Keeping Her Company, Part 14: First Day Of Work Trip

So a month later, my company sent me to Chicago for a work convention. After the first long day of the convention, I get back to my hotel kinda late. I stop by the hotel bar before going to my room. I come in, and sitting at the bar is an older Indian woman, wearing a glasses, a green blazer with matching pants, an orange blouse, and her hair tied in a bun. I take the stool one down from her and order my drink.

Feeling a little bit of inspiration from my drink, I say hello to her and find out her name is Hira. She was 58, a 5'2" short and curvy figure, from San Diego, and like me, she's also in town for the convention. We started talking and it started off with just the usual pleasantries, and getting-to-know-you-type talk. We talked about work and how our time at the convention has been so far.

Another drink in, and she started to level with me a little more.

"I can't believe I'm telling you this, but I need to get this off my chest. Even though this is a work trip, I needed to get away. Home is just a disaster. My daughter is openly defying me. My husband has been practically ignoring me... we barely talk. It's like we live together, but our lives are anything but together. I just needed the time away, but even at this convention, I feel so alone... so thank you for spending time with me tonight... I really appreciate it."

She gets up and I ask if she'd like me to escort her to her room.

"Oh, a gentleman... what a thing to find in this day and age."

I held out my arm, almost as a joke, but she took it, and we walked over to the elevator.

"You don't really have to walk me to my room, mister" she giggled.

I assured her I didn't mind as we got in the elevator. As it took a little time to get up to the 12th floor, she leaned her head against my shoulder as we waited for the doors to open. We get to the 12th and I walk her up to her room. We get to her door and I put my arms out to give her a hug, and she looks into my eyes for a minute.

"You... you're quite handsome. I have never done this before..."

Hira softly sighed, looked away, and then continued.

"...but I know what I want. At work and at this convention, I'm the boss. At home, it's always disappointment... the demure, quiet wife to a husband who is disinterested in my body. Have you ever been with an older woman, Gavin?"

I flashed a knowing grin, leaned in a kissed her.

"I have."

"Good. I need... I want physical love."

We both sensed each other's body language and came together for a kiss. Her lips were soft, but I could feel her body tremble under my touch. Her hands slowly went to my body as we slowly made out right there in the hallway. They went to my chest as her lips explored mine. I'll have to admit, I was getting excited as her hands started to slide down my chest to my waistband. Her hands briefly slide over the growing bulge.

"Oh my... I..." her words started to trail off.

"I'm sorry, I..." I started to say.

"I should at least invite you in" she said, her voice becoming more firm as she found the words.

She opened the door to her hotel room and I followed her inside. The room was a larger room than the one I book, and it came with a king-size bed and great view of the city. We sat on the edge of the bed and kissed some more. She took off her glasses and undid her hair tie, her tresses flowing down to her shoulders. I held her tenderly as her soft and wanting kisses found my lips and I returned those kisses in kind. After a few minutes she broke our kisses and laid back on the bed, as she took off the blazer. I laid down next to her, as she reached over and held me close.

"You know, I never thought myself to be the cheating type..."

"You know what you want," I told her.

Hira's nerves calmed as her hands started to slide down my body as we made out some more. Slowly, one of her hands made it to the waist band of my pants. She broke the kiss as she paused, and looked me in the eyes. She kissed me again, softly, as she started to undo the button and fly of my pants, her hand now reaching inside and softly touching me over my underwear.

"Don't get excited... I just want to feel it over your shorts, and I have to say, you must be popular with the ladies," she said with a giggle.

"Hey," I said with a smile, "that's not fair... we should both at least be in our underwear," I said as I reached for her waistband too.

"Uh uh uh," she warned playfully as she pushed my hands away.

She softly stroked my member, more tightly confined with each touch. I started to groan just a little as did this.

"Getting a little uncomfortable in there?"

She started to play with the waistband of my trunks.

"I've never gotten to play with a penis that wasn't my husband's... I bet you want me to play with yours, don't you?"

Her hand slipped into my underwear, her fingers now gripping my member. Her soft brown fingers slowly stroked me up and down. Her breathing picked up for a minute, and then she looked up at me, and gave me a long slow kiss. We held that kiss for at least a minute. Our lips then parted, she let go of my member and backed away.

"Undress for me."

"What about you?"

"Hey, I'm the boss lady... my rules tonight."

I got up and did as I was told, taking off my shirt and then my pants until I was before her in just my underwear.

"Hey! All the way off."

I slowly took down my underwear and she looked on eagerly. She caught herself becoming the unsure neophyte again as my cock jumped up from confines of my trunks. She then physically recomposed herself, straightened her back as she eyed my body with intent. She patted the area of the bed next to her.

"Lay down."

I laid down next to her as she gripped my hard cock and kissed me deeply.

"I have to see what I'm going to be working with," she said as she broke the kiss, slowly starting to stroke my manhood up again. She then leaned in, her fingers sliding up and down the underside of it.

"Mmmmmmm no foreskin... that'll be different. The head looks very... appetizing," her finger sliding down the underside sensually, before sliding back up and once again gripping my rock hard member and stroking it up and down, faster this time. My breathing got deeper as she did this. She leaned down to my ear.

"I'm anxious to have something long and hard in my mouth again... it's been too long... will you be ready for my hot lips?"

"Mmmmm yes" I murmured, the sensations of her strokes really getting there now.

"You know, I was inspired by this trip to buy new, sexy underwear for this trip and to find someone who would inspire me to dress in this clothing. You'd love to see me in my underwear, wouldn't you."

She suddenly stroked harder after she said this.

"YES!" I exclaimed, as the sensation brought me close to cumming right then and there.

She slowed down again.

"MMM you feel so hard in my hand... I bet you would feel great inside me..."

"yes..." I said, now closing my eyes as I was starting to get really close.

"And maybe I'd let you put in other places..."

She started to kiss my chest and kiss down my stomach.

"I haven't been wet like this in a long time... I wish you could see it now. My panties are getting so damp."

She moved down and off the bed, onto her knees as she kissed my thighs.

"I can't wait to feel your hands take my soaking panties off tomorrow night."

I opened my eyes as they locked on hers. She held that stare for a moment and then kissed the underside of my cock as she stroked me again, this time faster and harder than before.

"I don't want to go down on you just yet, but... I can't let you leave you... unfulfilled... after all that teasing."

"I agree!"

She leaned in again as she jacked my cock harder and harder, and started to kiss my balls lightly and sensually. It was too much for me to take.

"Oh shiiiiiiiiiiiiiit"

Hot cum shot all over my stomach and chest, as she stroked until no more spurts of cum came out and the remaining seed dripped down over her fingers.

"Mmmmmm I think we have a deal then... same time tomorrow night?" she asked as she got up to get a towel for me. She came back from the bathroom with a wash cloth and leaned down to kiss me again. She then dipped her finger on one of the small pools of semen and brought it to her lips, tasting it.

"Interesting... a different taste than I am used to."

"Different how?"

She looked at me with a grin.

"Different better."

She helped me pick up my clothes, as I got dressed. She then hugged me and gave me a long, passionate kiss.

"I have a big presentation tomorrow... it'll be a day of working hard. Be ready for me."

We said our goodbyes as I went to my hotel room and feel asleep as soon as my head hit the pillow, with dreams of what was going to come tomorrow.