A few years ago I was working a job where I had a lot of down time. I would work long hours, often late into the night but many times all that would be required of me was to physically be there. I spent a lot of time sitting in my office watching movies and playing around on social media.
Mandy and I went to high school together and we ran in similar circles but had never dated or anything like that. We hadn't talked or hung out since she graduated a year ahead of me. Mandy was short with curly blonde hair and glasses. Her boobs were probably small C cups but they seemed bigger by comparison to her small overall build. She was kind of nerdy but I always thought she was cute. After graduation we didn't really hang out but we were friends on Facebook.
One night (several years after graduation), I was at work scrolling through my feed and Mandy had posted one of those questionnaires that used to float around on Facebook and had invited her friends to reply. I read through the questions and saw there were like thirty questions. They started out innocent enough with questions like 'are we friends?' and 'would you get drunk with me?' but they got progressively more suggestive. Nothing outright sexual but definitely borderline. I was single and horny at the time and had nothing better to do so I filled it out and messaged it to her. I deliberately answered the more suggestive questions with overtly suggestive and sometimes explicit responses. One of the questions was, 'would you play strip poker with me?' to which I replied, "Just tell me where and when!"
About mid morning the next day I received a message back where Mandy filled out her responses to me and noted she didn't realize how dirty this survey was and that she should read them more closely before posting. However, her responses matched my level of suggestion. I read through her answers and noted she replied to the strip poker question with, "I've never played strip poker but I'd be willing to give it a try!"
"So when are we playing strip poker? 😜," I messaged her back..
"Omg I REALLY need to proofread things more carefully before I post! 😂😂😂," Mandy replied.
"Haha no worries. I haven't played in a while so I'm probably rusty anyways! 😜" I joked, "How have you been?!"
"You're probably still better than me considering I've never played 😞. I've been good! Just working and living 🤷♀️," She answered.
"I figured you'd be married with a couple of kids by now," I messaged her.
"Lol, not yet. I was engaged but he cheated on me a month before the wedding," She said, matter-of-factly.
"OMG that's terrible! I'm sorry, I didn't mean to bring up a painful subject. What a jerk! Was this recent?" I asked.
"Don't feel bad! This was like a year ago now. It is what it is. He was a douche," Mandy answered.
"Seriously! Sounds to me like you dodged a bullet," I replied.
"Totally. He is someone else's problem now! What about you? Living the playboy life? Wild, drunken, strip poker parties? Different girl every night?" Mandy asked.
"Haha I wish! Not quite that crazy. Occasional drunken party but no strip poker. No girls currently 😞," I said, candidly.
"That's a shame!" Mandy insisted.
"Lol which part? The no girls part or the no strip poker part?" I asked.
"Lol both? Jk. The no girls part! You're a catch!" Mandy replied.
"Aw thanks! Just haven't had much opportunity to meet anybody," I explained, "Probably doesn't help that I suggest strip poker to all my first dates! Lol jk. Have you dated anyone since you broke off the engagement?"
"LMFAO! AW! Strip poker on a first date sounds like fun! 😜 And a little bit here and there. I'm on the apps as they say lol," Mandy responded.
"It does, does it? Lol soooo can WE go on a date?!" I said only half joking.
"Lol MAYBE 😜," She teased.
I had to sign off to go do actual work but Mandy and I started chatting regularly after that. She worked as an admin assistant for some real estate guy and had nothing to do a lot of the time. Since we both had a lot of downtime at our jobs we messaged a lot and eventually transitioned to texting. I continued to casually joke about our "date."
One morning Mandy was complaining about being bored because her boss was out of town and all she had to do was answer the office phone. I had worked a super early morning shift and was going to be getting off work at noon.
"Well I'm going to be home in an hour if you feel like playing hookie 😜," I texted.
"Booo why do you get to go home early?!" Mandy said, with a hint of jealousy.
"I don't, I've been at work since 3am 😴" I explained.
"Good lord, that's waaay too early!" Mandy commented.
"Eh, it happens from time to time. So what do you say?" I asked.
"What'd you have in mind? 🧐" Mandy asked, suspiciously.
"I'm always down for strip poker 😜," I replied.
