Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereA few more months had passed and not much had changed. Amber and I still spent our days together at work and of course I continue to look forward to our weekly golf outings. Every evening after golf, I follow a similar pattern of thinking about Amber on the drive home. When I got home, sometimes I masturbated in the shower, imagining her doing the same. Other times, I would lie naked in bed, stroking myself while imagining her with me. But despite my regular fantasies, I never let it interfere with our friendship. There was no way I would ever mention anything to her; I was happy with our friendship and didn't want to jeopardize it.
One morning I arrived at work to find an email from one of our directors. A project that Amber and I had completed had been nominated for a design award. The company was sending the two of us to Chicago, flying up on Monday afternoon, we would go to the conference on Tuesday before flying back on Wednesday. While it would just be a short trip, Amber and I were excited to get a few days out of town at the company's expense.
On the Monday of our trip, we met up at the airport. Each of us had a small suitcase and a garment bag, which we checked and then made our way through security and to the gate. Waiting to board our flight, we chatted and passed the time. Soon it was time to board our flight and after finding our seats, we both quickly dozed off. Waking up as we began our descent, I looked out the window and wondered whose idea it was to schedule a conference in Chicago in December. Low gray clouds covered the sky, allowing only a dull light to filter through. Every surface was covered in a thick white coating of snow; tall drifts piled up, lining the streets below.
The landing was uneventful and after we disembarked, we made our way to baggage claim where we were met by the driver provided by the convention. Heading outside to the waiting car, we were hit by a stinging wind and pelted by little shards of blowing snow. We slid into the back of the car and out of the freezing cold. Shutting the door behind me, we were relieved to settle into the heated interior and took off our coats. As we thawed out and the driver got in front, he warned us that because of the weather, traffic was worse than usual and it would take a while longer to get to the hotel. He directed us to the mini-fridge where I found a bottle of sparkling wine and a couple glasses. With a chuckle, Amber and I toasted to our adventure before relaxing back into our seats.
After a couple drinks, before we knew it we were pulling up to our hotel. It was a tall high rise, your typical conference center with a large lobby and atrium. Walking inside, we made our way to the check-in desk where we found that our company had booked us into neighboring rooms. After getting our keys we discussed the most pressing issue, what to do about dinner.
We were both starving but with one look out at the frozen city beyond the windows, we lost all motivation to go out. The hotel had its own restaurant but Amber and I both found hotel bars and restaurants to be depressing. Amber suggested a low-key night in; we could save our per-diem for a nice dinner out tomorrow. So it was decided that she would head up to her room and order pizza while I went to the shopette in the lobby to get us something to drink. We both wanted to get cleaned up and then we'd meet back at my room.
Normally I'd get beer for pizza but given the wine that we already had in the car, I looked at the that selection and I realized I had forgotten to ask Amber what she wanted. Deciding that red paired better with pizza, I grabbed two bottles and made my way up the elevator and to my room at the end of the hallway. Swiping my keycard and opening the door, I turned on the light and could see the surprisingly large room before me. Tucked in past the bathroom was a king-sized bed and beyond it was a seating area. A comfortable-looking chair, a couch and a loveseat surrounded a long coffee table facing a TV on the opposite wall. The curtains were open and the lights of the snow-covered city sparkled beyond the large picture window.
Dropping my bags on the bed, I grabbed some clean clothes and made my way to the bathroom, making sure to turn up the heat as I passed the thermostat. With the drinks from the car ride already relaxing me, I got into the shower. After getting clean, I stood under the warm water. My mind drifted off to what Amber was doing but I quickly pulled my attention back; I didn't have time for that this evening. Getting out of the shower and drying off, I did my best to think of anything but Amber.
When I packed for this trip, I hadn't considered needing casual clothes to lounge in so I was forced to put on what I had planned to sleep in. I pulled on a pair of boxer shorts and some mesh gym shorts. Finally I put on a loose, long-sleeved tee shirt and hung up my towel. No sooner had I turned off the bathroom light than I heard her knock.
