My First Solo Encounter

I finally had my first solo encounter. I'll have to write the long history of my other encounters and how we got here after this post; I had to write about this first. (The memories are still fresh!)

We have been in Maui for vacation. I decided to post a Craigslist ad. This is what it said:

Hi all!
I am here in X for the week (until Jan 12), and looking to make some hot connections while I am here... Even one would be amazing!! A little about me:
I recently graduated with my masters degree, exercise daily, love baking, volunteer, and am currently a stripper (it's true!) :D I am sweet, smart, sexy, and thoughtful, and I am looking for similar qualities in a man I can share a brief, but spicy, encounter with!! My stats: 5'5", 125 pounds, dark blond hair, blue eyes, great ass, size B tits :D (My ad was flagged and removed, so while I don't have pics here, I will be sure to respond with some) My ideal match is educated and takes care of himself physically and mentally. You are sex positive and know what you like in bed. You don't mind that this will (most likely) be a one-time hot encounter. Please reply with G-rated pictures of yourself (I honestly don't care what your cock looks like), and a little bit about you. Looking forward to meeting you! xoxo
K 

I got more responses than I knew what to do with, and about seven of them seemed like good fits: I thought their photos were attractive, and they wrote intelligent, funny, or thoughtful emails. Ironically, I decided to respond to the shortest email. My past behavior was to always respond to the longer ones. But I was most attracted to this guy's photos.

Here is our email chain (with email addresses and phone numbers removed- you'll notice there is not a whole lot left to them, haha):

On Fri, Jan 4, 2013 at 5:01 PM, G G wrote:

Aloha,
Hi I'm a local surfer. I am a college graduate, and I work in real estate escrow, but I love to have fun and I love exciting sexual encounters. ;) I'm 5'10,170, very athletic body, brown hair and brown eyes. You sound gorgeous, I'd love to hang out and see if we click. Can I see a pic?

On Jan 4, 2013 10:11 PM, "K B"  wrote:

Aloha!!

Thanks for your nice email :) I think you are pretty hunky ;-)

First of all, here are pictures of me (one album has more vanilla pics, the other has sexy pics):

Are you open to a primarily sexual encounter? Would you be willing to meet me somewhere near where I'm staying and then head back to my condo? I am available pretty much whenever, although I have a preference for late afternoon/early evening :)

Let me know what you think!!

Also- I want to assure you that I always practice safer sex, using condoms for all vaginal sex. I was also recently tested for HIV, chlamydia, gonorrhea, and syphilis and all came back negative :-) (I know, not the sexiest topic but a necessary one!)

xo

K

On Jan 4, 2013 10:50 PM, "G G" wrote:

Hey. I love your pics. I am only looking for a one time encounter, and early evening is ideal for me as well.
I too was recently tested for everything and clean.
Are you on maui now?
Can I text you to coordinate?
G

To: "G G"

Yes I am in Napili :) my number is XXX-XXXX. Talk to you soon!

K

Not a whole lot of information flying back and forth, right? That's not my typical style. But I just went with it. 

Then the texting ensued (the times are all off by two hours):

G G : Hey katie? 11:36 AM

G G : This is G 11:37 AM

Me: Hey! How's it going? :-) 11:50 AM

G G : Hey I'm good, just wandering if you might be able to meet today around 1-2pm?

I know its early, but that's the only chance ill have for a couple days... 11:53 AM

Me: Hmmm I don't know that I'll be able to do that today. Can we stay in touch and can

you let me know when you are available again? :-) 12:25 PM

G G : When will u be free? 12:29 PM

Me: I'm not totally sure. Possibly later in the day today or the next few days in the late

afternoon or early evening 12:42 PM

G G : Ok well ill call you later to see if today can work, I'm headed toward X now to go

surfing and I should be done around 3 or 4, maybe we can meet then befor12:54 PM

G G : e I head back to Y 12:54 PM

Me: Alright sounds good! :-) have fin surfing! 1:01 PM

Me: *fun 1:01 PM

G G : Hey whats up to? Wanna meet me? 4:39 PM

G G : I'm done surfing, about to head back to Y but I can hang out for a little if you want

