My First Time As a Sugar Baby [FM]

After two meetings with a “friend” of a girl on my hall, I found myself sitting at a bar with a drink and looking a my watch. It was 3:52 and I was nervous and questioning why I was here. “What was I doing?” ran through my head. I tried to reason with myself that I was bored with college life after only a few weeks. I scanned the room and made eye contact with some men that I thought could be my new “companion” for the evening.

At 4:00, the bartender handed me my credit and pointed me towards a gentleman tucked away and sitting in a booth. I picked up my drink and did my best not to stumble or make an ass of myself as I made my way towards him.

He was tall and fit with salt and pepper hair. He smiled and stood up and greeted me and ushered me in to the booth.

We chatted for a bit and had another drink. My nerves were calming but I still had a knot in my stomach.

He was confident and seemed to know the routine. He told me that we had some time before dinner with a business friend and we could walk around and talk. He paid the tab and we were on our way.

At first, I was walking next to him, and after a block or two, he hooked my arm and I nuzzled closer.

We walked by a few shops and finally stopped at one. I sensed and later would find out that he had a plan. We walked in and he pretended to look around, but spent more time watching me. I was familiar with what I was doing, but not well versed in the protocol. I gravitated to a black dress. It was much nicer than the one I was wearing, and way more expensive. We finally met at the lingerie and he watched me more intently. Finally, he asked what I liked and I told him that I saw one or two that I liked. As the saleswoman turned away to help another customer, I whispered in his ear and asked what he like and wanted to see me in. It was the first time I saw the devilish grin on his face.

We left the store. I was carrying the purchase and had hooked his arm. What I was doing had sunk in and I was trying to feel more comfortable.

He wanted to head to his hotel and drop off the bag, then we were off to dinner. The hotel was a few blocks away and we made it up to his room. It had a nice sitting area and separate bedroom. He took my coat and offered me a drink. There was a slight awkward silence before he cheered me with “to meeting you”, then we both took a drink. I did not know what to do and was waiting for him to make a move, and then he finally did. He stepped closer and leaned in for a kiss. It was confident and soft, yet affirmed that he was in charge. Our heads separated and I lingered relishing in the kiss. He smiled and told me that he was going to take a quick shower before dinner and I was welcome to put wear the purchase.

I watched as he closed the sliding doors to the bedroom and head the shower start. I sat on the couch and opened the box. It was black lacy bra and panty set and I had never worn anything that expensive. I got out of my dress and adjusted the bra and looked at myself in the mirror before slipping my dress back on.

A few minutes later, the shower stopped and he appeared in the doorway in a robe. I saw that his glass was empty and offered to make him another drink. He told me that I had read his mind and then asked if “we” made the right decision and I smiled and said that he’ll have to tell me later on this evening.

As I was pouring his drink, he came up behind me. I had a feeling that he wanted to see the purchase before dinner. He pulled my hair to the side and kissed my neck, then worked up to ear and gave it a nibble. He turned me to face him and we kissed. This time, the kiss was more direct and longer.

Our head separated and he told me if we continue, we will miss dinner and we can’t do that. He reached out and pinched my nipple which caused me to take a deep gasp, and I looked him in the and smiled as he finished.

He then reiterated that we had to stop. I asked him how much time we had, and asked what I had in mind.

It was right then that I began to embrace what I was doing and started to feel confident.

I looked him in the eyes as my hand slid into his robe. The grin reappeared as I gripped his semi-hard cock and gently stroked it while keeping eye contact.

He watched as I lowered to my knees and looked up at him.

“Do we have enough time for this?”

He nodded and grinned wider as he watched my tongue dance on the tip of his hardening cock.

His robe opened as I began working his shaft with my lips. My eyes wandered over his fit early 40’s body before closing as I began working him deeper in my mouth. He was average length and above in girth and I enjoyed how he filled my mouth.

I stroked and bobbed on his cock with intermittent focus on his tip and shaft while making eye contact the whole time.

He muttered a few “oh my god’s” and a “holy fuck yeah” as my lips met the base of his shaft.

I picked up the pace and just focused on pumping and bobbing. He let out a moan and I matched him with one while his cock was in my mouth. I tasted his pre-cum and my lips locked on his frenulum and my pumping of his shaft increased. His knees weakened as his hips bucked and I sucked harder like a vacuum as his cum entered my mouth. I looked up as I pumped out his remaining cum into my mouth.

I kept my eye contact with him as he watched me press his tip into my puckered lips and my tongue swiped the last droplet of his load. I moaned with joyful delight and savored pleasing him.

He helped me up and I reached behind him for my drink. His hand went under my chin and he told me that it was unexpected and amazing, before kissing me.

I bit my lip and smiled before taking a drink.

“You should hurry and and get dressed, so we won’t be late.”

He smiled and made his way into the bedroom, and I headed to the bathroom to freshen up before heading to dinner.

** To Be Continued **

Source: reddit.com/r/gonewildstories/comments/zpwqs4/my_first_time_as_a_sugar_baby_fm