Stepping Out

My sister is single...again and there isn't too much worse for her than to not have someone in her life. Thats not unusual but at times she is nothing but insufferable to everyone around her too.

We were originally going to the swap meet early along with brunch on a recent Saturday, then she didn't want to do that and wanted to go shopping later on then have dinner out. I asked her is she was sure this time and with a chuckle, she said sure.

So I got ready-I put on just a touch of makeup and played with my hair to get it the way I wanted, then some bangly jewelry.

I pulled my baby blue sheer underwire bra out of the drawer and hooked it on and then I found a freshly washed pair of tan nylons which I pulled onto each foot, calf, thigh and then my butt and tummy. I'll wear nylons or capri hose under leggings and yoga pants where the material is thinner or when they are a lighter shade like white, gray creme, that sort of thing.

Looking around in my walk in, I looked at all kinds of tops and finally settled on a bright red semi sheer casual blouse with a touch of orange in it and pulled it on, buttoning it up the back. Then I went to my drawers and found a cute pair of light tan leggings with some mesh cut outs up each leg, pulled them over my nylons and looked at myself in the full length mirror. I decided to let the blouse hang loose-it was one of those that was shorter in front and a bit longer in back-it hung about halfway down my butt. Not bad! Then I rustled around in my closet again and found some brown flats to wear out shopping.

Then I waited....and waited. Well after an hour, she called and now wanted to go out for dinner then drinks and dancing. Really? At first, I wasn't so sure as she just wanted me to help her find some guy and wasn't wanting to go out by herself. I thought about it some more as she was chattering about some semi underground club in Westwood that was full of fun high end people.

So the past few weeks, I kind of knew that my husband was dating someone. We have a great relationship and we enjoy swinging and the like and we've always had an arrangement where we can have a side dating thing from time to time, but we are pretty good about telling each other and being respectful to each other about it and not keep things from each other. As often as not these playmates have often ended up being swing partners or threesomes with us all playing together too.

I wasn't pissed or angry but was irritated at him nonethless and decided to myself "what the hell", he's fucking some cute young thing, I need to do something to let him know I'm sexy and desirable to sexy, hot and good looking people too, my sister and I haven't had a fun night out together much less meeting men in a long, long time so.....I stopped her short in her monologue and said yes of course we will.

I didn't want to go back and change into a dress or anything but I re did my makeup for dinner and a night out-specificly, I rubbed the faint eye shadow off and applied gold dust and slate eyeshadow, gave myself cats eyes, made my blush darker and then applied bright red lipstick. I added more jewelry, including my thin black steel necklace that was also a casual collar.

I belted my blouse with a gold toned belt and then decided to ditch my flats and I took a pair of over the knee brown boots out of the box and put them on. they are medium brown and have a high spiky heel. I tucked my leggings into the boots.I also threw on a black leather jacket. I looked like I was on the hunt for trouble.

Debbie was wearing a very sexy very sheer gray top and bright red bra and black jeans. She decided that she didn't like the boots she was wearing and I let her borrow my snakeskin pumps. Before leaving I changed my bag to something more evening like so I grabbed my gold clutch and almost as an afterthought, remembered to put in some breath mints, another edible, a spare pair of nylons and several condoms with my other stuff in the clutch in addition to my perfume and compact.

She finally came over and we shared an edible before heading out. As we drove from our home, she was talking about how she really needed this, how she really really appreciated me going with her and how she "really owed me one". Debbie also offered to give me money to cover an uber should she meet a nice guy. I declined and told her I'd be just fine if I needed to get myself home and told her I'd let her know somehow if I thought the guy was a creep or unsafe or something like that and we agreed on a safe word she'd use if we needed to get out of there fast.

During this, I played it cool. My sister knows that my husband and I have a healthy sex life-she's caught us making love more than once but she doesn't know too much about the kinkier aspects of our life. As far as I know, she's fairly vanilla and am not wanting her to know about any of that much less that I was entertaining the idea of a hook up. If she only knew half of what my husband and I have done!

We found a cute new Thai resturant on Ventura in Woodland Hills and had a blast matching wine with Thai food.