"Haha you have a one track mind! I can't leave the phone unattended if an important call comes in," She said.
"So have the office phone forwarded to your cell phone," I suggested, eager to remove any obstacles.
"I have no idea how to do that," Mandy texted back.
"If you want to play hookie, I can totally tell you how to set it up," I offered.
"Well which is it? Hookie or strip poker?!" She joked.
"I say both! 😜" I answered.
I waited with nervous energy for Mandy to respond.
"Sooooo IF I was considering it, how would I set up the call forwarding?" Mandy asked.
I texted her instructions as most phones have a pretty similar set up and told her she could text me her office number and I could call to test it.
Mandy followed my instructions and texted me her office phone number. I immediately got hard when I saw that number come through, taking it to mean this was happening. I called the number.
"[boss]'s office, Mandy speaking. How can I help you?" She answered in a very professional manner.
"So? What do you think? Hookie and strip poker at my place?" I asked without announcing myself.
"Boy! You are crazy!" Mandy laughed.
"I just thought you were feeling adventurous," I teased.
"Hmmm maybe. Text me your address," Mandy said, thoughtfully.
We got off the phone and I texted her my address and said I'd have the cards ready. My shift ended and I drove home and did a quick clean up of my place. Around 1pm I got a text from Mandy saying she was outside. I went and opened the front door so she could see which house was mine.
I watched Mandy as she climbed out of her little Corolla and slung her little bag over her shoulder in such a way the strap lay between her breasts. She waved and said hi enthusiastically. She looked really cute in her work clothes, almost like Pam from the office only with dirty blonde hair. She was wearing form fitting blue jeans with a light purple cardigan over a white button down blouse with an open collar.
"Holy crap, what a blast from the past!" Mandy said as she walked up my front steps and gave me a big hug.
"I know! You look fantastic!" I replied.
I invited Mandy inside and showed her around where I lived. It was a little awkward because I wasn't exactly sure what to expect as it was the middle of a work day and we hadn't seen each other in person in like five or six years.
"So… pretty slow day at the office?" I asked as we wandered into the kitchen.
"Yeah. My boss is traveling for a conference so he isn't around to give me any work. I'm basically just an answering machine," Mandy mused.
"Sounds like my dream job!" I joked.
"Yeah, it could definitely be worse," Mandy acknowledged.
"Well I'm off work for the day so I'm gonna fix myself a drink. Can I get you anything?" I asked after a moment of awkward silence.
"I shouldn't…" Mandy said, considering.
"I thought we were being adventurous…" I replied.
"Yeah, just deciding how adventurous I want to be," Mandy laughed.
"Well how about this, if you WERE to be adventurous, what would be your drink of choice? If you don't want it you don't have to drink it," I suggested.
"What are you having?" Mandy inquired.
"Rum and coke. I have beer and vodka too," I offered.
"I'll have what you're having," Mandy decided after a moment of contemplating.
"Coming right up!" I said as I mixed our drinks.
I handed Mandy her drink and raised a toast. We clinked glasses and sipped our drinks while we stood there over the kitchen counter in another brief awkward silence.
"So what do we do now?" Mandy asked.
"I thought we were gonna play strip poker?" I teased, "I have the cards ready and everything."
"So you're serious? You want to play strip poker right now?" Mandy asked.
"I'm down if you are," I replied.
"But I don't know how to play," Mandy said as she took another sip from her glass.
"You know how the hands work, right?" I asked.
"Yeah, I mean I've played regular poker before. Just not strip poker," Mandy clarified.
"That's ok. I'll teach you. Knowing the hands is the most important part," I said as I walked past her towards the living room where I had a deck of blue bicycle playing cards laid out on the coffee table.
I sat down on the couch in front of the coffee table and Mandy sat down next to me on my right. I explained the rules as simply as I could.
"Oh… so it's just like regular poker only using clothes instead of chips?" Mandy asked.
"Exactly!" I confirmed.
"Ok I think I get it. Can we do a practice round first?" Mandy asked as she sipped her drink.
"Absolutely!" I said as I shuffled and dealt us each a hand.
"Ok so we each have to ante up with a single piece of clothing. Jewelry doesn't count. So my ante is one of my socks," I explained.
