The Widow's Friend

I've always had relationship "issues". Never really had a relationship last more than a few months and usually saw a couple women at the same time. I guess I've just always enjoyed the newness part of relationships...mostly the new sex. I guess that's why a few of my friends were surprised when I decided to settle down and get married.

I'd like to think when I got married I really thought that would be it, one woman for the rest of my life. It really didn't take all that long for that theory to go out the window.

Around the time I was getting married, a good buddy of mine, Sam, was killed in Afghanistan. We'd come into the military together and spent most of our time in the same Company. Outside of work, I spent a lot of time with Sam and his wife Jenna. Mostly bar hopping and drinking too much. Usually ending up with Jenna trying to find me a wife and then taking care of our drunk asses.

About the time Sam and Jenna started having kids is when I met my would be wife. Needless to say the bar hopping party days were behind us.

Following Sam's death, Jenna and I regularly got lunch to catch up on life, kids, and family. It took a while after Sam was killed but eventually Jenna started going out again. About this time, Jenna and I were catching up over lunch when I told her my wife was heading out of town for a business conference.

"Friday night! We're going out like old times!" Jenna commanded.

"Works for me." I replied.

Friday afternoon Jenna sent me a text letting me know she had a last minute friend come into town and she'd be joining us.

We decided to meet at Outback for dinner before heading to a small Irish pub where Jenna had been hanging out. I arrived at the restaurant first which is no surprise as Jenna is ALWAYS late. I notice Jenna and her friend as they enter the restaurant and wave them over. The friend is cute! She's short with some sexy curves, black hair to go along with what I guess to be a Persian heritage. She's wearing some tight jeans and a sexy purple top.

After a quick hug with Jenna, she introduces me to her friend. "Scott, this is Shelly. Shelly, Scott."

"Welcome" I said as we shook hands. That's when I first noticed her eyes. Deep, dark, sexy eyes.

Jenna and Shelly sat down across from me. Turns out Shelly was a 24 year old flight attendant out of Atlanta and was supposed to be in town to meet her boyfriend who was stationed at Bragg. Evidently the boyfriend had found another girl and failed to tell Shelly until after she'd arrived for the weekend. Shelly and Jenna had met through that same boyfriend a while back and hung out a few times so Shelly decided to give Jenna a call in hopes of still having a good weekend.

I tend to be sarcastic smart ass and sometimes that doesn't come across well with thin-skinned people. Luckily, Shelly was not thin-skinned gave as good as she got. There isn't much I find more sexy than a sexy lady with a sharp tongue. The three of us ended up having a really great dinner poking fun at each other. I wasn't sure but throughout the dinner Shelly seemed to shoot me a few extra smiles and sexy glances as we ate. I decided I'd press the issue when we got to the pub.

After we finished eating, I followed the ladies on the short drive over to the pub. I made sure to take a much better look at Shelly's body as we made our way across the parking lot. Shelly was about 5'4", 5'5" had a shapely ass and hips with what looked like a nice set of firm B cup tits. Her hair was now up in a ponytail and showed off a sexy neckline. Shelly have me a very sly smile as I held the door for the ladies as we entered the pub. Pretty sure she noticed my staring.

The pub was smaller than it looked from the outside. It was decorated like the average Irish pub with a lot of Irish flags, Irish colors, and four leaf clovers. There was a cover band playing at the far end with the bar set up along the left side. It was still a little early so we were able to find an open table at the near end of bar where it wasn't nearly as loud.

I told the ladies I had the first round and asked what they wanted. "I'll take a water so I'm hydrated enough to take care of your dumbass later." came Jenna's reply.

"Guinness" Shelly said matter-of-factly.

"Nice choice. Be right back." I said. I returned a few minutes later to find Jenna had run off to say hi to some friends so I set her water on the table and handed Shelly her beer.

"Thanks!" Shelly said as she took a swing of her beer.

"Just glad you picked a good beer." I said.

"Yeah, well were doing shots when I buy the next round." Shelly informed me.

"Hey now. Don't be thinking you can get me drunk and take advantage of me." I replied.

"Well I do what I want so..." came her response as she stared at me with those sexy eyes, smiled, and took another long drink of her beer.