After that, we drove her car to the club. It was definitely underground as it was located in a strip center on the second floor that was empty except for this club, a dispensary and a 24 hour donut shop. Before we got out, we gobbled the other pot brownie as the first one was starting to wear off on us.

There was the customary line with a bouncer outside. He let us in after we'd waited about 5 minutes for him to notice us and wave us in--unattached women tend to get in right after celebrities in my experience. I knew we must have looked good to him as he "had" to pat us both down rather than just do a cursory check of our handbags.

The club was large and loud and very full, even for a Saturday night. There were multiple rooms that were separate from the main dance floor and bars-some were set up with other bands and others still were meant for conversation when you didn't want the music blasting.

We found a spot at the bar where we could see and more importantly be seen and ordered 2 glasses of wine.

The club was full of pretty people of different ages, races, men, women-it was a kalidoscope of nice looking people wearing all kinds of different clothes from jeans like my sister all the way to nice cocktail wear and suits as well as sexy clubwear too.

We met several guys we danced with and who bought us drinks but the interest just wasn't there. I'd been texting my husband, letting him know we were safe and having a good time, when this guy came up and right away I knew they'd hit it off. Nice guy, I think his name was Ron or Roger or something. He and Debbie shot off to the dance floor and were having a good time together, kissing and hugging and all that so I knew that unless he turned out to have that creep factor, they'd be going somewhere togther and I'd either drive Debbie's car home or I'd Uber it and we'd figure things out Sunday. They came over and wanted to find a table, Roger found one and we went over. Turned out they wanted it so thay could make out. I was ok with the kissing and all but it was when he managed to take her bra off and was fondling her boobs that I decided to give them some relative privacy. I told them I was getting some fresh air and Debbie waved a hand at me that she understood as she was too busy sucking on Rogers face to answer me.

I wandered around the club a bit, checking out some of the other rooms and ended up in one of the "quieter" rooms looking at some fun post modern art. There was also a cigar bar where a few folks were hanging out. I liked the smell and so slowed my pace at looking at each piece more carefully when a strong melodious voice whispered in my ear "my friend thinks you are wearing white cotton panties and I think you are wearing a sexy tiger striped thong". I was in my own world and could only stutter "what"?

He repeated himself and I turned, regaining my composure answered "so you just really want to see me naked or something, right?" He blushed a bit and I told him "buy me a drink you cutie and you may find out-if you are lucky!"

He introduced himself- his name is McLean and we went off to find the nearest bar. He was tall-had to be about 6'3" or so-he was way taller than me in my boots and had long thick red hair and had an athletes build- in our conversations he told me he was a college baseball player somewhere and was working as an architect in Santa Monica. He was wearing an expensive suit with a white dress shirt and pocket square. I liked how he looked a great deal.

I looked at my phone-i hadn't heard back from my husband for a while -was he banging that bitch now in our bed or hers I thought to myself, but my sister texted a little after 11 to let know that her and her new friend were heading out to another club.....riiiiigggghhhhtttt. I knew from experience they were going to either her home or wherever her new friend lived.

Turning back to McLean, I smiled as he brought two glasses with a bottle of wine to the table he found for us. We had a drink and then he asked me to dance. I ditched my jacket as he put his hand on the small of my back to guide me. We had fun dancing several fast and slow dances and we went back to our table and drained that bottle dry. We snuggled up a bit and he kissed me lightly on my cheek then hit my lips full on. Oh he was an amazing kisser and soon we were making out. He was rubbing my back and finally fond my butt which he fondled. His arms were like steel bands and I felt like he might be a lot of fun tonite. McLean was bold and played with my boobs through my blouse. My hand sort of accidently brushed his crotch and felt a strong bulge. I grabbed it hard let go then grabbed it harder now and gave it a squeeze.

We broke apart when a scantily clad waitress asked if we wanted another bottle and he said yes. I saw McLean sneak a peak at her ass and brought him back to me with another kiss. We went back out on the dance floor and caught a few more tunes. During the last slow song his big hands found themselves on my butt while we were kissing. He slid a hand down my leggings and felt my butt through my hose. I liked that and he did too although he had a quizzical look on his face.

