Like many people, I’ve always been enraptured with the holiday season. From late October (I consider Halloween, my favorite holiday, to be the start of the season) until New Year’s Eve, the world changes – both physically with the onslaught of decorations and lights, and metaphysically as we’re reminded of the good things in the world to celebrate. I grew up in a household that lived for the holidays, with box upon box of decorations to pull out and douse the house in (though we were more conservative about lights). I always remarked on how empty the house felt in January.

But the holidays can be a stressful time for people, as well. It isn’t just the madness of shopping for presents, packing in holiday parties and get-togethers or trying to work out travel plans. While we may enjoy the comfort and camaraderie of reuniting with friends and family, this time can be sad time for those without someone special in their lives to connect with. I recall several holiday seasons when I was single with no one to celebrate with on an intimate level, adding a taint of bitterness to the otherwise happy time.

On the other hand, some of my more unusual dates happened during the holiday season.

It was the weekend before Thanksgiving, and this was my first holiday season after a hard break up with a very special girlfriend. Work was slow due to the holiday season and friends were off with families and significant others, meaning I was left to my own devices with way too much down time on my hands. Saturday night was hardly wild as I sat at an Indian restaurant, waiting for Lynn (not her real name).

Lynn was an acquaintance who was at a few the social group site events I attended. I only her because of her luxurious mane of red hair that’s hard to miss, but beyond a casual “hello,” I doubt she and I ever spoke to each other. She emailed me about pictures with her in the background that I posted from a hike on the social group website. Her comments about the picture and some of the other attendees demonstrated a sense of humor was a mix of pop culture references and slightly risqué. A little encouraged by this, I continued trading emails with her. We told each other a little bit of our backgrounds and commiserated over being single for the holidays. Lynn asked if I would join her for dinner as an excuse to be out of the house because her friends and family were either tied up with holiday plans or long distance. I agreed to meet. Having arrived a little early, I felt a bit on edge, the restaurant was busier than I expected, speakers blared Bollywood music from a movie projected on the far wall, and I was drawing in more than a few “what’s with that single white guy?” looks from the regulars.

Almost on cue, the music died down as Lynn walked in. She was distinctively taller than I am with pale green eyes and her trademark red hair that cascaded down her shoulders and back. Immediately recognizing me, she ran up and gave me a crushing hug…which I wasn’t expecting. I could smell whatever shampoo she used and the distinct perfume that she didn’t skimp on. With both of us wearing several layers of clothes to combat the unusually cold November, I couldn’t quite figure out her shape. Even when she shed her long winter coat, her bulky sweater and vest left a lot to the imagination.

She settled into the chair across from me and we made small talk about our experiences with the social groups site and general frustrations with dating over a few glasses of wine and plates of painfully dry tandoori chicken. Lynn was a high school art teacher. She loved her work, but was tired of boys half her age hitting on and flirting with her. She previously worked in grade schools, but made the jump to a high school position when an opening popped up closer to her home. Unfortunately, she discovered very quickly that her penchant for tighter fitting clothes wasn’t exactly ideal when teaching high school boys.

“It’s really that tricky?” I asked.

Lynn laughed loudly, leaning her head back…which seemed a little over-the-top and raised a bit of a yellow flag in the back of my mind.

“You were a teenage boy once, right? What’s always on their hormone-soaked minds?”

“Fair point,” I replied. “I had a crush on an English teacher who was right out of grad school.”

“But did you ever tell her that you wanted to grab her boobs?”

I smirked. “I can’t say I ever made that bold a statement to her.”

“Some say those kinds of things to me. You see this vest I’m wearing? I wear this thing all year round because of those boys. Even with loose-fitting clothes, it’s hard to hide what I have.”

“I’ll take your word for it, right now.” And not wanting to focus a conversation on her breasts on what was effectively a first date, I let that subject go.

Lynn laughed again.

