It started about 4 months ago. I work installing communication systems in town and had moved to a new area to start a new installation cycle. I found a place in the suburbs with only a short shuttle into the office. I also discovered that there was a “small hole in the wall” called Joe’s Restaurant, about a 5-minute drive from where I was staying.
I like these kinds of places when you get to know the “regulars” and can get comfortable really quickly because of it. My first night there, I met Will, the bartender and a few other folks who are often there. Will was a nice older guy, and the other people were fun to talk to. I asked Will for some food, and he said the burgers there were amazing. When the burger arrived, I took a bite and decided then and there that I would be back again and again.
This bar owner was drop-dead gorgeous
I left later in the evening and knew this would become a regular hangout. I went back a few nights later on Friday night. Furthermore, I noticed that Will wasn’t there, but in his place was the most attractive redheaded lady (trans lady from photo above) I had ever looked at. Besides, I have a weakness for red heads, and this one was drop-dead gorgeous, with the most piercing green eyes to boot.
She was about 5’10” with a round and sexy ass and breasts that men killed to fondle. I was struck. I ordered a drink and finally got to talk to her.
She had a very sexy, husky voice that caused my dick to rise in my pants. I found out her name was Jo and as it turned out, she was not only the bartender, but she was also the bar owner. I commented that she didn’t look like a Joe. She laughed the most amazing laugh and told me her father; the original Joe and bar owner, opened the place about 30 years ago. She bought it from him and just left the name as it was.
No sense screwing with something that works. I agreed and said, “if it doesn’t break, don’t fix it”. She laughed again and said he was the one thinking exactly. Over the next few weeks I went to Joe a couple of times a week. Sometimes I came in for dinner, sometimes just for a drink.
Mostly just to see Jo and bask in her beauty. I was completely captivated. I asked a few regulars if she had a boyfriend or girlfriend, and they all said they’d never seen her with anyone.
My spirits raised. I started talking to her more often
My spirits raised. I started talking to her more often. Although she was talkative, I quickly realized that I wasn’t getting anywhere with her. I would flirt with her, she would flirt back and then go to another customer and do the same. I was frustrated at not getting anywhere with her, but it was tempered in the knowledge that neither was anyone else.
About 3 months into the one way love affair, I observed her at the other end of the bar talking to a drunk suit. I could tell she wasn’t happy with the well-dressed jerk and sent him on his way. When she finally worked her way back to my end of the bar, I asked her about him, and she simply said, “Don’t worry, it’s not your concern,” and went back about her business. I continued unsuccessfully to pursue Jo over the next few weeks, though she seemed to be a bit kinder to me. I continued to flirt and occasionally made creepy suggestions only to be welcomed with a laugh, a smile and a brick wall.
About 3 weeks later, a guy left with a clipboard and some kind of paperwork. He had a very animated conversation with Jo, after which she signed something. After he walked out, she seemed to be visibly shaken. When she came down to me, she told me again: “Don’t worry.” She had it all under control. But I could tell it wasn’t true and that something was really bothering her as she seemed to be on the verge of tears.
That night around 11:00 she announced last call. There weren’t many people there, but they were moaning and groaning about being thrown out early. This had never happened before in all the times I had been there. Nevertheless, she stuck to the last call. I offered to go Jo home, but she politely told me that it wasn’t necessary and that she would be fine.
She pushed me out the door and told me to go home and enjoy the rest of my night. I went thinking that I wouldn’t be able to enjoy the rest of the night without her, but never told her. As I walked outside, it started to rain. I decided to try it again with Jo and went to my car and grabbed an umbrella from the trunk.
I waited outside the bar until Jo finally came out. She saw the rain and I heard her mutter, “Shit! Aren’t those just capes for a fucked up night”. I walked up to her with the umbrella open and said: “Can I help you get dry wherever you go?” She looked at me and I could see incredible sadness in her eyes.
She said: “Thanks for the offer, but I don’t think so. I’m not going to be very sociable at the moment. It would be better for you to leave me alone and go elsewhere.” I looked back into her eyes and told her, “Look, Jo, something is obviously bothering you a lot. You look like you’re about to go to pieces. I don’t know if there’s anything I can do to help, but I’m a good listener and have a pretty comfortable shoulder to cry on if you need it.
