Role Play to Reality [FM] (Long)

My boyfriend Jake had a business trip down south and I decided to take a few days off and relax in the sun while he networked and played golf. I arrived late Thursday night and planned to spend Friday and Saturday with him, but it being a business trip, he had booked himself solid through the weekend and left only Saturday night for me.

So, Saturday night comes and Jake arrives back at the hotel tired from drinking and golf and wanted to hang out for the evening and order room service. I was like a caged animal and wanted to go out. I had been very forward with him about going out and he had promised. We had talked about spicing up our sex life. We tried light bondage, I bought a vibrator, which I think intimidates him, and we talk about role playing. He wanted to do the naughty school girl/professor and I wanted him to pick me up in a bar. I told him that I didn’t even need dinner, I just wanted him to pick me up at the bar and have his way with me that night. After going back and forth for a few minutes, he finally relented and agreed to doing the role play.

He hopped in the shower as I finished getting ready. I was wearing a little form fitting black dress that wasn’t too tight and a thong. My breasts are firm B’s and no bra in that dress drove Jake crazy. He came out of the shower wrapped in a towel and saw me putting on my heals and gave me the up and down with a “wow”. After putting on my heals, I walked over to him and gave him a kiss and told him that he better have his A game if he wanted to get me back in the room. He laughed and told me that he would see me in a bit

I walked into the bar. It was dark and a lot of wood and brass. There was a couple sitting in the middle and a few of the booths were taken. I walked past the couple and grabbed a seat at the other end of the bar. I ordered my usual, vodka and soda with a splash of cranberry. I looked around as the bartender was making my drink and in one of the booths were three men. Two younger men around my age and an older man, who seemed to be their boss. I smiled their way as the bartender served me my drink and thought they didn’t notice. The drink was strong, but not rocket fuel and it went down smoothly. I drank it most of it, when out of the corner of my eye, I noticed the men in the booth leaving. The younger ones walked out leaving the older gentleman who approached the bar to pay his tab. He was tan and with greying dark hair and was casually dressed, nice slacks, loafers, and an untucked oxford. He came up next to me and began making small talk while waiting for the bartender to finish with another patron. When the bartender came over, he ordered another scotch and told the bartender to fill my glass as well. I smiled and thanked him as he settled on the stool next to me.

He introduced himself and I did the same and told him that I was waiting for a friend. The small talk ensued while I finished my first drink and started on the second which went down even smoother than the first. I tend to drink more when I am nervous. Tim was in sales and as we talked, I noticed he used his hands a lot and playfully made fun of it. He told me it was a habit from sales and placed one on the back of my barstool and the other on his thigh which. The conversation continued and Tim moved his hand to my thigh. I smiled and took another sip. His hand laid gently on my thigh right at my dresses hem line. I tried to ignore it, but was slightly turned on by his forwardness. He asked if I wanted another drink and I told him to hold that thought and excused myself to the bathroom.

The bathroom was empty and I went and peed in the stall and texted Jake and got no response. I called and after the second attempt, he picked all groggy and apologized for passing out. I realized that if he came down to the bar it would be just for me and the thrill wouldn’t be there so I told him to stay in the room to which he thanked me and said that he “owed me a big one”. I told him that I was hanging out with some people and would be back in a bit. He said “ok” and hung up with no “love you” or even a “bye”.

When I returned, Tim got up and greeted me and I told him that him that I would have one more before I was going to call it a night and that my friend had cancelled. As we sat back down, I noticed the barstools were a little closer and his hand returned to the back of my stool and his other hand returned to my thigh after he ordered another round. I had a nice buzz going after drinking two cocktails on an empty stomach. Our round came and we cheered and I took a sip of what seemed like rocket fuel. Tim saw my expression and asked if I wanted a new drink. I got the bartenders attention and asked to top it off with more cranberry juice, but before he did, I took a big gulp to make space. That gulp seemed to go right to my head in a matter of seconds. The conversation went back and forth and Tim’s hand slowly moved from the top of my thigh to the inside and stared to disappear under the hem line. I was getting drunk and getting really turned on and my nervousness was almost gone. My breathing picked up, my nipples were getting hard, and I was losing concentration.

