Rubies and Diamonds

My flight was delayed from Milwaukee to Boston and so I did what all business traveler do on a delay, head for the bar! I sat down and ordered a tall Stella Artois and the first taste was so refreshing, I almost killed it in one gulp. The woman sitting next to me said, “Thirsty, huh?” And I said, “Long day of travel and work, I feel like I earned it.” She laughed and said, “I hear ya. Long day.” And I replied, “Cheers” and we both took another sip.

Melissa was from Andover and was returning from a Pharma Trade Show in Minneapolis. She was a good conversationalist and we shared stories of our latest travels. Mine was from Seattle where I attended a conference for investment banking and my flight began with a 2 hour fog delay, then a tarmac delay, and when I arrived in Milwaukee on this hot July day, I found out Thunderstorms were preventing my return.

She had a small delay in Minneapolis but was running late from the trade show due to the Union help at the convention center giving her grief over crate moving and electrical costs. Like she didn’t have more important things to worry about. She ran to the gate and just about missed it if it weren’t for the pleasant gate attendant.

She was in her early 30’s, unmarried, and no kids. She was cute in her 5’6 frame and filled out her navy blue pencil skirt and light blue silk blouse nicely. Her tits stretched the silk blouse out nicely. Her black pumps added about 3 inches to her height. Her hair was blond and fell to just below her shoulders, professional cut and style.

We chatted about our work and how much we traveled and which place were the nicest and which places we loathed when the text alert came across saying we were delayed yet another hour.

“I’ll have another please”, I said to the bartender and Melissa said the same. I asked if I could move closer to her as other travelers were deplaning and being met with the same weather delays which began to fill the bar area. She said, “Sure”. And I moved my backpack and carry on to the next seat over.

I was mid thirties, no kids, and recently divorced, mostly due to the extensive travel. I lost the dog and the house in the “custody” battle but didn’t really care. I was wearing a gray athletic cut suit and white shirt with black Johnston & Murphy shoes. My hair is black and nicely styled. I stand about 6ft.

Melissa excused herself and ran to the ladies room and I asked if she wanted another drink and she said yes. She took her carry on which I thought was weird but left her backpack, also weird. But whatever. She returned and said that she needed to get a bit more comfortable and was rocking a pair of navy Nike Elite leggings, an orange sports bra and a white dress shirt with navy blue with orange stripe Saucony running shoes. She pulled her hair back into a pony tail and joined me at the bar. “I had to get comfortable”, she said. “I didn’t think you could get any cuter before you left but I guess I was wrong.” She blushed a little and said, “Thank you, very nice of you to say.”

With this, we directed our attention to what work outs we do. She was an avid yoga, running and Pilates kind of girl and I was a classic runner and plyometric exercise kind of guy. And we complimented each other on our toned bodies and commitment to health and self preservation. Then we ordered another beer.

Ping, flight cancelled. She looked at me and said, “I had a feeling that was going to happen.” And I replied, “Summer travel always has its challenges, we better search hotels before more flights get cancelled.” I opened the Hilton App and searched and found the Downtown Hilton on Wisconsin Ave. and booked a king size bed and before closing the app, asked Melissa, “Need me to reserve a room for you? App is open.” She said, “No thank, I just booked the Hilton Downtown”. I said, “great, want to share an Uber? I just booked the same location. They have a great bar.” She said, “Sure, lets finish these and head out.”

We got to the hotel and we both checked in. I asked her if she wanted to grab a bite to eat after we settled in and she agreed to meet in the lobby in 20 minutes.

I ran to the room, quickly showered away the humidity and slight sweat stench that accumulated from the days travels and got into a pair of Lucky Jeans, white seersucker shirt and Covina flip flops and headed to the elevator. The door opened and Melissa was inside wearing tight blue jeans, pink shirt with white body suit underneath along with Havaianas flip flops. I said, “Damn, you get cuter by the outfit!” And she responded, “You aren’t looking to bad yourself.” And I now felt the redness fill my face.

“Any place you have in mind?”, she asked. I said, “There is a great little Cajun food restaurant nearby. Do you like Cajun?” She said she was up for anything. We stopped at a small bodega and picked up a bottle of cheap red wine and a 6 pack of Red Stripe.

We dined on fantastic Cajun food: Alligator, shrimp etouffe, and cray fish. She laughed when I placed their carcasses on my finger tips and gave an impromptu Prince concert. And we killed the rest of the beers and wine. We were both a bit tipsy.

We walked back to the hotel and the humidity of the night was wearing off a bit and felt refreshing. She locked her arm around mine and said she drank too much but our flirtation had grown from the airport bar and dinner solidified a mutual attraction to each other.

I got in the elevator and pressed my button and she said, “Awe, I thought we could hang in my room for a drink.” And I said, “What floor?”

We got into her room, a nice king size of her own and she hit the mini bar. I settled on a Grey Goose and soda, Melissa opted for a Tangueray and Tonic. I sat on the couch and she sat in the chair opposite me. We flirted a bit more and it lead to a game: Marry, Date or Fuck. And I lead with, “Marry, date or fuck: bartender at airport, concierge at hotel or waiter at Cajun place?” She laughed and said, “ Marry the bartender: responsible chap. Date the concierge: nice but meh. Fuck the Cajun waiter: super hot Latino.” I laughed and pictured her choices playing out in real life: practical yet adventurous.

Her turn and she asked: “Hotel receptionist, Cajun hostess, or me?” I laughed at her choices because in my mind I was thinking I wanted to fuck all three and then straightened my face and said: “Marry you” and she interrupted, “I thought for sure you would fuck me.” And with that I leaned in closer, and said, “Couldn’t I do both?” and then leaned in for a kiss.

