My First Blow Job

Online dating is challenging. You just never quite know what you are going to end up doing when you meet.

I met Charles for a first date on Wednesday evening, in between my day job and night job. I was clear that if that was when we were to meet that I would only have an hour, but if he wanted to have a longer date, then we could meet for a late supper after 11 pm when I got off work. He chose to stick with the earlier time, but suggested that if we really hit it off, maybe we could meet up again for that late dinner or perhaps drinks.

We met in a pretty little parkette near a gazebo in a trendy section of town. We walked, talked, stopped into a cool little bistro and before we knew it, our time was up and I had to leave for work. He walked me up the block, to a halfway point between where our cars were parked. I expected a kiss, the vibe was definitely there, but then he just shook my hand. As I was about to leave, he gave me a very intense look and held my hand for a long moment, but nothing else, so I decided to move on as I could not fathom what he was thinking or feeling and I didn't have the time to spend figuring it out.

I got to work and quickly texted a thank you for the drink and snack we had and wished him well, being polite and giving him an easy out to just walk away as I took the lack of a kiss as lack of interest. My work place is a secure facility with confidentiality issues, so no cell phones are allowed on the production floor, therefore my phone went into my bag for the next three hours. When I got off work, just after 11 pm, I had 3 texts waiting - one to say he enjoyed meeting me and asking if I would join him for drinks later, one to ask if I would be comfortable meeting at his hotel bar for said drinks, and one asking if I was "pissed" at him.

I texted back to say I had just gotten off work and received his texts. I laughed and asked why should I be pissed, had he done something bad that I had missed?

He texted back to say he thought maybe I was upset that he would invite me to a hotel on a first date.

I pointed out that it would technically be a second date, and no, I wasn't pissed as we had already discussed potentially meeting up later and due to the time of night, a hotel bar made sense since most other places would be starting to close down.

After some banter we decided to meet for drinks. I quickly changed my clothes and headed off for his hotel, excited to see if we would continue to hit it off as we had earlier. He texted me while I was en route to ask if I really was coming, as if I was, he would have to get dressed as he was stark naked in bed.

This text was a departure from all of our previous texts and conversations. In a lighthearted but clear way, I stated that drink did not mean automatic sex pass, so he better get some clothes on. He graciously said "too bad" and that he would get ready right away.

By this time I was almost to his hotel and upon arriving, texted to ask where to meet, in the lobby or bar. He said he was just finishing getting ready, so if I wanted, I could just pop up to his room and we could go to the bar together. This seemed sensible since walking into a hotel bar alone at midnight definitely puts out the "woman on the prowl" message.

I jokingly asked if I could trust that he wouldn't be opening the door naked. He said what did I think he was, some kind of perverted prick? I said, I never said you were a prick.....lol.

I arrived to his room and he called to find out when the bar closed. We would have half an hour if we went down right away. He said he didn't really feel like drinking alcohol and said if I didn't as well that we could just relax, talk, get to know each other better. Apparently I am very naive, as I thought that was a nice suggestion and we might even end up sharing that kiss I had been expecting earlier. He told me later that he had every intention of fucking me when he had suggested we should stay in the room.

I curled up in the desk chair, carefully choosing not to sit on one of the two big beds in the room. He sat on the bed and we made small talk about what he had been watching on tv (politics). He turned off the tv and suggested I sit near him - of course on the bed - so that at least we could look into each other's eyes as we talked and maybe cuddle. Yes the red flags went up in my head at that, but I also am working on relaxing my outlook on anything to do with sex and relationships, so I agreed to sit with him on the bed to cuddle and talk.

As soon as I was settled, glasses off, propped up on pillows, he gave me the same intense look he had given me earlier. I found the silence unnerving so I asked him a question about why he chose his profession. He looked a little surprised by the serious question, but he relaxed and started talking about his life for about 40 minutes then we talked about mine for another 15 or so.

He then adjusted the temperature in the room saying he was cold, then too hot, definitely making a show of fidgeting around. In between temperature adjustments he was giving me very intense looks as we talked and I of course was pretending not to notice them. I figured a kiss was on the way at any moment - I was hoping it would be the defining moment of whether or not I could see us going forward together.

He quite suddenly stood up and said he was tired and wanted to go to bed. I immediately sat up to leave and he asked me to please stay and cuddle as we were getting along so well. He asked me what time I had to get up for work in the morning in case we fell asleep and set his phone alarm. I figured I would stay for a little bit and see how I felt about things. As soon as I lay back down to get comfortable, he pulled his shirt over his head. I was not surprised as I know most men do not like to feel constrained by a shirt when they are in bed. Besides, I enjoy touching a man's chest if we are cuddling, so I was onboard with that. He then mentioned that as he said earlier, he sleeps naked and before I cold bat an eye, his pants were around his ankles. I looked away and tried to decide what I should do and in the meantime he quickly hopped into bed under the covers and settled back against the headboard.

