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Tears On My Pillow

"My first encounter with "happy tears" in the bedroom"

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Author's Notes

"This is a true story and a very fond memory I recall every Christmas. Susan, if you're out there, I hope your memory of our encounters are as fond as mine."

Friday night after work there was a standing invitation to everyone to stop in at the local bar for a few drinks. Some Fridays there were two of us; others, up to fifteen of my co-workers would show up. Some evenings were short; some extended into the early hours of Saturday morning. Some evenings I would end up going home alone, but some evenings I would get company.

It was two weeks before Christmas and this was one of those evenings.

***

The four women arrived together and gathered around the tables we occupied. Terri and Joanie came fairly often and had each spent time in my bedroom on occasion. Heather came once a month, usually had one drink and then left to go home to her husband and kids. Susan had never come before, and I was surprised to see her join us.

Terri explained that Susan was now divorced and shared custody of her two girls, with her ex having them every second weekend. As a result they had managed to convince her to come along and enjoy her newly-found single freedom.

Susan was in her mid-thirties, at least ten to twelve years older than I was, and had been married almost thirteen years. At just over five feet tall with brown hair and a curvy mom body she was an attractive and appealing woman. Terri and Joanie had been urging her to get out and meet people, have a few flings, and enjoy herself. Until tonight she had declined, saying she wasn't ready.

The evening was moving along well with everyone drinking and mingling, with lots of laughs and conversations, and of course flirting. I had joined the ladies on the dance floor for a few songs and returned to the table for a drink when Susan took the seat next to me. She put her hand on my thigh and leaned in close.

"I want you to take me home tonight," she announced. "Terri and Joanie said that should I ask you."

"Did they?" I replied with a chuckle.

"Yes, they said you were just the guy I needed."

"You could have your pick of most of the guys here," I said as I gestured around the room. "Are you sure?"

"Yes," she replied with a smile.

"Then let me know when you're ready to go."

"Now," she replied.

***

On the short drive to my place she confirmed the story of her divorce and custody arrangements, telling me she was in a place of her own now and wanted to have some new experiences. I pulled into the space at my townhouse and turned off the car.

"You sure you want to come in?" I asked. "I can give you a ride home if you prefer."

"Yes," she answered as she opened her door and exited the car.

When we entered I locked the door behind us and she took a glance around.

"Nice place," she commented. "So neat and clean."

"I like it that way," I said as we took off our shoes.

I took her by the hand and led her to the bedroom, stopping to offer her the washroom. She smiled and went in as I went into the bedroom and waited for her. She put her purse on the dresser, looked at the bed and then at me, obviously unsure of what to do next.

Being a full foot taller than her I sat on the foot of the bed, took her hand and pulled her to me so she was standing between my legs. I leaned in and began kissing her chest and throat as my hands wandered her hips and ass. I felt her hands on my head and shoulder as I worked my mouth down and latched on the erect nipple poking through her shirt, getting a quiet moan as I suckled.

I brought my hands around and undid her jeans, gently tugging them down and helping steady her as she stepped out of them. I undid the buttons on her shirt and watched as she shrugged it off and removed her bra, dropping both on the floor next to us. Her breasts were nice handfuls topped with pert pink nipples and I cupped them as I sucked her nipples once more.

I pulled her on top of me on the bed and rolled us onto our sides, putting my mouth on hers and kissing her as I undid my jeans and unbuttoned my shirt. After shrugging off my clothes, including my boxers, I wrapped my arm around her and pulled her in tight to me as we resumed kissing. Her hand made its way down my torso to my hardened cock and I felt her fingers touch the tip before gliding along the swollen shaft.

"You're pretty big" she huffed. "I want you inside of me."

"Whenever you're ready," I whispered back.

"Oh, I'm ready," she assured me.

"Get on top of me," I suggested.

She moved away and straddled me, looking at my cock in her hand before lowering herself down.

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"You are much bigger than my ex," she said in a serious tone.

"Just relax and take your time," I whispered.

"I've only had one other lover," she admitted. "That was my ex-husband."

"Don't think," I replied. "Just enjoy it."

She quivered as she lowered herself onto me, slowly taking me inside inch by inch until she had the full length enveloped. With slow movements she ground on me, hands on her thighs as she sat upright. I cupped her breasts and she groaned loudly, shuddered and suddenly became still.

Tears flowed down her face as she burst out crying.

"Are you okay?" I asked with concern.

"Oh, yes," she assured me as her hands wiped her eyes. "These are happy tears."

"Are you sure?"

She started laughing as tears streamed down her face.

"I'm sorry," she blurted out. "It's just... it felt so different, so good. I've never had an orgasm during intercourse before... and It's been so long since I was with someone... and it just..."

I pulled her down and let her rest her head on my chest, feeling the wet droplets as she sobbed. My fingers stroked her hair as I held her close and let her emotions run their course. She sniffled a few times and turned her face up towards mine.

"I'm so sorry," she apologized sadly. "I've ruined everything."

"No, no you haven't," I assured her. "Actually, I feel very flattered."

"Really?"

"Yes, really,"

I began moving my hips and my still-hard cock pushed against her opening. She gave me a huge grin, sat up and took me inside once more. Again she moved slowly, grinding into me with her hands on my chest as she fucked me. I leaned up and suckled the nipples on her swaying breasts, one after the other as she moaned quietly. I pumped my hips a few times, thrusting into her and getting deep groans in return. I felt her tighten up and begin quivering again as I pumped into her, knowing she was close to climax as my tip slammed against her cervix.

She let out a loud cry and shook vigorously as the climax hit her, her hands digging into my chest as the powerful orgasm washed through her. Once again she stopped moving and began crying, dropping down onto my chest and releasing my swollen cock into the cool air.

"Oh... I'm sorry," she giggled as the tears flowed down her face. "That's just so... unbelievable."

I chuckled as I stroked her hair once more.

"Don't worry," I assured her. "I want to please you."

"Oh, you are doing one hell of a job," she laughed as she wiped the tears away.

We laughed and cuddled for a few minutes before I rolled her off me and onto her back. I moved between her legs and pushed myself into her slowly, feeling her accept me easily this time. We kissed as we slowly fucked for a few minutes. I pulled myself up and pushed deep inside before grabbing her ankles and lifted them so they were touching. She groaned loudly as I fucked her hard, slamming myself into her faster and faster as the pressure built up.

"Oh, fuck, I'm going to cum," I huffed.

"Me too!" she squealed loudly.

She arched her back and let out a deep, guttural groan at the same time I did, her orgasm matching mine as I erupted inside of her. My body shook as I pumped my load into her, spurt after spurt as I held her ankles tight with my thighs pressed tightly against her. Tears streamed down her face as she smiled at me, rolling her head side to side as another powerful orgasm washed through her.

I let her legs down and lay on top of her, supporting my weight on my elbows as I began to kiss away the tears on her still-smiling face. She held my head tightly and kissed me deeply for almost a full minute before releasing her grip.

"Oh, you are so wonderful," she cooed.

"Thank you," I replied. "I'm enjoying myself, too."

We kissed a few times before I moved off and spooned her, pulling the covers over us before draping my arm over her waist and cupping her breast in my hand as I cuddled up to her. She let out a deep sigh, the remaining tears running onto my pillow as she fell asleep.

***

Over the next three months we spent numerous nights together, her tears replaced with loud groans and dirty talk as she learned to enjoy herself fully. In time she began dating and our casual relationship came to an end, leaving me with a tear-stained pillow, a great memory and the experience of knowing how to handle "happy tears" in the future.

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Written by 1meanjean
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