We talked about the usual things – families, hobbies, little funny stories to charm and amuse, etc. Toward the end of the evening, Lynn ran off to the restroom, giving me the opportunity to check out at least her bottom half. She wore a pair of jeans that were tight enough to show off her beautifully shaped ass and wide hips, as well as her well-developed thighs and calves. I guessed that she was a runner in her past or went to a lot of spin classes. I settled the bill when she returned and made small talk for a few more minutes as we walked out to our cars. She gave me a polite hug and we went our separate ways; I piled into my car without expectation for much else.

Sunday and Monday were painfully slow, and I spent most of my day at work rereading all the major news sites to keep myself occupied. Late Monday afternoon, my phone buzzed – Lynn texted me, asking what I was up to. A little surprised to hear from her, I traded texts with her back and forth just to see where this was going. Soon enough, she said she was interested in meeting up again. I told her my only free evening that week was Wednesday since I was headed out of town Thanksgiving morning. Lynn said she was up for that and we made quick plans for another dinner date.

Wednesday night arrived and it was even colder than before, complete with predictions of possible snow overnight. Lynn mentioned a preference for Asian cuisine, so this time we met at a local Pho place that I was fond of. Her timing was impeccable, showing up just as I pulled into my parking spot. The night air was crisp and cold with heavy clouds hanging overhead. It smelled like snow was imminent.

This time, Lynn wore black leggings and a turtleneck sweater with her trademark vest on top. Her school was on holiday break this week, so she was enjoying the down time binge-watching TV and doing some early Christmas shopping. She seemed pretty relaxed with me, and the slightly naughty sense of humor she used in her emails was presenting itself in our conversation. She even made a passing comment about how she never wore that particular sweater at school, but tended to wear it on “social occasions.”

As we ate and talked, she unzipped her vest. I’m still not 100% sure she did that because it was so warm in the restaurant or to focus my attention. Either way, her turning one way or another provided brief views of her chest. Her breasts were reasonably large, even a little out of proportion to her relatively thin frame. They were perfectly round and I could only imagine anything else about them. Lynn exhibited a habit of occasionally running her fingertips along the vest’s zipper, drawing my attention from time to time, despite my best efforts to maintain eye contact no matter what.

Dinner wrapped up and we began bundling up to leave. Stepping outside, fat snowflakes drifted down to the ground, mostly melting on the sidewalks and asphalt, but just beginning to lace tree branches and bushes. We both shivered as we stood outside.

“It’s still a little early,” Lynn said.

I nodded, “I’m up for doing something, but it’s Thanksgiving Eve, I’m not sure there’s much interesting to do tonight.”

“How about a movie?” she asked.

“Is there anything worthwhile in the theaters?”

Lynn shook her head, “Not really. We…could watch something on video instead.”

“As in at your place or mine?”

“Let’s make it your place – you live alone, right?”

“Yeah…” I cautiously responded.

Lynn rolled her eyes. “I have a roommate who’s a little odd and the place is a wreck on top of that.”

Giving her the benefit of the doubt, I invited back to my place. Fortunately, my neat freak nature meant the place was in relatively good shape, though not 100% – the bed was unmade and the place was about due for a good dusting. Lynn helped herself to a self-guided tour of the place and careful inspection of my DVD collection, apparently not impressed with my “guys who like movies” collection. With a warm cup of tea to melt away the chill and piled onto opposite ends of the couch, we took turns channel surfing, but not finding much to spark our interests. We settled on whatever sitcom was on NBC and resorted to chatting or making fun of whatever was on. At some point, Lynn looked at the channel listings again and came across one of the pay channels airing Swiss Family Robinson. She immediately perked up at this.

“Oh my God! I love this movie!”

“Really?” I asked.

“No, seriously! Do you mind?”

Shaking my head no, she flipped to the channel, catching the tail end of the opening credits. I noticed that Lynn’s chatty nature quickly died down as she watched the movie, so I took her interest in it pretty seriously and tried not making too making jokes about it. In all honesty, I think the last time I watched the movie I was still a kid, but she was completely absorbed into it. I sat back, tried to relax and not think about absolutely anything else I’d rather be watching at that moment. Lynn even suggested the “movie theater” experience, so we turned off the lights, watching a cheesy Disney classic with just the cathode ray ambiance filling the room.