I was on top of the covers so I felt that I was still in charge of leaving should I wish to. But strangely, I didn't really want to, even though I could see where this might be headed. He put his arm across my pillow, pulling me towards him so that my head was cradled at his shoulder and my hand was splayed across his chest. He was rubbing my arm, encouraging me to explore his chest, and I expected a kiss at any moment.

He stopped my hand, placing his on top of mine and began pushing it down over his stomach towards the edge of the sheet. In a very sexy voice he told me to touch him, stroke him, put my hands on his cock. I tentatively did, sliding my skin over his, feeling the head, the shaft, petting him, circling my fingers around him, telling him I had not played with a man this way since college. He pushed his fingers into my hair and growled at me to "kiss it" and he added pressure to my skull to guide me in that direction. I rebelled, saying that I hadn't even kissed his lips yet, let alone his cock. He pulled my head to his mouth, kissing me, massaging my neck, licking my lips. I responded, sucking on his bottom lip, nibbling, kissing.

After a few minutes, during which time he made sure my hand had not left his groin, we stopped kissing and he strongly pushed my head down towards his waist. I hesitated a bit, fighting my instincts to say no. I took the head of his cock in my mouth, just popping it in then out. I moved my head sideways, running my lips along the side of the shaft, getting it wet, feeling the curves and bulges in it.

He ran his hands back into my hair, pulling it out of the way so he could see, but not letting it go. As I began sucking and licking more of him, he alternately massaged my head and gripped my hair in a very possessive and aggressive way. He pulled my hair tightly in his hand and told me to get between his legs so he could watch better as I sucked him. I told him that I had never given a blow job before, as my previous boyfriend had preferred to get straight into intercourse. He gave a smile and told me again to get between his legs. I followed his instruction and slid further down the bed as he swung his leg over me, trapping me between his thighs.

I began to get more comfortable with his cock, licking it all over, sucking, probing with my tongue, spitting on my hand then rubbing it all over his shaft, getting it nice and wet. He demanded that I suck on his balls so I did, sliding then into my mouth, lapping at them with my tongue. He raised his legs encouraging me to fully take them into my sucking mouth. I continued to alternate between his balls and cock, getting more and more exuberant as he responded to my mouth. I began popping the head in and out of my mouth, the sound driving him wild. I took his cock and ran it across my cheeks, my eyes, all over my face and neck, it's silky skin sizzling against mine. His moans and his enjoyment were making me feel powerful and I was loving having this affect on an obviously experienced man.

I asked if he was getting close as he was very hard and his balls were tight up against his cock. He said he had been holding back because it was so good he didn't want it to stop. My mouth was getting a bit tired and sore so I rolled to the side, continuing to play with his cock as I took a drink of water from a bottle beside the bed. He reached into my shirt, pulling the neckline down, forcing my breast out of my bra cup and pinching the nipple hard. I arched up, reacting to the pain, followed by such a surge of pleasure. He demanded that I take off my shirt and before I could even pull it over my head he had my bra undone and had started molesting both breasts quite savagely. His fervor was exciting me and I relaxed and accepted his attentions willingly.

He pushed me back down onto the bed, pinching and kneading my breasts, telling me how he loved feeling my big tits. He locked his mouth onto my left breast, sucking the nipple, then taking more and more of it in his mouth. He began biting and sucking, so aggressive and dominant. I had my head thrown back, enjoying the feelings coursing through me, my pussy reacting to every tug and lick.

Suddenly he was not touching my breasts any more. He swung his leg over me, straddling my chest in the blink of an eye, pushing his hard cock into my mouth, making me suck him fully. I could barely open wide enough to take his entire cock into my mouth. He was pushing my shoulders down, running his cockhead through my lips repeatedly, loving the sound of me slurping him trying to keep up. As he started to go faster and faster, I tilted my head back, giving him a better angle as he started fully fucking my mouth. He plunged his entire 7 inch cock into my mouth and down into my throat over and over. I gagged on him, but he didn't stop. I ran my nails down the outsides of his thighs and he grabbed my head, holding me still and he pounded my face. I could barely breathe when he grabbed the front of my hair and began cumming deep in my mouth and throat.

My entire mouth filled with cum, warmness running everywhere in my throat, creating a gag reflex and I had to turn my head away to not drown, letting it run from my mouth into my hand. I took his cock in my other hand as he tried to shove it back into my mouth and I began milking him, the cum running into my hair to match the cum dripping down my cheeks and chin. After several minutes of his shuddering climax, he slid backwards a bit so he was over my stomach and my breasts were exposed to him. He again pulled on the nipples, pinching hard as he told me how much fun we were going to have together before climbing off me and going to the bathroom to clean up.

I also cleaned up and although I stayed the night, I never let him take my pants off or play with my pussy although he did ask and try to convince me to go further. I knew that if we started, there was no way I would be able to stop him and I wanted to just enjoy what we had already done. It was fun and exciting and most likely to be continued this weekend as he plans to visit again. He has been texting and calling all week to say what a fabulous time he had and that he can't believe that I hadn't given head before as he thinks that was the best oral sex he has ever received. Maybe a line, but then again, maybe I really am just that good.