5:00 PM

Me: Sorry I missed you!! I guess today isn't going to work out for me after all. I hope you

have a good rest of your day though! 5:16 PM

G G : Haven't left X yet, you busy? 5:17 PM

And a couple days later:

G G : Hey katie, can you meet tonight around 6? 11:41 AM

G G : ? 2:18 PM

Me: That might work for me :-) are you available a little later, like around 7? 3:37 PM

G G : No, 6-6:15 is about the latest I can meet... 3:47 PM

Me: How long are you available for? 4:08 PM

G G : Till 730-8ish 4:22 PM

G G : How long do you want spend together? 4:27 PM

Me: That sounds good :-) what do you think about just coming to my place at about 6:30?

4:32 PM

G G : That sounds perfect 4:34 PM

G G : What's your address? Do I need to bring anything? 4:47 PM

Me: I'm at the X :-) feel free to call me when you get here if you hace trouble finding my

building! I have condoms (just Trojan regular) and lube :-) bring your smile and yourself!

I'm excited for some good fucking ;-) 5:29 PM

G G : Ok 6:19 PM

Me: Does this still sound fun to you? I only want to do this if it sounds fun to you too!

7:09 PM

G G : Hell yeah! 7:11 PM

G G : Do you know how hard it is to find a young hot girl that wants a completely nsa

hookup! I'm stoked! 7:14 PM

Me: Haha okay!! Awesome :-) :-) I just realized I don't know how old you are 7:16 PM

G G : I'm 28, and you? 7:16 PM

Me: I'm 24 :-) 7:17 PM

G G : Perfect! 7:17 PM

Me: Let's meet in the lobby of the resort :-) 7:21 PM

G G : Ok 7:21 PM

G G : I'm going to in kapalua for a little now, see you in an hour ;) 7:22 PM

Me: Sounds great!! :-) 7:23 PM

 

What was going through my head with all of this?

I was FREAKING OUT. Excited, but super nervous. Horny as hell; really turned on. J and I were both so turned on earlier in the day about it all that he used my pussy for a long time, although he didn't come so that he could shoot an extra big load into my pussy afterwards. J really wanted to use my pussy after I had another cock in it.

J and I had been out all day walking and snorkeling, and I needed a shower. J decided he would go for a run while I got ready and then hang out in our resort so that he could periodically stop by the door and listen. HOT. It also helped me mentally, because I was honestly feeling a little nervous about meeting someone totally by myself. Working and volunteering in the sexual violence prevention field has me a little (unnecessarily) freaked out about perpetrators.

So J went out for his run and I took my shower. I put on a little make up and blow dried my hair, and put on my favorite perfume. I put on some cute shorts and a top and looked at myself in the mirror. I felt hot and pretty and really ready to give this a try.

I had a lot of racing thoughts: What if he shows up and I don't find him attractive? What if we start talking and he acts like a bro? What if we start making out and I am turned off by the way he kisses? What if we start having sex and it just isn't working like I want it to? What if all I have to report to J afterward is that it was a lukewarm encounter, or worse, an awful one because the guy was a jerk or inconsiderate or a crummy lover?

I breathed myself through it, allowed myself to feel nervous and the adrenaline coursing through my legs and arms. When J got home he hugged me and reassured me that I was capable of calling it off if the vibe was weird or I didn't like the guy. He gathered his bathing suit and some food and his book and headed off to the pool. 

I went toward the lobby area to meet my new friend.

We took about ten minutes trying to find each other; he had accidentally parked in the wrong parking lot. Finally, we found each other, and he gave me a hug as a greeting. His body felt firm and his hug felt sincere. I breathed a sigh of relief. I liked his friendly voice, and I immediately started launching into personal history questions: Remind me what you do? How long have you lived here? Do you like it? How often have you met someone off of Craigslist? Were they good experiences? We talk about all of that, and about my experience stripping, and the kinds of sexual experiences I have had. He tells me prefers to be dominant during sex. I become really excited; I love being submissive. I tell him that sounds great. I tell him I sometimes like pain, depending on the vibe with the person I am with: spanking, hair pulling, etc. I see J at one point outside the front door, listening in. I am a little disappointed that all he would be able to hear is some light conversation and not the pounding fucking he wants to hear.