Tim’s hand could not go any further without him being forceful. He patiently caressed the inside of my thigh and was telling me about his company. Blah Blah Blah, like the teacher from Charlie Brown. My mind was focused on his hand and my inhibitions were fading. Options were racing through my mind. Just sit there and see if he gives up or forces his hand higher or I give in and see what happens. I adjusted myself forward and slightly spread my legs on the stool giving him the slimmest of access to move further up my thigh. I felt I was teasing him, when in turn he began to tease me. He took advantage of the opening and slid his hand up my thigh and his finger began to graze my slit through my panties. At first touch, my chest tightened and I began to breathe deeper. His finger slowly danced up and down my slit. I was getting really aroused. He wasn’t being forceful which turned me on even more. The conversation continued as a tried my best to keep my composure. I adjusted again, giving him, a little more room and he zeroed in on my clit. I took a drink and smiled as I got lost in the alcohol and his finger. His finger would alternate between doing little circles on my clit and pulsating pressure then slide down and up the length of my wet slit. He was dominating the conversation and me and I was completely lost in the situation. The pace of my breathing picked up and I let out a little moan as his finger did another length of my slit, but this time with a little more pressure. He leaned into me and asked if was alright and I nodded and leaned into him for a kiss. We kissed and his finger pressed deeper into me only being held out by my panties. Our heads separated and he whispered in my ear that he wanted to take me upstairs. I was a minute or two away from having an orgasm on the barstool and I agreed without giving it any thought. He removed his hand and reached into his pocket and place a bill in the bar and took my hand and guided me out of the bar and towards the elevators.

We got to the elevators and waited briefly with another older couple. I became self-conscious and leaned into Tim and he put his arm around me. The doors opened and two other groups joined us in the elevator. Buttons were pushed. Tim took out his room card and slid it in the slot and pushed the top floor button. One of the older women looked at us and I smiled as Tim and I settled in the back of the elevator. His hand drifted from the small of my back to my ass. After the first group got off, his hand was now under my dress on my bare ass. He was in control and I was loving every second of it. Two more stops and the elevator was finally ours for a four floor ride. As soon as the doors closed, he turned into me and kissed me and his hand squeezed my ass. I melted into him as the elevator reached his floor. The doors opened and he grabbed my hand and led me to his room. At this point, I knew there was no turning back and any thoughts of guilt were nonexistent and I was fine with that.

We got into his suite which had a nice sitting area that the bedroom opened up to. The bed looked bigger than mine a few floors below and the mattress was much higher. I excused myself to the bathroom and peed, freshened up and checked, then muted my phone. I was still drunk, but coming down and in more control than I was 15 minutes earlier. When I returned, the lights had been dimmed and Tim was making himself a drink at the bar. He offered and I declined, but then asked for a Coke. I came up behind him and slid my arms around him as he poured my drink. I am 5’8 and with my heels I was matched his 6 foot plus frame. I kissed his neck and then nibbled on his ear. He finished pouring my drink. I whispered in his ear calling him a dirty old man and asked him if he liked getting me off in bar. He smiled and told me, yes. I reached for my drink and downed most of the glass. The sugar and caffeine felt great. He took a sip of his a put down his drink and took my glass and turned and kissed me. I separated before we got carried away and led him into the bedroom where there was a full-length mirror and asked him to help me out of my dress.

He kissed my neck and took his time unzipping my dress. His fingers slowly pushed it off my shoulder and it dropped to the floor. I watch him survey my body in the mirror. He told me that I looked amazing in my dress and for a second, he said he was speechless when he saw me naked. All I had on were my panties and heels. He placed his hands on my hips and continued kissing my neck. I watched as his hands slid up to my breasts and he began squeezing them and working my nipples between his thumbs and fingers. He was a little rough and it turned me on. I leaned back into him and turned my head to kiss. It was sloppy and mostly tongue. His right hand released my breast and I watched it slide over my stomach and disappear in my panties. He grinned and whispered an “oh my god” in my ear as his finger entered my soaked bare pussy for the first time. I had gotten completely waxed for the first time for this trip and the feeling was mind-blowing. He asked if I liked watching and I nodded and kissed him again. I reached behind and began rubbing the bulge in his pants. He picked up the pace in my panties and a felt I was about to cum. I let go of his cock and arched my back into him and moaned. My hips bucked as I covered his hand with my juices. He continued to with hand and I spun around and began kissing him. I was soaked and his continued to rub and tease my pussy as I moaned, breathed heavily, and kissed him.
I rubbed his bulge and began undoing his belt and button on his pants. I looked him in the eyes and told him it was now his turn to watch and he gave me a big grin and I lowered myself down to my knees. I didn’t waste anytime and I pulled his pants down and he stepped out of them leaving only his boxers. I slid my hand and over his cock and outlined it in his boxers and without even seeing it, I knew it was going to be one of the bigger ones of my limited number that I had sucked. I was getting anxious and gave his boxers a tug making sure to give his cock enough space to spring out. I immediately wrapped my hand around it and began giving it gentle strokes. It was one of the longer ones I had experienced, but its girth made it the largest cock that I had ever encountered in my limited experience. I began licking and kissing the head while I stroked it. I made eye contact with Tim as the head disappeared in my mouth for the first time. I then began the slow bob sending it deeper and deeper in my mouth with every stroke. His breathing picked up and he began moaning every time I changed it up. I looked up at him with the head of his cock resting on my flickering tongue. He reached down and grabbed my hand that was pumping his cock and grabbed my other hand that was resting on his hip and held them over my head as I took him deep in my mouth. I picked up the pace and he gave me a “yeah that’s it” and “oh my god”. Part of me wanted to make him cum, but my pussy was overriding any of those thoughts. I slowed the pace down and removed his cock from my mouth and rose up to kiss him. He told me that any longer and would have cum.

