Diary of a Weak Man Ch. 01

March 19,

I haven't written in this journal for a long time, but I had an amazing night, and felt I had to express how excited I am.

Tonight I went out to meet up with Jerry. I was reluctant to go since Jerry is such a player and I always end up watching him smooth talk the girls while I sit alone. I have been feeling pretty down since I broke up with Becky last summer. Anyway, the night started off as usual. Jerry and I chatted a bit about his recent exploits, then he disappeared. While sipping on my beer I saw him at the other side of the bar, reading the palm of a pretty brunette girl. He loves that move, he says it gets him touching the girl and from there he keeps pushing things. It works for him but never has for me.

Things took a major turn for the better when a pretty Asian girl joined them. She looked even prettier than the girl Jerry was chatting up. Soon Jerry waved me over and introduced me as his buddy. The Asian girl's name was Kim, and I was a little tongue-tied when I shook her hand. She had a bright smile, one that you couldn't resist returning. Kim, who from the flush on her face had evidently already had a few drinks, suggested we order a round and I happily bought for the four of us. It had been a long time since I had such a beautiful girl to keep me company. Kim carried the conversation easily, and I felt very comfortable with her. After a couple of drinks, Jerry and the brunette left us. Kim giggled a few minutes later, pointing out that Jerry and her friend were making out in the corner. The drinks had given me false courage and I asked her if it would be ok if I kissed her. Kim giggled again and told me 'sure. Her lips felt amazing when I kissed her. After a few seconds she pulled away and started giggling more.

"You're the second boy I made out with tonight!" she exclaimed.

I laughed, not sure why I found this funny, but her laugh was infectious. I begged her for her number and she gave it to me! I even tried it before she left to make sure it was real. She is so sweet and I really want to see her again. I jacked off as soon as I got home imagining what it would be like to see her naked. I'm still quite buzzed as I write this, both from the drinks, and the excitement of having met such a special girl.

March 25,

After several texts and calls, I was lucky enough to get Kim to pick up. I hadn't been able to get her out of my mind and told her so. She said she remembered me, and apologized for being so drunk that night. Kim explained she had broken up with her boyfriend the day before and was out with her friend to forget about him.

I asked if she would ever go out with me and she said yes! She said she was booked for the next two weeks but could see me on the Friday after next. I got hard just hearing her voice and can't wait for two weeks to go by.

April 6

Jerry invited me to go out tonight with a new girl he has been seeing and her sister. He said her sister was kind of slutty and should be an easy mark. Jerry is worried because he knows I haven't fucked a girl since Becky broke up with me.

We had a pretty good time. The girl was pretty enough, and was dressed quite sexy, but I couldn't stop thinking about Kim. They suggested we go back to Jerry's place for more drinks but I begged off since I had to get up early for work. When I got home I jacked off imagining it had been Kim wearing the short skirt the girl had been wearing.

April 18

I finally got to see Kim tonight. She postponed our date a couple of times, but I was persistent. She was all apologies and giggled that she has been very popular lately. She was very casually dressed in a simple white, sleeveless top and denim shorts. She wore open toed sandals and I admired her pink toenails. Kim is petite but the outfit showed off her smooth skin and perfect legs. She is really a gorgeous girl.

I was a little over-dressed compared to Kim as I wore dress pants and a jacket. I took her to a nice restaurant and she seemed to really enjoy it. Kim charmed the waiter with her smile and easy manner. We got great service and he even bought her a drink!

Kim explained that her old boyfriend, named Mike, never really took her anywhere. When I asked her why she ended up telling me all about him. Apparently Mike is a cop. She fell for him right away when she met him, mainly because of his looks and confidence. She had dated him for six months. She said Mike liked to control her and she was ok with that, but she didn't like how jealous he was. She explained she was naturally flirty but didn't mean anything by it. They would fight about her talking to other men but it was Mike's cheating that broke them up. When she caught him a third time she finally called it off.

I was genuinely shocked anyone would cheat on Kim and told her so. She said I was 'so sweet'. Score for me! Kim explained that her ex., was very good looking and girls would throw themselves at him. She said she really missed Mike, but she knew she was better off without him and was excited to be so free. I empathized and she again told me how sweet I was. After I paid for the bill, I ordered her an uber, and she gave me a kiss on the cheek. I wanted to kiss her again, but I was shy and before I knew it she was in the car. I jacked off as soon as I got home.