But whatever is bothering you, you need to remove it from your sexy chest before you explode. There’s a coffee shop around the corner. Come with me and we can talk.” She smiled at the sexy boob comment and reluctantly agreed to come with me and talk.
We got to the coffee shop and sat down. After the waitress brought us our coffee, I looked at her and asked: “So what’s up, Jo? I saw the guy come in, and you signed something, and then you almost fell apart. Does this have anything to do with the suit that came in a few weeks ago? “” You’re very observant,” she said. She went on to explain that the suit was a lawyer from the bank.
She needed more money to fix something
When her father sold her the bar, he also sold her about $15,000 in loans to the bank. She needed more money to fix something in the bar before she reopened it, and she was now around $ in debt. Business was not very good. She managed to keep the bills paid, but little else.
So now the bank threatened to foreclose on her. The guy who came in tonight was a process server who served her with the papers for the trial at the bank. She looked at me with tears and said: “I don’t know what to do.
The bar is all I have. If I lose it, I’ll be out on the street in a matter of days”. I reached across the table and grabbed her hands.” Well, I’d like to help you if you’ll let me.
I managed to hide a good chunk of change away for the proverbial rainy day. I think this is the rainy day I’ve been waiting for. I’d like to take care of your $ debt, and I’d also like to invest another $ to help repair and do a renovation in the bar. “She looked at me with those beautiful green eyes and asked me,” Why on earth would you want to do this for me? ‘ I looked at her and hummed.” Three reasons.
First, I like your place. It’s the nicest place I’ve ever been, and there’s no way it’s closing. Second, I’ve always wanted to own a bar, to be a bar owner. Mostly I could drink for free, but also because a well-run bar is a good investment. Third and most importantly, I am hopelessly in love with you and I would do anything to help you and bring that beautiful smile back to your face.
“When I spoke to her, I looked directly into her eyes. When I hit the third reason, I saw not only a look of pure surprise, but also just a faint glimmer that told me that there was possibly something mutual there. She looked and me and said: “You’re serious, aren’t you?” I told her absolutely yes on all points.
She asked me what the catch was
She asked me what the catch was. I told her no catch other than she wanted me for a partner and bar owner. The bar was still hers to run as she liked.
She just wanted to see me a little more often, and I got behind the bar privileges. But now she didn’t have to worry about the debt putting her out of business. She thought about it for a few seconds and then said, “In my life, I don’t know why you want to do this, but I will gladly and gratefully accept your offer.” I took her hand, brought them to my face and kissed them. She beamed from ear to ear. I looked at her and said: “That beautiful smile makes the investment worthwhile.” We sat in the room in a happy moment of silence.
After a few minutes, I asked her if I could go with her, and she was happy to. When we stepped out, we discovered that the rain had stopped. As we walked, I took her hand in mine and eventually put my arm around her. She slipped right in, just as she was allowed to go into the crook of my arm. When we got to her door, I leaned over and gave her a light kiss on the lips.
She answered me tightly and kissed me hard, sliding her tongue through my lips. She asked me if I wanted to come in for a nightcap. I said sure and followed her in. Once inside, she turned, put her arms around my neck and kissed me again. This time we exchanged tongues and I took her in my arms and pulled her close.
My cock was about to break out of my jeans when my hand traveled down her back and began kneading her incredibly sexy ass. I pulled her close to me as we kissed, and she moaned as I did. My hands moved up to her breasts and I began to caress the real one. It felt so good in my hand.
I pulled her close again and kissed her on those soft supple lips. I told her through the kiss that I had wanted her from the moment I saw her and that this was a dream come true. I felt her suddenly tense up and she pulled away from me. “Kurt,” she said.
“I’m afraid I’m not the woman you think I am. I think you’re incredibly attractive and sexy, and I want you with every fiber of my being, but I can’t take you any further without telling you the truth.” I looked at her with a very intrigued look on my face. “What are you talking about?” I asked her. She looked at me with those incredible green eyes and took my hand.