I guess my impressions at dinner weren't off the mark! I just shook my head and drank most of the rest of me beer while I stared back.

About this time Jenna made her way back to the table. We chatted for a bit longer as Shelly and I finished our beers.

"Be right back." Shelly stated as she turned for the bar.

She returned shortly holding 4 shot glasses filled with tequila. "Drink up, Bitch." She said as she placed two of the shots in front of me. Jenna thought this was hilarious as she knew I hated tequila.

"I don't like you right now." I told Shelly as I downed the first shot followed quickly the second and then a chaser of Jenna's water.

Shelly just stared at me with what I could only take as the "I want to fuck you" look in her eyes as she downed her shots. I'd had a pretty good erection up until this point but holy fuck did that look make me hard!

"Guess it's my turn." I said as I turned for the bar to get a couple more Guinness.

When I returned, Jenna had wondered off again. "Are you aware of how fucking hot you are?" I said as I handed Shelly her beer.

"I try. I'm just glad the feeling is mutual." She teased.

Our back and forth banter continued for another hour or so while we worked our way through a few more rounds. Jenna bounced around the bar talking to a variety of people occasionally swinging by the table to check on us.

Eventually, Jenna came back to see if we were ready to go so she could get the babysitter home before it was too late. Shelly and I had no objection as we were both wanting to get to a more private location.

We made our way out to Jenna's car where I sat in the passenger seat and Shelly sat behind me. Shelly wasted no time reaching around the right side of my seat to rub my arm on the way home. You wouldn't think that would be all that erotic but considering it was the first of any sustained contact, it was hot as fuck.

We made it back to Jenna's house before too long. As we entered the house, Jenna went to wake the sitter to take her home and I headed to the bathroom to offload some of the alcohol I'd had earlier. I came out to an empty living room so I had a seat on the couch and turned the TV on. Shortly after, Shelly appeared in scrub pants and a t-shirt and sat on the other end of the couch from me. We waited and watched TV while Jenna checked on the kids. It wasn't long before Jenna left to take the sitter home.

As soon we heard the garage door shut, Shelly laid across the couch on her right side, putting her head in my lap. I reached over to start massaging her hip and thigh. She moaned in approval so I worked my hand down to her stomach, underneath her shirt. Shelly quickly changed to laying on her back. I continued to rub her stomach, slowly moving my hand south. Shelly slid her right leg over so it was hanging over the edge of the couch as my hand made it's way between her legs, gently rubbing pussy her lips through her scrub bottoms. Shelly reached down, untied her scrubs, and slid them down to her knees.

I could feel how moist she was through her scrub bottoms but when I started rubbing those bare lips her juices started flowing! As I slowly slid a finger inside her, shelly moaned loudly, arching her back in approval. I could see how wet she was as I worked my finger in and out of her and just had to taste her.

I slid my legs out from under her head while I leaned down trading my hand for my mouth. I layed on my left side kind of wedging myself between Shelly and the back of the couch and used my right hand to spread those gorgeous, wet lips while I flicked her clit with my tongue. After running my tongue up and down her pussy a few times, I felt Shelly start to undo my belt and pants freeing my rock hard cock. I continued to slowly slide my finger in and out of Shelly while I watched as she took my in her mouth. God her mouth felt good!

We were just starting to get into a rhythm when we heard the garage door start to open as Jenna was pulling into the garage. We quickly pulled up our pants and sat back at opposite ends of the couch. Jenna came in a laid down on the other couch. We all chatted for a bit while we watched some cooking show. Jenna was soon fast asleep. I was supposed to be sleeping in the bonus room upstairs so I whispered to Shelly to follow me up there a few minutes after I went up.

The bonus room was a fair sized room with just a queen sized bed and night stand. I quickly got naked and laid on the bed waiting for Shelly. It wasn't long before she made her way up the stairs. She made her way over to the bed with a big, sexy smile on her face. She climbed on top of me, crawling up so we were face to face. We spent a minute or so in a hot makeout session before I rolled her onto her back and pulled off her scrub bottoms exposing that delicious pussy. Shelly's legs were hanging over the edge of the bed so I sat on the floor and proceeded to run my tongue up and down her pussy. Now that we were away from Jenna, Shelly was noticeably louder. I looked up just in time to see her pull her shirt up over her head allowing be to see her breasts for the first time. They were nice firm looking B/C cups with big erect nipples. I watched as she played with her nipples in rhythm to me licking and sucking on her swollen clit.