"Ok same," Mandy responded.
"Ok now since I was the dealer, it's your turn to bet. So look at your cards and decide what you want to bet," I said.
"Do I have to bet anything?" Mandy asked.
"You don't HAVE to. If you don't want to bet you can say 'check' which means you don't bet. If you check it will be my turn. If I bet my other sock, you will have to match my bet or fold. If you fold, I win the hand," I explained.
"Ok I think I got it. So I'm going to not bet anything," Mandy said as she sipped her drink.
"Ok that means it is my turn to bet so I bet my other sock. So not the bet is back to you and you can choose to call, fold, or raise," I said.
"Got it. I call," Mandy replied.
"Ok now you can choose to trade in up to three of your cards for new cards to try and make a better hand. Then we bet again," I explained.
Mandy considered her cards for a moment then selected three for discard. Then her phone rang.
"[boss]'s office, Mandy speaking. How can I help you?" She answered as she stood and wandered back towards the kitchen.
I overheard her take a message while I traded my cards and sat patiently. A moment later she was back.
"Sorry about that," She said as she sat back down and picked up her cards.
"No worries. You traded your cards and I traded mine. Now it's your turn to bet," I explained.
"Ok so I bet my sweater," Mandy said.
"Ok I call. Now turn your cards," I said.
Mandy had a pair of 8's with a queen high and I had a pair of Jacks.
"Ok so if that had been the real game, I would win both your socks and your sweater," I said.
"Ok got it," Mandy acknowledged.
"Ok ready for a real hand?" I asked.
"Let's do it!" Mandy said as she raised her glass to cheers the air before taking another sip.
By my count we each started with 7 pieces of clothing. Mandy had two socks, her jeans, her cardigan, her blouse, and her bra and panties. I had two socks, jeans, a belt, my work shirt, my t-shirt, and my underwear.
I dealt us each a hand and I had an ace high. She bet her other sock and I called. We traded in our cards and I didn't end up with anything except my high ace. Mandy didn't bet anything on her turn and neither did I. We turned over our cards and she had a pair of 2's.
"Yes!" Mandy pumped her fist, victoriously.
I pulled off my socks and dropped them in a pile on the floor next to her
I dealt us another hand. Mandy ante'd with a sock and I ante'd with my button up work shirt. She dealt us a hand. I looked at my cards and found I'd been dealt a pair of queens. I immediately got excited but tried to temper myself. I checked. Mandy felt confident and bet me two more socks. And just like that I had to choose.
"Fuck it, I call," I said knowing that if I lost I would be left with nothing but my underwear.
We both discarded three cards. I didn't get much help but I felt confident in my queens.
"I bet my underwear," I said as nervous adrenaline ran through me.
Mandy wasn't concerned. All she had to do to call was bet another sock and she did so without hesitation.
"I call," Mandy said.
I was so insanely nervous. I took a deep sip of my drink and turned my cards over. To my delight, my queens beat her pair of 10's. Mandy rolled her eyes as I celebrated. She peeled off her socks and threw them in the pile with mine.
I dealt us another hand. I ante'd with a sock and Mandy ante'd with her cardigan. I looked at my cards and all I had was a 10 high.
"Check," Mandy said when it was her turn to bet.
"Ok I bet three socks," I said knowing that if she called and lost she'd be down to just her panties.
Mandy hemmed and hawed for a minute but decided to fold.
"So I have to take off my sweater now?" Mandy asked.
"That's how the game works," I answered.
Mandy unbuttoned her cardigan and pulled her arms from the sleeves and added it to the pile of clothes on the floor.
Mandy dealt us another round of cards. I again ante'd with a sock and Mandy ante'd with her blouse. I looked at my cards and I had a pair of 4's. I bet a sock. Mandy eyed me and then called with her jeans. We traded in our cards and reviewed our final hands. I only had a pair of 4's with a 9 high but I decided to be bold. I bet two more socks which would mean that if Mandy lost she'd be naked.
Mandy considered for a moment.
"Damn it! I fold," She pouted.
