On our way to dinner and he explained the situation. We were having dinner with a business associate of his, and he was also going to have a “friend” with him. She was older and had known the business associate for only a few minutes before we arrived and their “relationship” was not planned to go beyond the evening. Ohhh, what you can find out in the ladies room.
Dinner went as well as I could have expected. As the two men talked, us ladies did our best to make small talk and try to participate in their conversation from time to time. There was no lingering afterwards and we headed back to the hotel. He wanted to make a stop in the bar for a nightcap. I had paced throughout dinner myself and agreed.
As we had our drink, he complimented me on my dress and how I carried myself at dinner. His hand rested on my thigh, and inched ever so slightly higher as the conversation veered in my comfort level with what was about to when we got to his room. I spread my legs ever so slightly, to give him a little more access as I assured him that even though it was my first time, I was completely comfortable with what was going to happen. His hand came just short of making contact with my panties. If he went any further, it most likely would have looked awkward by anyone that glanced our way.
We made our way back to his room. I excused myself to the bathroom and peed, freshened up and checked, then muted my phone. I had a giddy buzz, but was incomplete control. When I returned, the lights had been dimmed and he 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 a match for 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 if he wanted 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 shoulders and it dropped to the floor. I watched 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 in what had been purchased earlier. He placed his hands on my hips and continued kissing my neck. I watched as his hands slide up to my bra and he began squeezing my breasts and working my nipples between his thumbs and fingers through the lace of the bra. His hand disappeared and my bra snapped opened and I watched it drop to the ground and his hands replace it. 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. He tugged at my bare nipples and squeezed my flesh which made me give off a moan. 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 and the feeling was mind-blowing. He asked if I liked watching and I nodded and kissed him again. I reached behind myself and began rubbing the bulge in his pants. He picked up the pace in my panties. I was completely turned on in a way that I have never been. His finger zeroed in on my clit and I spread my legs a little more. My moaning increased only to be muffled by a periodic sloppy kiss. I let go of his cock and arched my back into him and moaned. My hips bucked and my knees gave out as I covered his hand with my juices.
He continued with his hand in my panties and I spun around and began kissing him. I was soaked and his continued to rub and tease my pussy as I moaned and breathed heavily. 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 kissed it through his boxers before giving them a tug.
I immediately wrapped my hand around it and began giving it gentle strokes. I began licking and kissing the head while I stroked it. I made eye contact with him as the head disappeared in my mouth and his devilish grin was in full force.
I slowly worked him 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”. 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.
He led me to the bed and began kissing me. With a gentle push, I found myself on my back on the bed. He climbed on top of me and we kissed briefly before he worked his was lower to my breasts. I watched as he sucked, nibbled and tugged on them and loved the attention he was giving them. He slid off of the bed and his hands moved 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 freshly 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 methodical 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 heightened 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.
My head was spinning and my body was overloaded with pleasure. I was in a sexual place that I had never been before. I wanted him to cum, and muttered “cum for me baby” which has worked on previous guys. He asked if I wanted to ride him and I told him no and to fuck me harder and deeper. He 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 of my pussy with every thrust. He pulled and rested his cock between my ass cheeks and pressed them together and thrusted. I heard a grunt and moaned followed by a stuttered “uhuhohhhhhh” 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 he fucked me.
He got up and made his way to the bathroom to get a towel and came back and wiped my back as I was drifting in a post orgasmic haze. He pulled the comforter down and I slid my used body under it and nuzzled up next to him. We kissed a few more times for drifting into post coital sleep.
** To Be Continued **
Source: reddit.com/r/gonewildstories/comments/zqzmmt/my_first_time_as_a_sugar_baby_part_two_fm
Absolutely loved it. Looking forward to reading more