I caught myself growing a little bored with the movie and my mind wandering. At first, I was thinking about other movies, then about assorted things I needed to do before I hit the road in the morning, and then what work surprises may be in store for me after the holiday weekend. Soon enough, I was lost in my thoughts.

This is when Lynn jumped over to my side of the couch, curling up next to me and taking my arm that was across on the back of the couch and laid it on her, draping over one shoulder, across her chest with my hand resting by her hip. A little surprised by her forward move, I tried my best not to read into it since I figured either she was still chilled or more comfortable with being cuddly than I was at the time.

My mind was still wandering, but at least the shared body heat was keeping us comfortable as the movie crawled on. Lynn barely shifted or moved the whole time, though I needed to reposition myself once or twice. As I was absently contemplating what I wanted for breakfast the next morning, Lynn grabbed my hand. She pulled it off of her hip, slid it under her vest and on one of her breasts.

I was a bit shocked. I didn’t think for a moment that she was all interested in me like that, so I sat stock still and quiet, trying to figure out the change of events. It didn’t help that her breast felt wonderful. Besides being perfectly round, its size made it impossible for getting my whole hand on it. I could feel the slight rise where her nipple was and the lace of her bra though the turtleneck sweater. After a short while, growing a little braver, I began exploring a little – spreading my fingers wider, moving my hand around a bit to feel more of her bust. Of course, all I can really say about them is…

Lynn barely uttered a word or a sound the whole time, seemingly content to sit there as I fondled her breast and watch the movie. A few minutes later, she just as abruptly turned her head to me and planted a heavy kiss, forcing her tongue deep into my mouth. We sat there for who knows how long kissing, tongues twisting, reaching and feeling around each other. She was a better kisser than I expected, with full lips and a very nimble tongue. Lynn shifted her position to pretty much sit in my lap, still turning her head to kiss me. Feeling a bit daring, I slid back the other side of her vest and cupped her other breast with my free hand. I could feel her nipples becoming erect as I held her.

Eventually, we changed positions – Lynn laid down on the couch and I was on top in a more traditional making out session. She shed her vest to be more comfortable, and even laying down, her breasts pressed against me, too large and full to go anywhere else. I let my hands wander and felt her ass and legs, just as firm as I expected. Surprisingly, she didn’t offer much protest to my now hard cock pressing against her crotch. I nuzzled down her neck and back up to her ear to nibble and trace it with my tongue. At long last, she let out a mild but definite purr as her hands ran up and down my back.

Strangely on cue, Lynn reached down and pulled her turtleneck sweater up and over her chest, revealing her breasts and bra to me just as the Robinsons began their climatic fight with the pirates. Taking the hint, I kissed all around and over her generous cleavage, while feeling whichever breast I wasn’t engaged in with a hand. Lynn moaned as I brushed over her bra, her nipples now definitely pressing through the material. She promptly unclipped her bra from the front, both halves falling to the side and revealing their greatness to me. I went back to kissing, licking and sucking on them with my mouth, and fingering her nipple with my hand. Explosions and yelling filled the room from the movie and felt surreal as we played around on the couch. Lynn barely moved as I played with her bust and seemed a little too quiet.

I also realized that her hands were no longer running up and down my back and ass.

I pulled away a little to see what was going. Her arms hung loose on the sides, her eyes closed and face a mix of lost in the moment and clearly enjoying herself. Her mouth hung slightly open with barely audible moans and the tiniest of gasps slipping out. I continued caressing her one breast with my hand as I watched her. Slowly she eventually opened her eyes and smiled.

“Is something wrong?” she asked.

I shook my head that everything was fine.

“I’m really wet, too.” She said and closed her eyes again, then slightly spread her legs as she pushed her leggings down to show off her matching lace panties.