After the last dance ended we went back to our table but then went back into the cigar bar room. He offered me some coke which i said yes but really shouldn't have. It hit us right away. We made out more and his hands were busy down under my leggings. As we took a break and drank more wine, I asked him who won the bet. Before he could answer, I smirked and told him I wasn't wearing panties and then he asked if I wore multiple pair of pants. I giggled and told him they are ordinary nylons and he seemed surprised but then dug his hands back in and was seriously rubbing as much of my nylon clad butt with both hands it seemed and I thought he was going to stretch my leggings until they were baggy.

Ignoring the room, I unzipped his pants. I didn't pull it out but rubbed it and felt it grow hard and powerful in my hand. He groaned as I stroked him. Teasing him, I put it back in his shorts, zipped him up and told him to quit being a bad boy. His answer was to kiss me hard, pinch one of my nipples and ask if we wanted to go somewhere else. I shook my head no as I wasn't ready to go that far-yet. I quickly checked my phone and my husband had texted me back asking if we were having a good time. Good time-ha, I was having a much better time than if I were watching some guy grope and manhandle my sister and texted back. telling him "Yes having a great time-long overdue" and then in the next line "Will be very late or I may not make it home as we've had too much wine and weed tonite". He reminded me that we had a date to drive up the coast tomorrow which made me feel a bit guilty, Then I had the image of him texting me with his dick still in the whore he was fucking and I remembered why I was here in the first place.

And if I didn't need a reminder, McLean was nuzzling the back of my neck as he pinched my boobs and nips. Man he felt good. Turning back to him we kissed and i unzipped him again and was stroking him easy yet firm. Then I leaned over and kissed his cock then sucked on him briefly. I so wasn't caring who saw me bobbing on his cock by now as I wanted to fuck him, and I really mean fuck. He asked me to leave with him again and this time I nodded yes.

As McLean paid up, I looked for Debbie's car keys and realized she never gave them to me-I guess I was driving with my new friend. We walked out of the club to his car and got in. He drove a a nice Tesla. As we drove off, I saw my sisters car and wondered how her night was going and what was I thinking about when I got into a car with a virtual stranger.

Since I didn't have my sisters wheels, I paid close attention to where we were going, my fingers near my phone as well as my trusty.25 cal 2 shot handgun in my bag as we made small talk. We made it to his condo in Marina Del Rey. His building offered a nice view of the harbor and I relaxed as he definitely was genuine.

His unit was on the 4th floor and we kissed and held hands going up the elevator. Only then did he seem to notice my weding rings. I shrugged and we both laughed as we kissed.

McLean gave me a tour of his condo, not including the 3 bedrooms when we got in and ended up on his balcony with another glass of wine in my hand looking at the boats in the marina and listening to the sounds of the parties people were having on them. Soon we were necking again-can't get enough of that mans mouth. I grabbed his cock through his pants, unzipping him quickly, pulling it out and stroking it slowly. McLean pushed me down by his shoulders although I really didn't need him forcing me. Gazing at it in the dim light McLeans cock was circumcised, long and crooked to the left with a super huge head. His balls were thick with a bit of red hair. I started sucking on him right away. Then I kissed it all over as he moaned then kissed and sucked on his balls as he moaned and said my name. I went back to the head and sucked on it while I jerked his meat. He groaned loud enough now that I thought some of the party people would have heard him, not that I cared.

Just then I thought I heard sounds behind him and in front of me. I couldn't see through McLean and I wasn't about to stop after teasing him in the club so bad. I kept sucking and bobbing and kissing and squeezing his balls for no more than 5 more minutes before he screamed my name, grunted and shot off in my mouth as I kept bobbing then stopped to take it all in. His warm seed filled my mouth and I gagged as I swallowed it all down my throat. Leaving his snake out I stood up and we kissed, letting him taste a bit of what I'd swallowed. His hands ran down my butt and into my leggings again when he sighed and told me "I really love how your butt feels-so fucking firm and smooth."

And that gave me an idea.

We silently watched the boats and partiers for a few minutes when he offered me another line of coke which I accepted. We both got high again and I told him I needed to go use the restroom. He walked me into his bedroom which was tastefully decorated except he had multiple full length mirrors which seemed a bit out of place. His room hada huge bed which had to be custom made and showed me where the bathroom was.