My dick was so hard I had to readjust so it wouldn't cause me pain as it strained against my jeans. Mandy stood up, undid her jeans and shimmied them down her legs to the floor. Then she sat back on the couch, took a sip of her drink, and started unbuttoning her blouse as she rolled her eyes. Then she tossed her shirt to the pile. She had on a light purple bra and matching panties. I couldn't help staring at her cleavage as her C-cup boobs were slightly pushed up and together by her bra.
"I knew I'd be terrible at this game!" Mandy said in frustration.
"I think you're doing great!" I teased, "Need a refill?" I asked.
"Fuck it. Why not?" Mandy replied as she threw her hands up.
I quickly scurried to the kitchen and mixed us two more drinks while Mandy sat there in her underwear. After I gave Mandy her drink, I settled back into my seat and dealt another round. This time she had to ante with her bra. I wanted to see her boobs so bad I had to actively stop myself from shaking with nervous energy.
I looked at my cards and all I had was a jack high. Mandy checked. I bet two articles of clothing which would put her all in. I expected her to fold again but to my surprise she called. We traded in our cards and since she had nothing else to bet, we turned over our cards. To my chagrin Mandy had a pair of 7's.
"About fucking time!" Mandy sighed in relief.
I tossed her both of her socks and one of mine while she dealt another hand. She ante'd with a sock and so did I. I looked at my cards and I had a pair of 9's. I bet 2 articles of clothing. Again, to my surprise, Mandy called. We traded our cards and I ended up with a pair 9's with queen high. Not great but not terrible. I bet two more articles of clothing in the hopes that this would be the hand where she had to get naked.
"I call," Mandy said.
My heart lept when she said that. We turned over our cards and Mandy had a pair of fucking aces!
"YES!" Mandy shouted loudly enough the neighbors could have heard.
I tossed her sweater and her jeans over to the pile under her then stood and unbuttoned my shirt. I then pulled off my undershirt and balled them both up and tossed them onto her pile. I then sat back down, took a sip of my drink, and dealt another hand.
I ante'd with my belt and looked at my hand. I had a pair of 6's. Mandy and I both checked and then traded our cards and my hand didn't really improve. Mandy bet one article of clothing and I called with my jeans. If I lost there'd be no hiding my boner. We turned over our cards.
"Fuck!" I said in exasperation when Mandy showed three 8's which easily beat my hand.
"Hell yeah! Drop 'em!" Mandy said as I stood up and undid my belt.
"See you're not bad at this game at all. I'm wondering if maybe you're hustling me!" I joked as I unbuttoned the fly of my jeans and pulled them down to the floor.
My dick was at full attention making a tent in my boxer briefs. I didn't bother trying to cover it.
"It must be beginner's luck," Mandy teased.
She didn't comment on my boner. She just dealt us another hand. I had only my underwear with which to ante. I looked at my cards and I just had an ace high. Since I had nothing to bet we both checked and traded our cards. I didn't get any help and my heart sank a little with the assumption I was about to lose the game without seeing Mandy naked.
We turned over our cards and to my delight, Mandy had nothing and my ace won me back a sock.
"Yes!" I pumped my fist.
"I almost had you!" Mandy replied.
"Yeah but I'm still in this!" I said as I dealt a new hand.
We ante'd and I looked at my hand to find I had just a 9 high. Mandy bet one article of clothing.
"Fuck it," I said, "I call. I'm all in."
We exchanged our cards and the strip poker gods smiled upon me granting me another 9. Since I was all in, we turned over our cards and my 9's beat her pair of 7's
I won back two more socks! I was still alive. I leaned over and pulled them back from her pile while she dealt a new hand. We each ante'd with a sock then looked at our cards. I had a pair of 5's. I decided to bet strong to see if she would fold so I bet two articles of clothing.
"Call," Mandy answered with confidence as she took a sip of her drink.
We exchanged our cards. I discarded three and among the three cards I got back was another 5 which gave me three of a kind!
"I'm all in," I said.
"I call. I think I got you this time," Mandy said as she laid down her cards showing a pair of kings.
"Sorry, pal. Read 'em and weep," I teased as I showed my three of a kind.
"Sonofabitch!" Mandy said, flustered.
For the next two hands we just traded ante's. First she bet and I immediately folded, then I bet and she immediately folded. At the start of the game we each had seven pieces of clothing and at this point I had eight pieces and she had six, so we were pretty even.