I slid my hand from her breast, down her completely exposed stomach and traced my fingers along the waistline of her panties. I could just make out some small tufts of reddish hair sneaking out from the sides of the panties and slid my hand inside. There was a thick patch of unkempt hair, even more fiery red than on her head. It felt just as luxurious to run my fingers through it, and could feel it moist as I delved deeper between her legs. As my fingertips found her pussy, I could tell that she probably didn’t do any grooming down there, and it felt strangely good. Lynn was definitely wet; her hair and panties were soaked. She let out a slight yelp as I began rubbing her clit, then gave a satisfied moan as I went back to kissing and nuzzling her breasts.

Lynn’s hands remained hanging off on either side as I played with her, and she barely moved to the point that I sometimes wondered if she had fallen asleep on me. I spent more time kissing and sucking on her nipples, and taking turns rubbing her clit or sliding my fingers in and out of her slick pussy. Then she’d ease out the mildest of quiet noises – almost as if to reassure me that she was there in the moment.

Just as Ernst is saying goodbye to the rest of the family at the end of the movie, Lynn seemed to recover from what must be the most sedate orgasm I ever witnessed. She closed her legs and started to curl up on the couch, my hand still trapped between her legs.

Lynn opened her eyes, pulled her leggings up, her bra and sweater back down and gingerly sat up. She planted another deep kiss on me and quietly said “Thank you.”

We got up and neatened up our clothes. Looking outside, the snow was coming down steady and just starting to coat the roads. Lynn said she wanted to head home before the snow was too bad and I walked her out to her car. Walking back in, I stood in the living room for a good five minutes, still trying to make sense of what just happened. Lynn texted later to let me know she made it home safe.

The snow amounted to no more than a “heavy dusting” so driving out of town wasn’t much of a hassle. Thanksgiving came and went without too much incident, though Lynn was very quiet. Not one single text, call or email. I was starting to write off the whole thing as an awkward fling until Saturday she texted me to say hi. We spoke on the phone on my drive home that Sunday, and kept the conversation lively but didn’t really touch on what happened the other night. She texted me later after I was home, asking if I wanted to go out again. Curious enough to see what might happen with her next, I agreed. We needed to wait until that weekend – school was back in session for her and I took on a Hail Mary work project to finish that week.

The weather warmed up enough that weekend for going to a fall festival. It was pretty late in the season with everything shifting over to Christmas, but we found one out in the wilds of rural Virginia that looked like a good time. We spent all afternoon checking out games, arts and crafts, trying a few of the rides, even unsuccessfully navigating a corn maze.

We made our rounds through the festival quickly enough that it was only mid-afternoon by the time we saw or did everything, and decided to stop at a winery on the way back. You pretty much can’t throw a stick in rural Virginia without hitting a winery or microbrewery, and decided on one of the bigger ones to camp out for a bit. We did the tastings and grabbed an outdoor table with a bottle of white wine to relax. I kept my drinking to a minimum since I was driving, and Lynn made herself welcome to the lion’s share of the wine. We laughed, told some more stories about each other and people watched. Around the time the sun began to set, a line of clouds rolled in and the temperature quickly dropped. Taking that as a sign, we stuck a cork in the half-consumed bottle and drove back to civilization Northern Virginia.

As I pulled into a parking space at Lynn’s apartment building, she asked if I wanted to hang out – tempting me with more wine and ordering a pizza. I like the idea and soon enough we were on her couch under a blanket and giving the MST3K treatment to whatever bad movies we could find. Lynn’s apartment was a little sparse, but comfortable with a few odd pictures on the walls and a kitchen that proved Lynn and her room mate weren’t big on cooking.

A little bored with the movies we flipped back and forth on, I began feeling up Lynn under the blanket. What began with my hands caressing her hips and sides as she reclined on me evolved into both hands cupping her breasts under her bulky sweater. We kissed as I slid my hands under her bra, fingers rubbing back and forth over her erect nipples. I was hard and erect, with my cock firmly pressing against her ass as she gently moved back and forth. At first, Lynn placed her hands over her breasts, feeling my hands feeling her, then drew one hand down, where I felt her unzip her jeans, followed by the rhythmic ebb and flow of her playing with herself. I grew even harder thinking about the wet red hair she was playing with.