G then offers to give me a massage to help break the ice. I readily agree; I am what J and I call a "massage whore." Ha. Stripping has meant that for the past few months my back and shoulders are consistently tight and ache-y. I love that he suggests a massage.

He sits on my back (our clothes are on still) and begins rubbing my back and shoulders, palpating my muscles. I totally bliss out. We stop talking for a minute. After a few minutes he leans down and starts kissing my face and neck. I turn my head so I can kiss him back. He's not my favorite kind of kisser (he uses a quicker, more darting tongue- not my favorite), but I roll with it. 

I decide to finally get up and close the blinds. J and I have been staying in a small studio condo on the second floor and the slider door faces inwards toward a large grassy area and courtyard. I leave the screen door open; the front door screen has been left open, too, for J's listening pleasure.

G asks if I can turn on some music, and I start searching for a good playlist online. We both start  taking our clothes off, and he starts rubbing my naked body down, caressing and kissing. When I turn around I push him toward the bed so I can go down on him. His cock is hard and he likes how I can take his whole cock into my mouth and go up and down really fast. I look up at him and his face is filled with pleasure.

When I look up at him again, he stands up swings me onto the bed. The force took me by surprise and excited me. He started going down on me and got my outer lips really wet with his mouth. He starts playing with his cock near my pussy and I ask him if he wants a condom. He says yes.

He penetrates me and starts pounding away. It feel awesome. After a few minutes, he picks up my body and forces me in a different direction on the bed and continues to pound away. His dominant energy had me going. He just used my body how he wanted to; I love that. I get off so much on another person just using my body to make theirs feel good. 

He alternates between shoving my legs up to my face so that he can pound it and going down on me. He tells me over and over that I have a really nice pussy. He holds my jaw really firmly and hits my face a couple of times. He kisses me roughly and spreads my legs open and closes them shut and shoves them up to my face and back down.

He roughly rolls me over to my stomach and uses my pussy from behind for a little bit. He spanks me a couple times. But after just a few minutes he decided to roll me back over to my back.

I am so completely turned on that I know I am going to squirt. He starts pounding away and when he pulls his cock out to go down on me, I come. A LOT. His face is pure joy. "A squirter!" he exclaims. He starts rubbing my clit furiously, and alternating between pounding my pussy and pulling out so I can come. I soaked the sheets.

He then tells me that when he is going to come, he is going to pull out and take off his condom, and come on my stomach. Is that okay with you? he asks. I nod vigorously. I LOVE come on me. LOVE IT. 

He continues to pound my pussy. I decide I want him to come and I tell him a few times. Come on my stomach. I want your come on my stomach!! He finally pulls out his throbbing cock, whips off the condom, and comes all over my stomach. It was so hot.

We laid on the bed for a minute or two, panting. I forgot that there was a fan in our unit, and he decides to turn it on. He cleans up, we chat for a minute about how hot the whole thing was, and then he leaves (but not before he mentions that he would totally do it again before we leave Maui).

I find J, and when we are finally able to talk about it all, I use the encounter as fodder for dirty talk. I tell him about it all. All I do is take his cock into my pussy and lay on top of him while I tell him all of the details. As I near the end of my story, J comes. I can feel a huge load filling my pussy up and it feels so amazing.

Getting ready for bed, I can hardly walk. J and I had an hour long pounding session earlier in the day, and then my session with G, and then my second session with J left my pussy super swollen and sore. I rest on the couch with some ice pressed against my lips.

Before bed, J again wants some dirty talk and a release. I offer to give him a hand job while I talk to him about hot wife encounters. He comes in my hand. I love the feeling of his hot come all over my skin. I go to bed turned on and wake up the next morning turned on. Amazing.