I dealt us a new hand and we both ante'd. I checked my hand and saw I had king high. Mandy checked and when the bet came to me I bet one article of clothing and Mandy called. I drew three new cards and they were two 3's and another king, giving me two pair.
"I bet whatever you have left," I declared.
Mandy eyed me, squinting with suspicion.
"What?" I asked.
"I'm trying to decide if I think you're bluffing,” Mandy replied.
"I could be," I said with a smile.
"Fuck it. I'm calling," Mandy said.
My nerves were vibrating at this point. I turned over to show I had two pair.
"Damn it!" Mandy said as she dropped her head.
Mandy flippantly tossed her cards on the table to reveal a pair of Jacks.
"Uh oh…" I said in a playful tone.
"I assume that means I have to get naked?" Mandy asked.
"That IS how the game is played," I answered as I took a sip of my drink.
Mandy just eyed me with a raised eyebrow then stood up and pulled her underwear down to the floor. Her pubic hair was light and neatly trimmed. She sat back in her seat and I stared intently as she reached behind her back and unclasped her bra. She let the straps fall down her shoulder as she draped her arm across her chest. Then she finagled her arms out of the loops of her bra strap while continuing to cover herself. Then she managed to pull her bra out from under while leaving her arm in place, obscuring her breasts.
I gave her a puzzled look.
"What? I'm naked!" Mandy said, teasing me.
"Uh huh suuuure. We both know that's cheating," I said.
"Nuh uh," Mandy said, playfully.
"Ok… how about this… you show me yours and I'll show you mine. Deal?" I suggested.
Mandy looked at me for a moment and considered my offer, "Deal."
"But you have to go first," I added.
"Ugh fine," Mandy said as she rolled her eyes and then let her arm fall away.
I felt a wave of excitement roll over me. For some reason it's infinitely hotter to see someone you know naked and I couldn't believe Mandy was sitting right next to me, butt naked. She had fantastic boobs with stiff, light pink nipples. I couldn't help staring.
"Ok mister, you got a good look. Now it's your turn," Mandy insisted.
"Ok…" I gave in as I stood up from the couch right next to her.
My dick was fully erect and straining against the fabric on my underwear, not leaving much room for imagination.
"Ready?" I asked as I looked down at her.
Mandy just sat back with her arms and legs crossed looking up at me.
"Ready whenever you are," She said.
I slid my thumbs inside the waistband of my underwear and leaned over to pull them down to the ground. Then I stood back up with my erection on display for her. Mandy just looked at it and up at me.
"What do you think?" I asked, not sure what else to say at this moment.
"I can't believe I'm seeing [throway2016]'s penis right now," Mandy said, in a state of shock.
I stood there awkwardly for a moment while she stared.
"Do you want to touch it?" I asked.
"Just for a second," Mandy said as she leaned forward and grazed the underside of my erection with her hand.
She gently ran her finger tips along the side then she wrapped her hand around my cock. I just stood there, looking down and watching as she just kind of took it in her hand and got a feel for it.
"Do you want to suck it?" I asked.
Mandy thought for a moment then said, "Just for a second."
Mandy leaned forward and took the swollen head of my cock in her mouth. She closed her eyes and she inched my shaft deeper into her mouth. Her mouth was warm and I could feel her teasing the tip of my cock with her tongue. I took a mental snapshot in my head of this moment. Mandy was someone with whom I never thought I'd have an experience like this. She took my cock in and out of her mouth very slowly.
"You're really good at that," I told her.
"It's really big," Mandy commented before taking my cock back in her mouth.
I'm really just average but it's always fucking hot to hear a girl compliment my size. Mandy continued giving me an amazing blowjob. She stroked my shaft that was slick with her spit in rhythm with her mouth. Then she grabbed my ass with both of her hands and pulled me into her as she increased the intensity. After only a few seconds of that I started feeling like she was going to make me cum so I stopped her.
"Lay back," I whispered.
