits? Headless would fine.

Let me think about that a little bit... but I appreciate the request.

Thank You sincerely for taking the time to share your journey with us. It is most appreciated.

I think you will be quite pleasantly surprised at the confidence boost you would receive from a pic thread.

Mr GILF

[Michaels30309]

Doesn’t seem like she needs the confidence boost… great writer, great self-awareness, great contemplation of both her actions and consequences…

Love the attempt at providing the “it’s not for me, it’ll be great for you” incentive…

[Lookingforadventure]

Doesn’t seem like she needs the confidence boost… great writer, great self-awareness, great contemplation of both her actions and consequences…

Love the attempt at providing the “it’s not for me, it’ll be great for you” incentive…

LOL. I was thinking about replying "I'm not sure I need a confidence boost" but then I thought I sounded arrogant. Now you've said it for me and I'm blushing. Thanks for the compliments.

And I will seriously think about posting some photos. I've just had some bad experiences before with images getting shared elsewhere without my permission, so I'm a bit cautious.

[Michaels30309]

Then skip posting and keep your comfort level high and risk low… works for many. I’m sure the gawk would be fun for many but not worth the trade of your concern… I think D is the one supposed to have the angst in your adventures.

[R_H_NC]

Doesn’t seem like she needs the confidence boost… great writer, great self-awareness, great contemplation of both her actions and consequences…

Love the attempt at providing the “it’s not for me, it’ll be great for you” incentive…

Yeah, sorry MrGILF, that one was a bit obvious.

Not that I don't second the request.

[Michaels30309]

You should make us a 5 course delicious meal + great wine to make yourself feel good about your ability to host and be a great chef. You’ll also really enjoy practicing doing dishes…

[Lookingforadventure]

You should make us a 5 course delicious meal + great wine to make yourself feel good about your ability to host and be a great chef. You’ll also really enjoy practicing doing dishes…

Hee hee. I actually do enjoy cooking and hosting, but then you will have to do the dishes.

And go easy on Mr. GILF. I have a soft spot for him.

[Michaels30309]

You should make us a 5 course delicious meal + great wine to make yourself feel good about your ability to host and be a great chef. You’ll also really enjoy practicing doing dishes…

Hee hee. I actually do enjoy cooking and hosting, but then you will have to do the dishes.

And go easy on Mr. GILF. I have a soft spot for him.

Understood and agreed… so about the pictures?

[Lookingforadventure]

Let's change the subject from the idea of photos, shall we?

Here's the write-up about my solo hotel date with G.

----

I pulled up to the hotel and texted D to let him know I had arrived. I was a bit early, but G was even earlier. When I looked up from my phone, I saw him approaching my car. I got out, smiled at him, and gave him a kiss.

His lips and body felt good against mine. I could have kissed him in the parking lot for a long time, but I was mindful that someone I know might drive by.

Pulling back slightly, but still keeping his arms around me, G told me that there was bad news. We had asked for early check in, but our room wasn’t ready yet. I gave him another quick kiss and said that that was ok. I’m pretty happy to go with the flow. G took my hand and we walked to the gazebo on the hotel grounds to wait it out.

“I’m a little bit nervous,” I confessed as I sat next to him on the gazebo bench.

G wanted to know why, but I couldn’t put my finger on it. Maybe it was just because this was my first time having sex without D there. It felt like a big step, even though I had had sex with G before. G put his arm around me on the bench and pulled me in for another kiss. My nerves soon disappeared.

He had a small cooler bag with him. When we broke our kiss, I asked him what was in it.

“Some champagne plus a couple surprises,” he told me with a smile. He took one of my legs in his hands and put it across his own so that he could stroke it. I was grateful that D had helped me fully lotion my body before I left. I was soft and smooth all over

G apologized. He had intended to bring flowers, but the store he stopped at on the way didn’t have anything nice.

I was going to make a joke by quoting Pretty Woman (“I appreciate this whole seduction thing you've got going on here, but let me give you a tip: I'm a sure thing”) but I wasn’t sure if it would land the right way. I mean, I’m not ACTUALLY a “sure thing”, although on this occasion I was pretty sure that G was going to get into my panties pretty quickly.

Instead, I thanked him for his good intentions and gave him another kiss. It turns out that the gazebo is the smoking spot for hotel guests. As we were kissing, someone came outside for a cigarette. G and I decided that was our sign to leave.

G went to check on our room and I went to grab my bag from my car. (Based on the advice of the women in the ladies lounge, I had packed a “sex date bag” with condoms, lube, a change of lingerie and a few other essentials).

I met G as he was walking back out of the lobby. “No luck,” he told me. “The room is going to be another 30 minutes.” We decided to go for a drive.

G had lived in my city as a child, so he said he’d take me to see his childhood home. We chatted as we drove, and his hand frequently found its way to my leg -- stroking the skin above my knee and sliding up towards my thigh.