"Fuck, you taste good" I said.

"God, you're good at that" Was her reply .

I spent the next couple minutes slowly running my tongue up and down her wet lips, moving my tongue deeper with each stroke, pausing at the top to give her clit the attention it deserved. It was impressive how much wetter Shelly became over those few minutes.

"Fuck me. I need you inside me now." Shelly begged.

I looked up to see her watching me eat her wet pussy, resting on one elbow while still working her nipples. "Not until you cum." I replied with a grin.

The glare I got in return was a mix of "I will cut you" and "holy fuck that's hot". As Shelly laid her head back on the bed, I slid a finger inside her.

"Oh fuck yes!" Shelly let out as I started massaging her G-spot in rhythm to sucking on her clit.

Her breathing really started to pick up as her moaning got louder. Shelly reached down and grabbed my head, forcing my face hard into her pussy. I pushed my finger as far in as I could in unison. Evidently, that was the tipping point for Shelly.

"Oh fuck! I'm cumming!" Shelly cried. I, of course, hardly heard this due to her legs closing tightly around my head. To this day, it was probably the longest orgasm I've ever given. Shelly bucked and heaved with my head between her legs as I continued to work my finger on her G-spot, my face getting covered as the juices flowed from her sweet, wet pussy.

Finally, her legs relaxed from around my head and her hand that had been holding my face so hard against her pussy was now pushing me away as the over-sensation set in. As I got up from between her legs, I took in how incredibly sexy she was laying there recovering from her orgasm. One hand on her stomach, rising and falling with each breath, the other stretched over her head, eyes closed.

"My god, I've never had an orgasm like that before. That was incredible."

"It was pretty fucking hot. Glad you enjoyed it" I replied as I leaned in to kiss her.

Shelly eagerly kissed me back, obviously enjoying tasting herself. I felt her reach down and start stroking my rock hard cock, guiding it to her pussy as we continued kissing.

"Oh fuck!" I let out as I pushed deep inside her wet, tight pussy. I was pretty sure I wasn't going to last long in that position. "Damn you feel incredible! I'm not lasting long like this." I said as I slip out of her and laid on my back on the bed.

Shelly eagerly climbed on top of me, quickly lowering herself on my cock. Once I was buried inside her, Shelly started rocking back and forth, her hands on my chest. Fuck she felt good slowly grinding on my cock. I reached up with both hands, rolling and pinching her nipples with my thumb and forefinger.

Shelly must have realized her hair was hanging in my face because she leaned back and used a hair tie to put it a ponytail. Fuck she looked hot grinding my cock while putting her hair up!

As soon as she finished with her ponytail, Shelly really picked up the pace starting to ride me as she leaned back with her hands on my legs behind her. I had never had a woman ride me like that before. Her head was back, tits thrust up in the air, bouncing in rhythm. I'm pretty sure I would've cum right then if she hadn't beat me to it. Shelly suddenly leaned forward over me, hands grabbing the headboard above me, her body convulsing around my cock.

As her orgasm subsided, Shelly collapsed on my chest, breathing heavy. "I want another one of those!" She said as she started riding me again.

"Better not take long as I'm not going to make it much longer."

She just grinned at me as she continued riding me, ponytail and tits bouncing everywhere. Fuck she felt good! I knew I was approaching the point of no return so I reached down and grabbed Shelly's tight little ass, held her up, and started fucking her hard from below. Evidently that hit the spot for her as well as Shelly again grabbed the headboard as I felt her whole body contract, her pussy squeezing tight around my cock sending me over the edge. I exploded deep inside Shelly, shooting load after load into her wet pussy as it continued to squeeze my cock.

We laid there for a bit before Shelly got up, got dressed, and headed downstairs. I'm pretty sure I was asleep before she got to the bottom of the stairs. We all got breakfast in the morning like nothing happened. I'd like to say we exchanged numbers and fucked each others brains out whenever she was in town but truth is...we didn't and I never saw her again.