She slid my hand down between her legs. Instead of the warm wet pussy that I expected to find, I felt a bump similar to what I felt between my legs. I was confused for a second until I finally realized that what I felt was a hard cock.
The incredibly sexy, loving woman was actually a guy
Yes, this incredibly sexy, loving, caring woman was actually a guy. I looked into her incredibly sexy green eyes and started to say something. I couldn’t think of the right words to say. Jo looked at me and said: “If you want to leave, I understand,” as she looked down at the floor.
I thought for about half a second and realized that I really was turned on by this woman and I didn’t care what was between her legs. I tilted her head back and kissed her softly on the lips. “Yes, I fell in love with you the moment I saw you. Nothing will change that.
I’ll leave if you want me to, but I’ll tell you from this side that I have no intention of going anywhere. ‘ I pulled her close and kissed her hard on the lips. I moved down to her neck and started sneezing and sipping on her neck. I looked up and saw the look on her face and it was truly unadulterated joy.
She took me by the hand, and we walked to her bedroom. “Are you sure about this?” she asked me. I looked at her, smiled and said, “Shut up and kiss me.” When we reached her bedroom, she backed me up to the bed and gave me a little push that made me fall back on the bed.
She pulled the zipper down and fished my cock out of my pants and took it in her hand and began kissing it, stroking it ever so gently. I leaned back on the bed and moaned as her hand and her lips felt so good. She bent her head down and started swirling her tongue around the head of my cock. This caused me to shiver and shake, which she took as a sign to continue. She licked up and down my shaft and eventually took it all in her mouth.
She sucked me like there was no tomorrow and within minutes; I was shuddering and shooting my load of hit cum into her eager hot waiting mouth. She continued sucking until I was dry and clean, and she stood up between my legs. I smiled at her and reached over and removed her jeans, dropping them on the floor. I helped her get out of them. My face was just at crotch level and I could see the bulge in her panties.
It was about 6 inches long and circumcised
I grabbed the waistband on each side and pushed them down to free her. It was about 6 inches long, circumcised and not as thick as mine. I stared at it briefly and then bent my head over and licked the head.
Jo moaned and I reached out and grabbed it. I had never held or touched a man’s cock, except my own, but somehow it just felt so right. She was completely hairless around his cock and balls.
Her cock, though hard, felt soft and wonderful in my hand. I licked the head and began stroking it ever so gently. Jo moaned, and I began to swish my tongue over her head as I had felt her doing against me. Jo grabbed my head and started pushing her hips and fucking my mouth. I tightened my grip on her beautiful cock and began sucking on the head with all the gusto I could muster.
Hearing her moan and feeling her cock pull in my hand and mouth made me light headed and I knew I wanted her to cum in my mouth. I sucked hard and felt her balls begin to tighten. I stroked faster as I sucked hard, and suddenly she let out a moan.
“Ohhhh… baby… I’m going to come!” I locked my mouth over her cock and sucked even harder. I was rewarded with a nice hot load if I came. Not only that, but I sucked it all down and found the taste not at all repulsive. Frankly, I loved the taste. It was sweet and salty and I knew I wanted much and much more.
I took her in my arms and kissed her on the lips
I sucked her until she stopped coming and pushed my head away. We finally undressed and crawled onto the bed. I took her in my arms and kissed her on the lips while stroking her hips. She had my cock in her hand and was looking me straight in the eyes.
“Are you sure you still want to stay?” she asked me. I hummed at her, grabbed her cock and kissed her on the lips. “Yes, I’m not going anywhere until you ask me to leave.
And even then, I might not go. I told you I fell in love with you when I met you, and I wasn’t kidding. “She smiled at me and looked at me with those beautiful green eyes and said. You can stay as long as you want. I’ve wanted this since I first saw you, too, but I was afraid of what you might do when you found out about my little surprise. “She turned around so we could happen.
My cock began to harden again, so I slid it into the crack of her ass and put my arms around her, gently caressing her breast. I smiled and said: “Let’s just say it makes things more interesting, but doesn’t change my feeling for you.” She smiled, and we cuddled up in bed and fell asleep in each other’s arms. The best night of my life was about to get better and hopefully last for a long, long time…