I traded off from kissing her to chewing on her ear or nuzzling down her neck, while trying to dislodge locks of her hair without the help of my own hands. She turned her head to me and thrust her tongue into my mouth, our tongues rolling and twisting around one another. I pushed my hips against her, trying to rub my cock against her ass, while my hands rubbed, felt, cupped and explored her amply mounds.

Then, one of the bedroom doors opened and Lynn’s room mate wandered out and into the kitchen. If Lynn weren’t laying on top of me, I would’ve jumped off the couch in shock. Lynn tensed up and froze with equal alarm.

“What the Hell – ” I began.

Lynn looked over at her room mate and neither of us moved for fear of indicating what we were doing under the blanket. “Jen (also not her real name), you’ve been here the whole time?!”

“Yeah, I worked a midnight shift at the hospital.” Jen half-muttered, half-drawled. The room mate was a little younger than Lynn and pale with straight dark hair. I then realized that her room mate was decked out in nothing more than a thin t-shirt (which left nothing to the imagination as she walked past a light or the sliding door to the small balcony), and a pair of Powerpuff Girls panties that looked older than the show’s targeted audience. I half thought that if we saw her after a shower and more dressed, she would be pretty cute, instead of the bed-headed zombie scrounging for food.

Lynn looked back and me and shrugged with a “What do we do?” look on her face. I shook my head back in return, clueless as what to do next.

“Oh,” Lynn replied, “Uhm – we’re just hanging out here.”

Jen looked over at us and nodded at me, “Hey.”

“Hey,” I replied back. “Rough night?”

“Always is this time of year.”

I felt Lynn relax a bit. Jen seemed content to gnaw on whatever she found in the fridge and inhaled a tall glass of water, then casually made her way back into her bedroom. Her door slowly creaked closed behind her.

Lynn half-giggled. “I am so sorry!” she whispered. “I didn’t know she was even here. I thought she was with her boy – actually, I don’t know if she dates guys or girls…or both.”

I crooked my neck to look back at Jen’s door. “It’s okay, she looks too tired to care about what we’re doing anyway.”

Content that Jen was entombed back in her room, we cautiously returned to what we were doing before. As Lynn slid her hand between her legs, I moved my hand to join hers, feeling her hair and hand slick with her wetness. We took turns feeling her clit and pussy, but I was first to slide my finger inside her, rubbing them back and forth. This time, Lynn moaned more loudly than our first tryst, and her other hand tightened over the one I was using to explore her breasts with.

Lynn rolled over and onto her side so we could face one another, pulling off her sweater in the process. I moved my hand back into her panties as she unzipped mine and thrust her hand into my briefs and grabbed my still-hardened cock. We kissed and I moved down her neck and chest to lick and suck on her breasts as she mechanically but gently stroked me. Her moans and gasps were somewhere between what she barely uttered at my place and the louder ones she let out earlier. I made as if to kiss back up to her face, but she gently urged me to keep my mouth on her breasts.

Whatever was on the TV was quiet enough that I gradually became aware of a dull buzzing sound.

I badly wanted to look up and see what caused the noise. It was low enough to grab my attention, but not loud enough to figure out what it was or annoy me. I moved to slightly reposition myself with Lynn, and as I was able to briefly look over the back of the couch, I noticed that Jen’s door was half open. For a moment, I could see Jen on her bed, legs spread apart and a vibrator going in and out of her pussy.

 

 

 

 

 

 

 

 

 

 

 

Of course, that’s the moment Jen opened her eyes and slightly smiled as we made eye contact.