She accepted and our tongues danced around each other’s mouths. We made out for a bit when she asked to be excused. I really did not want her to leave the room for fear of her changing her mind about what was happening and where I hoped it would go.

I was sipping my vodka and soda when she emerged from the bathroom wearing a red corset which pushed her tits up and exposed just the right amount of cleavage, red satin panties, red satin garter belt, and black stockings, her heels were back on and as she did a small twirl, the red bottom of her shoes seemed to complete the outfit. Her hair was down and swayed with the twirl. I dropped my drink.

“Amazing! You just keep on surprising me with these great outfits!”, I said as I stood up and walked toward her. I embraced her in a hug and lean in enough to catch her perfume. She said, “I bought this in at the Mall of America and didn’t know when I would be able to wear it. I love to dress sexy, it makes me feel so feminine.” I replied, “Happy we met, you are stunning. Words really can’t express you beautiful you are.” And we kissed.

I reached around and felt her firm ass and slowly worked my way around her, kissing her neck and nibbling her ears, and fondling any part of her I could. She moaned in pleasure. She stopped me and pushed me back just enough to unbutton my shirt and let it fall to the floor. She wrestled with my belt and undid my jeans, pulling them over my hips, and down to the floor, I stepped out of them. She began rubbing my cock through my Calvin Klein Black trunks and it started receiving the message as blood filled it and it began getting hard. Now I was moaning in pleasure.

We kissed again and then she began working her way south. Sucking on my nipples, licking downward until she got to my happy trail and started to pull down my Calvin’s. She knelt in front of me and took me into her mouth. She pulled my cock parallel to the floor and worked her hand back and forth while tongue lashing and sucking the tip. I went hard quickly and enjoyed the moment. Her eyes rolling to the back of her head as she looked up at me, slurping and sucking my knob. She was working me with one hand and her mouth while her other hand went to her pussy and began rubbing it through the silky soft satin.

She stood up and pulled my cock northward, continuing to stroke it she gave me a kiss. We let out tongues dance around and then I headed south. Pushing her breasts up in the corset and slowly pulling her panties down. I knelt down and began kissing her around the outside of her pussy lips and then her inner thighs. She was pushing my head toward her vulva but I resisted and kept trying to build momentum in her growing orgasm. I succumbed a few minutes later and spread her apart and lapped her wetness up with my tongue, settling in on her clit I flicked it with my tongue and she pushed my face into it, loving the touch of sex I had finally given her. I continued to lick her sweet pussy and she built into an orgasm and released her flow all over my face. I couldn’t get enough, I continued and brought her to another orgasm.

I stood up and we kissed. I moved her slowly to the bed and removed her corset before laying her down. Her tits were amazing with hard nipples sticking out above flat abs and an amazing summer tan.

I laid on top of her and she welcomed me by wrapping her legs around me. My cock bumped her pussy a few times and she moaned each time as if begging for it to enter her. A quick adjustment on my end and my cock was against its opening and working its way in without any help. She engorged my cock with her silky wetness and I slowly entered her. She moaned with pleasure as I drove deep inside her. As I was fully inside her, I felt my balls touch up against something in her perineum. I freaked a bit an pulled out of her.

I asked Melissa, “My balls just hit something when I was inside you, sorry but I am curious what it may be?”, I said. And she rolled over and exposed a Ruby Anal Jewel and I was so pleased. “Wow, again with he outfits...”, I said. She replied, “I love sex, all forms and ways. I hope you don’t mind?” I said, “No, I love it. I love adventurous sex as well! I wish I brought mine!”

She rolled off the bed and pulled out a small travel bag and opened it up. In it was a We Vive, a Dildo, a vibrator, Ben Wa balls, and another anal plug. And she said, “Well, you can borrow mine if you want, it’s clean.” And with that, I jumped on all fours and said, “Can you help put it in?” Melissa ran to the bathroom and got her lube and inserted the Diamond Anal Jewel in my ass.
We began kissing again and we played with each other while doing it. She was working my cock into another hard on and I was massaging her pussy to rejuvenate the wetness she had a few moments ago. It didn’t take long for both of us to be excited again and she pilled me on top of her. My cock slid in easily this time as we apparently had mastered each other’s orifice’s. The anal jewel in my ass was pressing against my prostrate and the feeling went direct to my cock. Melissa said she loved the anal jewel as it rubbed against my cock when I thrust into her. We fucked missionary for a few minutes and then changed to doggie. The sight of the Ruby in her ass as I fucked her from behind was awesome. I would play with it, pulling it in and out at various positions of my insertion and Melissa moaned in ecstasy when my cock would collide with it from the inside of her pussy. She built into and released another orgasm while in this position and her pussy gleamed in her cum.

I pulled out and laid down, she straddled me and put her back to me. As she slid up and down on my shaft, her Ruby sparkled in the light. She reached under and played with my Diamond and it caused me to explode gobs of cum into her pussy. She felt me release and fill her up and she left the Diamond alone and dropped backward onto me. I fondled her tits and caressed her body as I slid out of her cum soaked pussy. The cum leaking out of her, onto and around my cock and anus and finding it final resting spot on the bed, adding to an already large wet spot.

We hung out, cleaned up as best we could, especially the toys, and finished our drinks. I got dressed as did Melissa, this time in a pair of navy blue with white polka dot silk pajamas. Again with the outfits! We snuggled on top of the bedspread and talked about how much fun sex is but how hard it is to find open partners, or to be open with partners who may not be as adventurous. And we complimented each other on our openness, or adventurism, and our performance. We had made a strong connection this evening.

After about an hour, I asked, “ Do you want to move to my room since we pretty much destroyed your bed with our sexual juices? I feel like the chivalrous thing to do is to ask you to sleep over since I was partly to blame.” She said, “Sure, but do we have to sleep? We still have a few toys to try....” And with that we moved to my room.