April 26

I had been trying to reach Kim for a week and she finally returned my text late last night. She replied back around 11 saying, "Are you around now?" I was worried about being out late before work this morning, but told her I was. She asked me to meet her at the bar down the block from her apartment. I got there as quickly as I could and when I arrived I saw her at the bar. She looked very pretty in a short black dress, but she also looked sad. I asked her what was wrong and she started in on a long explanation of how she had met up with Mike earlier that night. She knew it was a mistake but she wanted 'closure'. She met Mike at his apartment, and she explained that after talking a little she found herself bent over a table while he spanked her then took her. Mike had made her admit that she had been fantasizing about him as he fucked her. Afterwards she felt degraded and disappointed in herself because he refused to tell her he would stop seeing the girl she had caught him with.

I stroked Kim's hand, looked into her big brown eyes and told her it would all be ok. I was turned on by imagining Kim doing all this for Mike, but of course I couldn't tell her so. We talked a while longer and finally she said she should get going. I tried for a kiss on the way out, but it was a little awkward. Kim giggled when she felt my hard-on press against her, kissed me on the cheek again and told me I was really sweet. She said we should see each other soon.

When I got home I jacked off, imagining Kim bending over, being spanked and fucked. She looked so innocent and seemed so nice, it made it even more exciting to imagine this. I came quickly and fell asleep with tissues in my hand.

April 30

Kim replied to me sooner now. I feel like we have a real connection. She said she really enjoyed talking and remarked what a good listener I am. I asked her to see me Friday and she agreed to Sunday. I can't stop jacking off imagining her.

May 5

I got to see Kim tonight! I took her to a very nice place because she wanted to go and I knew she was feeling down. I was a little shocked at the prices when we arrived, but she seemed to really appreciate it. She wore a blue dress, more conservative than the one she had worn at the bar last time, but she still looked so sexy. We sat side by side and got a nice bottle of wine, then another and we both got tipsy. Kim's face was flushed red. I couldn't stop staring at her body as she told me about her classes. She wanted to get dessert and as we shared it she surprised me by saying,

"You've been staring at my legs all night. You can touch them if you want."

My heart beat fast, but I didn't hesitate long. I reached over and stroked her bare leg. She felt so smooth I wondered if she every had hair on her legs. Kim giggled and pointed at my erection. I blushed. I was so used to being hard with her, even thinking about her, I hadn't even thought about it.

After dinner, we lingered on the street outside the restaurant. Kim, who had had a bottle of wine to herself over the evening, pushed her body against mine and kissed my lips. I pushed my erection against her rather desperately and she giggled and pulled away. I told her I had been fantasizing about her and she giggled again then squeezed my cock through my dress pants.

"Sweet dreams tonight." she said teasingly.

I got one more kiss on the lips before I hailed a taxi for her. I thanked her for coming out and made her promise to see me again soon. Of course when I got hope I jacked off furiously.

May 11

After not hearing from her for a few days, despite many texts, Kim surprised me by texting me a little while ago. It was already rather late, but she asked if I was around and said she wanted to come over. Of course I was very excited and cleaned up my place as she was on her way. When she arrived I was taken aback by how sexy she looked. She wore a tight red top that was shear enough to show off a hint of nipple, and short white skirt. She kissed me in the cheek as she brushed by me into my place. It became evident that Kim had had a few drinks. She was flushed and talking fast, asking for wine, which I got her.

She explained that she had been on a date with a guy she met on Tinder. Kim flopped on my couch, lying down on her back and sighed. I sat beside her and tentatively started to rub her feet while she told me about her evening. I used to rub Becky's feet regularly so I am pretty good at it. I was glad when Kim did not object. I was very hard by touching her and looking up her skirt but tried to be discrete.

Kim told me the guy was 'really cute'. I felt a little bad having her tell me about another guy while she was visiting but I was excited to be so close to her and didn't want to spoil it. I continued to rub her soles.

She said she was attracted to him, and that after drinks he took her by the hand, took her outside the bar, then pinned her against a wall. He kissed her hard, pulling her hair, which she said she loves. She said she was like putty in his hands, but when she whimpered that they should go somewhere he suggested her place. Kim had a hunch and asked if he was married and he admitted he is. She said she was tempted to fuck him anyway, but she knew that would be another bad decision.

Kim continued, slurring her words a little, "It's just that sex with Mike was amazing, you know? God, I loved it when he spanked me."

Kim took a breath, apparently indulging in a memory. She then paused, looked at me with a little smile, then took the foot I was not massaging and rubbed it along my lap. Her toes squeezed my hard cock.