Opening the door, I invited Amber in. As she stepped into my room, I was struck by her transformation. I had never seen her in anything other than her usual work attire of a polo shirt and khakis. Tonight, she was standing in front of me in a loose, thin, v-necked sweatshit, which hung across her chest. Below, she was wearing a pair of pink terrycloth shorts. The soft towel-like fabric covered her shapely hips and her beautiful, full behind, which swayed with each step as she made her way into my room. Her hair still appeared a little damp and was pulled back into a loose ponytail. The breeze coming off of her as she walked past me carried a mix of the clean smells of shampoo and body wash. I watched as her bare feet walked across the carpet as she made her way to the loveseat and sat down.
Following her into the room, I asked her which bottle of wine she preferred. After she chose one, I poured two glasses and carried one to her before setting the bottle on the coffee table. Taking a sip, I settled into the high-backed chair opposite her. Bringing her glass to her lips, Amber sank back in her seat and let out a long exhale. We were both tired from a long day of traveling and relished the opportunity for some quiet relaxation as we waited for our dinner.
We made small talk as we finished our first drink and I retrieved the bottle to refill our glasses. When I stretched the bottle towards Amber, she reached her glass out to meet me. As she leaned forward, I caught a glimpse down the v-neck of her sweatshirt. My heart skipped a beat as I realized she didn't have anything on underneath; her breasts dangled loosely in her shirt.
We both sat back and continued chatting. As Amber sipped her wine, she was smiling more and was clearly relaxed. As she tilted her head back and took another deep breath, I glanced up and down her body. Her large breasts filled her seatshirt and I could just barely make out the little point of each nipple pressing into the fabric. Her shorts were bunched up around her hips exposing the full length of each luscious thighs and I could just make out the bottom of each ass cheek peeking out from underneath. Her bare feet rested on the carpet, her toes neatly painted.
My gaze was interrupted by another knock on the door. I retrieved our dinner and brought it to the coffee table. While we started to eat, I looked for something to watch on TV, settling on the Monday Night Football game. I thought about how we were just hanging out in my hotel room, drinking wine, eating pizza and watching a football game. All of this with a woman, who I considered one of my best friends but about whom I had regularly fantasized, now seated across from me in nothing but a pair of shorts and a loose sweatshirt. I felt a stirring in my pants and I suddenly felt vulnerable, protected only by a loose pair of boxer shorts and mesh gym shorts. I took a few deep breaths to slow my pulse and clear my mind.
When we were done eating, I cleared the coffee table of everything but the wine. As I moved around the room, I became aware of the fullness in my pants formed by my already semi-erect penis. I knew the swinging bulge would have been hard to miss and I did my best to turn away from Amber. By now the game was at halftime and Amber reached over to push the power button on the remote. As the TV switched off, I was surprised by the sudden quiet in the room and became acutely aware that I was now definitely feeling the effects of the drinks. Amber relaxed back in the loveseat and gazed across at me. The sudden shift in the mood felt awkward but I fought back my anxiety and returned her gaze and smiled.
Amber rolled her shoulders and streched her neck before taking a deep breath. She looked up at the ceiling and exhaled, saying to no one in particular "Ugh, I've always liked staying in hotels. There's something about the anonymity of it, being away from home and letting myself relax in a new setting that always excites me."
Hearing Amber talk about her own excitement stirred similar feelings in me. I agreed, but with the wine lightening my mood I didn't exactly measure my words appropriately, and said that staying in hotels had "always turned me on too."
I noticed Amber squinting back at me, and in a gentle, somewhat teasing manner asked, "Oh, it turns you on, huh?"
I shyly shrugged my shoulders and smiled. A grin formed on her face as she whispered, "Me too."
My head was spinning. I had spent countless evenings fantasizing about Amber. I had masturbated while thinking about her in the shower. I had lain spread out naked on my bed, stroking myself while imagining her riding on top of me. I had pictured every inch of her voluptuous body, imagined doing so many things to bring her pleasure. But all of that had always remained in my head. Here, for the first time I realized she was flirting with me and my heart pounded in my chest.
Amber broke the silence again when she spoke up, "Can I ask you something?"
Anticipating the nature of her question I said, "anything" and took another sip of my drink.