Since there wasn’t much I could do about Jen’s voyeuristic self-loving, and since Lynn was too enwrapped on what we were both doing to each other, I focused back on her. Lynn managed to pull my jeans down as well as hers, and we immediately returned to masturbating each other. Her style was a bit unrefined, but her grip was the perfect fit as she stroked my cock and fingered the tip. My fingers and palm were soaked by her juices as I alternated between playing with her clit and playing “find the G-spot” inside of her. Lynn’s nipples stood at full attention, beckoning me to suck on them, flick them with my tongue and kiss her breasts all over.

As Lynn’s moans grew slightly louder as an orgasm built up, I noticed the buzzing was louder.

It was closer.

Lynn’s eyes were closed and she was blissfully entranced in her own world of pleasure, and I sneaked a peek with one eye to see Jen standing in her doorway. With one hand she was driving her vibrator in and out of her pussy, and the other hand pulled up her t-shirt and was feeling her naked breast – all while watching us on the couch. At this point, the blanket was mostly on the floor, giving her a good view of what we were doing.

As I slid my fingers into Lynn’s pussy again, she gasped aloud, her one free hand clamping onto mine as her whole body pulsed between tense and relaxed. Quick, shallow breaths told me that Lynn was deep in the grips of an orgasm and my hand was right where she needed it. Lynn’s hand on my cock froze in place, then gently began to move back and forth again as her orgasm passed. I felt the surge inside me as my own orgasm readied to release itself.

Jen moved from the doorway to the recliner, plopping into it with one leg handing over an arm. She turned the chair to better face toward us as she played with her vibrator on her clit, then rubbing its tip just inside of her completely shaved pussy. She gently moaned, not seeming to care of her roommate noticed.

I laid back on the couch, enjoying Lynn’s attention until I felt the sudden surge, heralding my own imminent orgasm. I stood up, standing on my knees over Lynn, still griping my cock until I came hard, pumping myself all over her stomach and breasts. Meanwhile, Jen groaned out loud, her own orgasm climaxing at the same time.

Lynn finally opened her eyes and saw Jen, then looked back up at me. “Has she been there the whole time?”

“No,” Jen answered, “but I couldn’t help it. I peeked out here and saw you two. I got turned on and wanted to play.” And with that, Jen stood up, wet vibrator in hand, and marched back into her room and shut the door with a broad smile on her face.

I went to and returned from the bathroom with a warm, wet washcloth to help clean up Lynn, who looked half puzzled, half amused. She looked at me.

“That was a new one for me,” I said. I don’t think I’ve ever had someone watch me before.”

Lynn nodded. “Me too, but I think I caught her once peeking into my room when I used my toy.”

Feeling a little exposed, Lynn and I dressed and tried our best to cuddle some more, but she eventually admitted feeling more than a little self-conscious, and wanted to take a shower and rest. I took the hint, gathered my things and went home.

I tried calling and texting Lynn over the next few days without much response. I’ve never been the insecure type, so I only left her one text and one voicemail each, leaving the ball in her court to respond to me when she was ready. Nearly a week went by without a word from Lynn. Finally, that Saturday afternoon, I received an email from her. Lynn was embarrassed about Jen, claiming Jen kept teasing her and bringing up the whole event and asking if we’d give her another show again. Rather than trade impersonal emails, I called Lynn and we talked. She signed Jen on as a roommate a few months earlier when her old room mate moved out to relocate with her boyfriend. Since then, Jen exhibited some odd behavior and Lynn was more than uncomfortable about the way she acted around friends, dates and others. She didn’t even dare have family over.

And Lynn told me she was pissed at me for not saying anything about Jen while I was there and things were happening. In retrospect, I probable should have found some way to tell Jen to take back into her room, but admittedly, the turn on of someone watching us was a huge turn on. It’s one I catch myself fantasizing about doing again with a willing (and this time, knowing) partner. Needless to say, Lynn was not happy with me, and the call ended on a tense and very ambiguous note. I thought it best to give Lynn time and space to ruminate and cool down, but eventually she emailed me saying effectively “I’m done.” I don’t blame her for how she felt, but do miss her spectacular breasts.