We found his elementary school, drove down several streets in his neighborhood, and parked across the street from his old home. He pointed out where he used to cut through people’s yards to get to his friends’ homes. It was cute to think about him in his younger years.

Plus, there is something about parking in a car with a sexy man that is a real turn on. I told him that before he put the car back in drive, he needed to kiss me again. He was happy to oblige. He also slid his hand further up my leg. I spread my legs for him a bit, and he got a good feel of just how wet he was making me.

His fingers parted my pussy lips and I felt my body quiver in pleasure. We decided to drive quickly back to the hotel.

In the lobby, the hotel clerk smiled and handed G the key to our room. There may have been a knowing look on her face, but I didn’t care. We pushed the elevator button, and waited for it to arrive. We had already been waiting for 40 minutes to get into the room, one can only have so much patience. We decided to take the stairs.

G suggested that I go up ahead of him. He was not subtle about ogling my ass as we went. I gave it a bit of extra sway as I walked. If he wants to look, I might as well give him a show, I figured.

The top of the stairs was directly across the hall from our room. G got out his key and a maid gave us yet another knowing look. It made me blush. I felt like a high school kid on prom night - everyone knew what we were about to do, but I was so excited about it that I didn’t care.

We got inside the room and G stripped off his shorts, saying that his erection had been getting very uncomfortable. He took off his shirt as well and went to put the champagne in the mini fridge. I laughed at his boxers and socks look. He responded by pulling me into his body for a deep kiss.

He walked me backwards towards the bed and pushed me down. He told me he couldn’t wait any longer. He slid my dress up, spread my legs, and used his tongue to push my lingerie to the side so he could taste my wetness and massage my clit. It was amazing. I think I came after only a couple of minutes.

I think that’s when I decided to give him a better demonstration of the lingerie that D had picked out for the occasion. I stood up and removed my dress, as G got out of his boxers. As I dropped my dress to the floor, G was very appreciative of the lace teddy. I did a little spin, and I’m pretty sure the thong did as it was intended. With that said, the teddy only stayed on my body for a couple of minutes. Then G was between my legs again.

Eventually, we decided to break out the condoms. G lifted my legs up on his shoulders and penetrated me deeply. I had already orgasmed a few times, but this was intense. I could feel the tip of his cock hitting my g-spot and my juices leaking out around him. I told him that I was going to cum, and he smiled.

“Cum for me baby,” he said, and it sent me over the edge.

He fucked me slowly after that, enjoying the feeling of being inside me. I stroked his chest, and sometimes he leaned forward to kiss me. He began to pick up speed. I could see his orgasm building. He pulled out and climbed on the bed next to me. He removed the condom and asked if I wanted to take a very special photo for D.

I laughed because, as we planned for our date in the preceding weeks, we had talked about fucking on the hotel desk. I was going to be a sexy librarian and he was going to cum all over my face and glasses so that we could send a sexy photo back to D. Alas, we had forgotten that part (the desk looked pretty flimsy anyway) and I wasn’t wearing my glasses, but the idea of a cum facial was still super sexy.

I told him I wanted his cum all over me. He was happy to fulfil my desire. He grabbed my phone for me and I held it as he stroked his cock inches from my face. The first shot landed near my mouth. Another on my cheek. Then one on my nose. I took a photo of my smiling, cum-covered face inches from G’s still-hard cock...and a second photo as I licked him clean.

I sent them to D. He responded immediately and told me how much he loves my slutty side

I went to the bathroom to clean up a bit as G popped the champagne and brought me a glass. We toasted to our first solo date and to how well it was going. He also brought out some berries, and fed me one.

“Pretty Woman was right, it brings out the flavor of the champagne,” he said to me as I took the berry from his fingers. I smiled to myself because I hadn’t told him that I had almost quoted Pretty Woman to him earlier in the gazebo. It seemed like a funny coincidence, but one that made me happy by how in sync we were with each other.

I lay back naked on the bed to sip my champagne. G got on the bed beside me. I had a mischievous thought, so I dipped a strawberry between my pussy lips and lifted it to his lips. It was creamy and he smiled as he took it on his tongue.

He dipped a finger in his champagne and traced some of it across my nipples. Then licked it up with his tongue. The champagne flutes were soon put down in favor of round two.

We ended up spending about three hours fucking, kissing, cuddling, and fucking some more. Sometimes it was passionate and lust-filled. Sometimes it was tender and sweet. I enjoyed licking, kissing and sucking his cock to revive it after a break. I enjoyed straddling him and grinding my wet pussy against his hard cock as I kissed him. I enjoyed being bent over the bed as he took me from behind and slapped my ass a bit. I enjoyed watching his face as he orgasmed deep inside me. And I very much enjoyed the multiple orgasms that I had over the course of the afternoon.

Five condoms, and a few cell phone photos later, we were rather exhausted. I lay with my head on G’s shoulder and my hand stroking his chest. I told him that I had had a really great time. I hoped we could do it again.