Hesitating for a second, Amber finally asked, "Do you ever get lonely?"
"Yeah, all the time."
"Well...what do you do about it? You know, being alone... being lonely?"
I gave it some thought and replied, "Well, sometimes I enjoy being alone. I like the quiet and I like the privacy. I can do whatever I want in my apartment and when I get bored, well, I can daydream for hours on end."
Still looking up at the ceiling, she said "Daydream, huh? Yeah, I do that too." As she finished her sentence I noticed one hand reach up and briefly, very gently brush across her chest. She smiled and sank a little further back.
I was surprised at how quickly all this was happening but thinking back on the day, the buildup of sexual tension had been there all along; I had simply missed it. In the airport, she chose a seat directly next to me and leaned in close to talk. On the plane, she let her arm rest against mine as she slept and while we waited for the car she stood so close to me that her arm was almost intertwined with mine. With that and the liberating effects of the wine we had consumed, we found ourselves alone in a warm hotel room, flirting with each other for the first time.
With the realization of what was happening, I felt the familiar tingle in my groin. I felt my testicles rise and the blood rush to my penis. With each throb of my pulse, I felt my erection building. My loose boxers and gym shorts provided no resistance as a tent formed at the front of my pants. Emboldened by our continued flirtation, I made no effort to hide my erection. Amber glanced down and as her eyes settled on my groin, a smile formed on her face, she bit her lower lip and brought her hand back to her chest. As she rubbed her breast through her shirt, she sighed.
There was no need for any awkward discussion. We each knew what we wanted; we knew the other person wanted the same and we let it happen. Amber continued to lightly stroke her nipples through the fabric of her sweatshirt. As she did this, she spread her legs a little. My eyes followed up her legs, her pale thighs disappearing into her shorts, which hung loosely between her legs allowing me to see her white cotton panties underneath.
To this point, the room had been brightly lit. I reached to the side and shut off the floor lamp next to me. The only light was now coming from a single, dim lamp on the end table next to the bed behind me. As the light went down, Amber reached her left hand up the front of her sweatshirt and massaged her breasts as her right hand rubbed the front of her thighs.
Taking in the sight before me, I leaned back, spread my legs some and rubbed my own thighs. We made eye contact and Amber just nodded her head, encouraging me to continue. As I settled back and spread my legs some more, my erection became more pronounced beneath my shorts. As I allowed my fingers to cheat down and tease the inside of each leg, I felt my penis quiver and I let out a little moan.
Locking her eyes on mine, Amber continued to cup her breast in her left hand as her right hand slipped down the front of her shorts, teasing herself from the outside of her panties. Still gazing across the room at me, she allowed her fingertips to wander. Reaching down, her fingers slid their way up and down the smooth fabric of her panties. As her fingertips brushed over her clitoris, her eyes narrowed then twitched as she let out a long moan.
Following Amber's lead, I brushed my fingertips on either side of my groin, following the sensitive crease at the top of my legs. As I felt the tension building, I could feel my throbbing erection, having worked its way through the loose flap at the front of my boxers. I slowly rotated my hips, quietly moaning at the feeling of my erect penis rubbing against the cool, silky fabric of my athletic shorts. Bringing my hand back to my shorts, I finally allowed my fingertips to brush up the underside of my penis. As I felt a wave of pleasure wash over me, I tilted my head back, felt the tingling rush from head to toe and moaned, "Oh fuck... Amber..."
I looked back to her just in time to see her reach down, grab the bottom of her sweatshirt and begin to work it up. Soon, her bare breasts flopped out of the bottom of her shirt and she pulled it up over her head and tossed it aside. In the warm glow of the room, I saw her seated before me, one hand gently rubbing her bare chest, the other rested between her legs.
Her breasts were exactly as I had always imagined. They were large, hanging at her chest. The skin was pale white and smooth. Each breast had a large areola and a perky little nipple. By this time, her areola were slightly puffy and her nipples were fully erect.
Taking off my own shirt, I tossed it onto the bed behind me and continued to tease the underside of my penis through the fabric of my shorts. Then with my hand still on the outside, I slowly wrapped my fingers around my erection and moaned, "ughhh Amber, if you only knew how many time I've done this while thinking about you."