Tim led me to the bed and began kissing me. It was brief as he worked his way down to my breasts. I watched as he sucked, nibbled and tugged on them and loved the attention he was giving them. He then leaned into me, nudging me onto the bed with his body weight. His hands slipped up my thighs to my hips and he pulled me to the edge of the bed and began removing my panties. As soon as the were fully removed, I spread my legs and gave him the full view of my waxed pussy. He methodically worked his way kissing down my thigh until he reached my pussy which he greeting it with a flicker of his tongue. I loved every minute of him going down on me. His tongue flickered my clit with intermittent long strokes down the length of my pussy, to sucking up my juices. He used his finger to tease the base of my pussy, never fully entering me. I wanted him to bury his finger in me, but he wouldn’t give me that pleasure. His finger occasionally drifted lower towards my anus and applied pressure, which drove me crazy. I grabbed two handfuls of sheets as my hips were undulating and my moans were getting longer and louder. I came as his tongue lapped up my cum.

He stood up and readjusted me to the edge of the bed and began teasing my pussy with the tip of his cock. I was breathing heavily and moaning with every movement. I finally begged him to fuck me to which he shifted his weight and leaned into me. I was tight and he slowly worked his cock deeper and deeper with every stroke until finally he was able to drive deep inside of me and our hips met. He was gentle and methodic with his strokes. I was seeing stars and my whole body was tingling. I had never been fucked like this and my body was craving more. He pulled out and told me to slide back and he followed onto the bed. I opened my legs inviting him back in me as he positioned himself for more. I was tight and soaking wet and he filled every inch of my pussy. He picked up his rhythm almost immediately and I had lost track of how many times I had cum. His hands worked my breasts and every time he pinched my nipples a current ran though my body. He then slid his hand underneath my ass propping my hips up and began taking long and deep strokes. The angle was amazing. He then worked his hand between my ass cheeks and his finger found my anus. For the most part my anus was off limits, but I was so lost and caught up in moment, I wanted it. His finger applied pressure and teased my anus which heighted my overall pleasure and I went over the edge when his finger entered me. I let out a loud moan and he continued pumping my deep like a piston.

I was loving every moment, but wanted him to cum. I told him “cum for me baby” which has worked on previous guys and he asked if I wanted to ride him. I told him no and to fuck me harder. Tim pulled out and flipped me over like a rag doll. Without hesitation, I propped my hips up for him to enter me. He slid right in and his pace quickened and I lowered my hips to get an amazing angle where every one of his thrust felt awesome. I had never cum in the doggy style position without digit assistance. This time was going to be different. I could feel an orgasm coming and started to talk dirty to him. I told him to “fuck my pussy deeper” to which he drove it hard and deep inside of me. I came almost immediately. I could hear the squishy sounds with every thrust. He then pulled and rested his cock between my ass cheeks and pressed them together and thrusted. He grunted and moaned followed by an “oh my god” and I could feel his hot cum land on my back as high as my shoulder blades. When he finished, he collapsed next to me and began kissing me gently and telling me that it fucking amazing. My pussy was smoldering from getting fucked so good. I had never cum like that and as many times. I had never been fucked remotely close to the way Tim fucked me. Tim got up and got a towel and wiped my back as I was drifting. He then wrapped us in the comforter and I drifted into a post sex slumber.

Source: reddit.com/r/gonewildstories/comments/bn6hh4/role_play_to_reality_fm_long