He said he would love to...anytime D and I wanted. Plus, we had neglected to use the desk, the jacuzzi tub, or the shower. We had a lot of things to still check off our list.

When I got home, G had sent a text telling D how amazing the afternoon had been. D responded to him after I walked through the door. He told G that I was absolutely glowing. He thanked G for taking such good care of me. I thanked them both for the wonderful experience.

[Michaels30309]

Thx for sharing your adventure… and great writing. Nice to see humanness and understanding to the impact of this adventure. Great perspective for many with a touch of literotica-style flair too. Kudos.

[Seekingmore12]

At the risk of outing myself…

I do have to say K, you captured this and other adventures very skillfully, this last post and the adventures are special to me.

Thank you D and K for involving me in your quest to figure it out ! You are truly special people.

[Lookingforadventure]

Thx for sharing your adventure… and great writing. Nice to see humanness and understanding to the impact of this adventure. Great perspective for many with a touch of literotica-style flair too. Kudos.

Thank you! See? You didn't even miss not having photos

[Lookingforadventure]

At the risk of outing myself…

I do have to say K, you captured this and other adventures very skillfully, this last post and the adventures are special to me.

Thank you D and K for involving me in your quest to figure it out ! You are truly special people.

It has been, quite literally, my pleasure! (A little pleasure for you and D too, but mostly me).

[Wannabee]

Hi Lookingforadventure. Thanks for your posts. I just discovered them and read them all from start to finish. Like a great book, I couldn't put it down. Not only are you a hot and sexy lady, you're a fantastic writer. I can't wait for the book. Please continue to share your wonderful adventures with us.......... and btw, what happened to those photos?

[CurvyNerdMILF]

It’s fun to see that you have also been able to make use of OHW’s gentlemen.

The date sounds wonderful. I’m glad you also have enjoyed the thrill of a hotel date and have some more fun in store.

[Lookingforadventure]

Hi Lookingforadventure. Thanks for your posts. I just discovered them and read them all from start to finish. Like a great book, I couldn't put it down. Not only are you a hot and sexy lady, you're a fantastic writer. I can't wait for the book. Please continue to share your wonderful adventures with us.......... and btw, what happened to those photos?

Hello Wannabee. Thank you. You literally made me laugh out loud with that last question.

It has been great to find this forum and read other people's stories and advice. I thought I could return the favor. Plus, it has been fun for me to think back on the past year and remember the details.

[Lookingforadventure]

It’s fun to see that you have also been able to make use of OHW’s gentlemen.

The date sounds wonderful. I’m glad you also have enjoyed the thrill of a hotel date and have some more fun in store.

Thank you. Technically, I met G through a different site (AFF) and he steered D and I here after we came back from our break and were figuring out how we wanted to proceed. I'm glad he did. Hearing other people's stories and seeking advice from other ladies has been super helpful.

With that said, yes, he's been a gentleman and I've certainly "made use" of him

[Michaels30309]

“Made use”… as if?!?

For centuries women are always treating men like a piece of meat simply for their personal pleasure?

Oh wait… maybe I’m getting that wrong.

[Lookingforadventure]

“Made use”… as if?!?

For centuries women are always treating men like a piece of meat simply for their personal pleasure?

Oh wait… maybe I’m getting that wrong.

Don't even get me started on the historic objectification and sexification of women!

As for G, I will take back my cheeky word choice. While I have received great personal pleasure from my encounters with him, I would never actually classify them as "making use" of him. I think that's why I like a slow and cautious approach to choosing play partners. When you've developed a true friendship and connection, then your time together is more than just using someone for sex. It is intimate and playful, erotic and beautiful, quirky and meaningful...all wrapped into one.

[Seekingmore12]

“Made use”… as if?!?

For centuries women are always treating men like a piece of meat simply for their personal pleasure?

Oh wait… maybe I’m getting that wrong.

Don't even get me started on the historic objectification and sexification of women!

As for G, I will take back my cheeky word choice. While I have received great personal pleasure from my encounters with him, I would never actually classify them as "making use" of him. I think that's why I like a slow and cautious approach to choosing play partners. When you've developed a true friendship and connection, then your time together is more than just using someone for sex. It is intimate and playful, erotic and beautiful, quirky and meaningful...all wrapped into one.

Well said :-)

[CurvyNerdMILF]

I feel chastened. I didn’t mean to demean the intimate and friendly connection shared by any lovers. (Including me with my own…) I also cultivate and feel a great deal of affection and connection with my lovers. I did not mean to imply that a person of any gender would be “made use of” as an object. I was more reflecting on how fun it is that there are connections right here among OHW community members.

I will now hang my head in shame and slink off to my corner.

[R_H_NC]

I for one caught the intended humor in the use of the term.

It was quite obvious from the telling of the encounter that there was plenty of give and take (and mutual satisfaction) by both.

[Michaels30309]

And I hope y’all fully understand my intended sarcasm / humor too?

[Lookingforadventure]

Not to worry everyone, I think we all knew what each other meant.