In my haze, I decided to be a temptress. I took my jacket off, then unbuttoned my blouse, took it off then reached back, unhooked my bra and set that on my growing pile of clothes. Thinking fast, I unzipped my over the knee boots, took them off, rubbed my feet, rolled my leggings off and put then with the rest of my clothes, leaving my pantyhose on for my new admirer.

I put my boots back on, zipped them up and then threw my leather jacket back on and opened the door. McLean had put on some smooth jazz and was lying on his bed, naked-like I wanted him. Coming over he took in my outfit and smiled at me. I fell into his arms and we necked and played with each other. Without asking me, he tore my nylons and wanted to fuck. I grabbed one of the condoms I brought with me and waved it at him. McLean was disappointed but I'd told him he had to wear one and he agreed. He tore it open and I rolled it on his pole. Pushing me down, he took me missionary. He fingered my clit as he pushed into me and as I adjusted myself to take him in, he slid the rest of the way. "Oh fuck" McLean moaned as his cock filled me up and I bit his neck, feeling the heat of his body pressed onto me.

He held me down by my wrists and thrust in and out of me. I pushed down and up, raising my hips around his and with my legs on his back and my heels digging into his butt, thrashing about as he forced his dick so far into me, he was fucking deep into me, root deep almost immediately and I felt I was losing my mind in lust. He rolled me over and wanted doggie. I buried my face into his blanket as he found my cunt again and poked his hard throbbing meat hard into me, grabbing my arms and and constraining me with a firm arm bar.I came first after maybe 20 strokes and I smiled to myself and screamed into the blanket. McLean didn't stop, smoothly pistoning in and out of my very slick twat, letting loose of my arms and holding onto my hips as he fucked me. I heard a sound in front of me again and as I got up on my hands I saw faintly hairy legs then a hard cock.

"Hold on here-what ths fuck is going on!" I fairly screamed,

wishing I hadn't left my bag and clothes in the bathroom earlier.

"Um well, I'm Ben, McLean's roomate."

"Hi Ben, McLean didn't tell me he had a roomate."

"Yeah, he can forget little things like that."

"So Ben, were you watching us on the balcony?"

"Yes that was me. As soon as I saw you both I went back to my room."

"So Ben, what are you doing in here now?"

" I thought McLean might need some help with a cute thing like you."

Ben was blonde with deep brown soulful eyes and a faint beard. He was shorter and stockier than McLean with a powerful build. All the while we were talking, McLean had slowed down his pace without stopping and had reached around and was rubbing my clitty. Ben was stroking himself and I grabbed it and stroked it for him laughing and breaking the ice.

McLean picked up speed again and at the same time Ben moved closer, his stick in front of my face. I know started sucking on Ben and all three of us found a solid rythm. McLean didn't or couldn't fuck me faster but he seemed to be fucking me more intensely and was muttering a string of curses skyward as we fucked. As I was blowing Ben, he grabbed my boobs and gave them some much needed attention. I was loving the spit roasting I was receiving from these two cute guys and orgasmed now-robust and full. I was savoring Ben's precum when he groaned and I felt and tasted his cum in my mouth. He hadn't cum as much as McLean and it went down my throat easily. McLean loved what was going on and I felt his balls tighen and cock get harder. It wasn't long before he blew his load into the condom. Oh wow, that was just what the doctor ordered.

We fell in a tangle and chatted a bit. Turns out Ben and McLean grew up together back east and came to California sometime after school. Ben worked as a director for a tech start up in Long Beach.

I started to get up to go put my clothes on and call an uber when Ben pulled me back to him and started kissing me. Ben was every bit the kisser McLean was and I kissed him back. He started playing with my boobs again and I about swooned. McLean got in on the act as well and played with my still tingling twat. On my back now, I was jerking them both while they played with and kissed and bit my earlobes and neck. God I was getting hot! I started blowing McLean now as I jerked Ben. Ben scooted around and was fingering me and also was licking my twat, which felt great after being fucked by McLean. I was moaning on McLean's cock as Ben expertly munched me.