"Mmmm...you like it when I talk about Mike don't you? You like to imagine me with him?"

I didn't know what to say. I couldn't help imagining her with Mike when she talked about him, but of course I would prefer she was focused on me. All I could think of is that I didn't want her foot to stop stroking my cock. I felt my face go red.

"Maybe we could do a role play?" she cooed teasingly, "Would you like to play being Mike?"

I found myself nodding without even thinking. I don't think I could ever say no to Kim.

Kim took her foot away, got up from the couch, and looked down at me while giving me instructions for the role play. She reminded me that Mike was very aggressive. Suddenly she switched into the role play.

"Hey Mike...it's good to see you again." she said almost shyly. "I've been thinking about you."

I tried to summon my inner alpha and spoke a little gruffly, "Hey, thanks for coming over."

Kim grimaced and I realized that Mike probably wouldn't have thanked her. I tried to reassert myself as Mike.

"Last time I saw you, you were bent over the table...ummm...why don't you position yourself like that again?"

Kim giggled and said, "You've been thinking about that have you?"

I wasn't sure if she was talking to me or 'Mike', but I watched my dream girl bend over my table and ask "Should I lift my skirt?"

I nodded, my throat feeling dry. I watched as Kim playfully took her time in raising her skirt inch by inch, revealing more and more of her legs, then the curved whiteness of her ass cheeks under her thong. Finally her ass was fully exposed except a thin strip of black fabric that ran along her ass crack. I swallowed hard, thinking of how many times I had fantasized about Kim looking like this then realized she was looking at me expectantly.

"I...think it's time you were spanked." I said trying to make it sound like a demand but also making sure she was comfortable with all this.

Kim said nothing, simply wiggling her ass a little. I walked up to her, my heart beating fast.

I had never really spanked a girl, but was excited by the idea of touching Kim's beautiful ass. I reached back and swatted her left ass cheek, not too hard but hard enough to startle me with the noise. Kim groaned, seemingly appreciatively, but I was careful to go a little softer with the next spank. I swatted her three more times, knowing I was not playing Mike that well but unable to will myself to spank her the way she seemed to want. I started to stroke her ass, which was a little pink. God her skin felt amazing.

"You took it easy on me." Kim said looking over her shoulder. "Maybe you just want me to ride you?"

I was a little startled by the suggestion, but I certainly loved the idea. I nodded in agreement and Kim got up. I watcher her drop her skirt to the ground and remove her panties. I started to unzip myself, but Kim took me by the hand and led me to my bedroom where she pushed me on the bed. I was so excited I felt sweat forming on my forehead. Kim climbed on to the bed beside me then unexpectedly straddled by face. Her shaved pussy was now pushed into me, and I licked her gratefully. Becky had taught me the way she liked to be eaten and I was determined to give Kim the best I knew. Kim seemed to have other ideas though, telling me in a deeper voice than normal,

"Oh Mike, I have missed riding your hard cock. Fill me up!"

Taking her cue I tried to make my tongue stiff and long. Kim started to ride my face, moving her slit up and down my tongue. I tried to take little breaths from my nose when she would allow me the chance, all while keeping my tongue still for her.

"Ohhh...make me your slut Mike. You know I want to be your good little slut!"

Her words struck me as harsh, but I did not think of it long, as I was so focused on making sure she could continue enjoying my tongue. She did this for quite a long time, sometimes encouraging 'Mike' but largely just moaning. She was very wet and I felt her dripping on to my cheeks. Kim started riding my face faster, until her breath quickened and she became louder until finally I could feel her tense and go quiet.

I felt proud and was thinking I would now get to fuck her, as Becky would let me do after I made sure she came. When I pulled out my cock Kim encouraged me,

"That's right Timmy...you stroke it for me."

I was a little confused by switching away from the role play...and nobody called me 'Timmy', but I grabbed my twitching cock. I thought I would stroke it a little for her then she would possibly suck it for me, but as soon as I stroked twice, looking up at Kim's beautiful face smirking down at me, I knew I could not hold back. I came very quickly into my hand. Kim climbed off and went to my bathroom with her skirt. Before I was done wiping myself off on my sheets Kim was back out. She smiled as she kissed me on the forehead, telling me she had fun.

"I promise I'll see you soon sweetie." she said then I watched her turn and leave my apartment. That was just 10 minutes ago now...I am lying here in the bed, still warm and wet from all the fun we had.

I have to text her and tell her I can't wait to see her again.