Thankfully, sparing me any potential embarassment, she replied almost immediately. Rubbing her herself over her panties she said between breaths, "ohhhhhh, me too. Oh yes... I can feel myself getting wet already. Please, keep talking."
Looking across the room, I saw her gently teasing the outside of her panties as I held my erection in my hand through my pants. I began to tell her about the first time I masturbated while thinking about her. I told her how I stood in my darkened, steamy shower and got aroused just thinking about her bathing herself. I told her how imaging her naked body got me so hard. I told her how I imagined watching her get herself off while I did the same.
As I talked, I slowly rocked my hips back and forth, stimulating my penis against my pants. I watched as Amber reached down and pulled off her shorts, allowing them to fall at her ankles before kicking them aside. Settling back into her place, she spread her legs, a noticeable wet spot forming towards the bottom of her panties.
I continued to slowly stroke myself through my shorts as I watched Amber carress her chest and tease herself through her panties. Looking back at me she asked, "Would you believe me if I told you I do the same?" I asked her to tell me more.
She told me how she likes to get home from work and close all her blinds. With the house darkened and in complete privacy, she strips down naked in her living room. She explained that with the feeling of the air against her naked body, she can always get arroused just by walking around with no clothes on. The image that that placed in my mind caused me penis to tense and I had to stop touching myself to calm my mind.
Amber then described how she likes to take long, hot showers while thinking about me. She told of how she likes to get herself worked up, imaging me in my own shower with a throbbing hard-on, stroking myself to orgasm. She explains that sometimes she can make herself cum in the shower but usually she has to move to her bed to finish herself off.
As she talked, I let my right hand slip inside my waist band. I felt my hand slowly wrap around the bare skin of my erection, the underside of the head already slick with pre-cum. Seeing me reach inside my pants, Amber did the same. Her hand slipped inside her panties and worked its way down. As her fingertips brushed directly against her clitoris for the first time, she shook and let out a long moaning exhale. I watched as the wet spot darkened and grew.
Finally seeing in front of me what I had fantasized about for so long, I was overcome with excitement. As my pulse raced and breathing got faster, I lifted my hips and used both hands to pull down my shorts and boxers in one quick motion. Letting them fall to the floor, I fell back in the chair, my hands on each arm rest. With my bare ass and scrotum lying directly on the chair, I spread my legs again, my erect penis standing straight up, bouncing slightly with each heartbeat.
Amber watched me with one hand still down the front of her panties. At the sight of my erection standing rigid, she shifted her hips and used the other hand to peel off her panties. I watched intently as she finished pulling them off her ankles. Amber must have noticed I was watching because she proceeded to ball them up and toss them in my direction.
I caught the white cotton panties as they tumbled through the air and watched as Amber sat back and spread her legs wide. Shifting her butt, she pulled her feet up onto the loveseat. Her feet rested on the edge of the cushions as her legs fell open. Her soft pale ass was pressed into the cushion and spread out beneath her. My eyes followed her thick thighs with their impeccable pale skin all the way up. There, on the mound above her groin was a patch of perfectly trimmed black pubic hair. Her thick outer lips were engorged and her thin inner lips peeked out.
With one smooth motion, she reached between her legs and lightly ran two fingers up her labia. A drop of clear fluid had formed at her vagina and she used her fingers to spread it around. Her lips now glistened as she began touching her clitoris again. All the while, she never took her eyes off of me.
I held Amber's eye contact as I again wrapped my right hand around my shaft. Then bringing her panties up to my face I took a deep breath. Her musky scent was intoxicating and I moaned as began to slowly stroke myself. Running my finger over the crotch of her panties, I could feel the slick, slippery spot that once rested against her vagina. Taking one more deep breath, I let the panties fall beside me as I continued to slowly stroked myself. As a bead of precum dripped down my shaft, I used it to lubricate my hand.
With our eyes locked on each other, we masturbated, each of us realizing our fantasies were coming true. As Amber worked her clitoris in circles, she gradually picked up the pace. Soon, I could hear the distinct slopping sound as her fingers worked away while the wetness built between her lips.