Mandy laid back against the armrest of the couch. I lowered myself on top of her and began licking and kissing her nipples. I teased them and sucked them and gave them the gentlest little nibbles. I kissed her up along her chest and neck. Then I kissed her on her lips and massaged her tongue with mine. While I kissed her, I began running my hands up and down her thighs, first on the outside then on the inside. Each time I ran my hand up her thigh I came closer and closer to her pussy. Mandy trembled when I finally touched her there. Her wetness immediately coated my finger tips as I massaged her labia apart and found her clit. As I kissed her, my hand went back and forth between gently circling her clit and massaging her opening. After a little bit of that, I started kissing down her neck and chest, between her breasts, and down her stomach and pelvis until I was able to find her clit with my tongue. I flicked my tongue up and down on Mandy's clit and let her wetness coat my chin. Simultaneously, I began sliding my index finger inside her pussy, slowly at first. I listened to her body language and increased my intensity as she started grinding her pussy against me. When she was ready I added a second finger and curled them in a 'come hither' motion to massage her G spot with each outward stroke. I moaned as I firmly tongued Mandy's clit. Then I shifted into high gear as I fervently finger fucked Mandy's pussy. I remember the rapid smacking sound of her juices with each inward stroke.
"Oh FUCK you're gonna make me cum! Don't stop!" Mandy said, breathlessly.
I continued exactly what I was doing and held on for dear life. Mandy's hips were jutting up and down as she ground her pussy against my face. Her body started to shake and I held on tight to her hip with my free hand.
"Yes! Yes! Yes!" Mandy moaned as her whole body spasmed.
Mandy draped her arm over her forehead as she came to rest. I kissed her stomach as she caught her breath.
"Do you want me to get a condom?" I asked.
"Not today," Mandy answered through deep breaths, "Sit back."
I did as I was told as Mandy pulled herself up to a seated position and swiveled her legs off the couch. Mandy leaned over to me and kissed me deeply. She put her tongue in my mouth and it played with mine. While that was happening, I felt her hand grab my cock and begin stroking me. My body tensed at her touch.
After a few seconds of making out, Mandy got down on the floor between my feet, looked up at me and said, "Tell me when you are ready to cum," then started aggressively sucking my cock.
She made a primal 'glug' sound with each downstroke as my cock hit the back of her throat. I reached down and squeezed her tits and watched in disbelief that this was actually happening.
"It's not going to take long," I warned her.
"Tell me when," Mandy insisted between strokes.
I felt my orgasm swell in me. I was passing the point of no return.
"Fuck, I'm gonna cum!" I warned her.
Mandy took my cock out of her mouth, leaned forward, and stroked me with her right hand. My cock started spurting cum all over her chest and onto the tops of my thighs. I was so turned on I produced a large amount of cum and it made a mess. Mandy licked my cock clean then smiled up at me with my cum glazing her chest.
Suddenly Mandy's phone rang.
"Oh shit. Umm…. Can you um… get me a paper towel or something?" Mandy asked.
I jumped up and ran to the kitchen with my erection awkwardly flopping around. I came right back with a full roll of paper towels and I had pulled one off for her. Mandy took the paper towel and quickly wiped her hand clean before picking up her phone.
"[boss]'s office, Mandy speaking. How can I help you?" She answered as she sat there crouched on the floor, covered in my cum.
While she took her call, I fumbled for my underwear. I found them and put them on and sat on the couch. I remember hearing her say something about faxing some documents. Mandy finished her call and then grabbed more paper towels to clean herself up with.
"I'm really glad that call didn't come in thirty seconds sooner," I laughed.
"Yeah, that would've been bad," Mandy said, amused, "That was a client who actually needs me to fax them something from our files so I have to go back to the office."
"Oh that sucks. I'm sorry you can't stay," I said, genuinely bummed.
"Eh it happens," Mandy reassured me, "We will just have to plan for a rematch!"
"I'm down to defend my crown anytime, anywhere," I joked.
Once she got most of the cum off her chest with paper towels, she asked me where the bathroom was. I showed her and she took her clothes in with her and got cleaned up. Mandy emerged fully dressed and I saw her out.
That was the beginning of a friends with benefits situation that went on for a few months between us. If you liked this story let me know. I have a few more stories with Mandy that I can type up if there is interest.
Feel free to DM if you want more details.