It started about 4 months ago. I work installing communications systems in towns and had been moved to a new area to start a new installation cycle. I found a place in the suburbs with a short commute in to the office. I also discovered that there was a little hole in the wall type joint called Joe’s Bar & Grill about 5 minutes drive from where I lived. I like those kinds of places as you get to know the “regulars” and can get comfortable really quick because of it.
My first night there, I met Tommy, the bartender and a couple other folks who are there frequently. Tommy was a nice older guy and the other folks were fun to talk to. I asked Tommy about some food and he said the burgers there were awesome. When the burger arrived, I took a bite and decided then and there that I would be back again and again. I left later that evening and knew this would become a regular hangout.
I went back a couple nights later on Friday evening. I discovered that Tommy wasn’t there but in his place was the most attractive red haired lady I had ever laid eyes on. 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 would kill to caress. I was smitten. I ordered a drink and finally got to talk to her. She had a very sexy, husky voice that caused my cock 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 owner. I commented that she didn’t look like a Joe. She laughed the most amazing laugh and told me her dad; the original Joe has 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 ain’t broke, don’t fix it”. She laughed again and said that was he thought exactly.
Over the next several weeks I went to Joe’s a couple of times a week. Sometimes I came in for dinner, sometimes only for a drink. Mostly just to see Jo and bask in her beauty. I was totally captivated. I asked a couple of the regulars if she had a boyfriend or girlfriend and they all said they had never seen her with anyone. My spirits soared. I started to talk with her more frequently. Though she was talkative, I quickly realized I was getting no where with her. I would flirt with her, she would flirt back and then go to another customer and do the same thing. I got frustrated at getting no where with her but that was tempered in the knowledge that neither was anyone else.
About 3 months into the one sided love affair I observed her at the other end of the bar talking with some stuffed 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 none of your concern,” and went back about her business.
I continued to unsuccessfully pursue Jo over the next few weeks, although she did seem to be a bit friendlier to me. I continued to flirt and make the occasional lewd suggestion only to be met with a chuckle, a smile and a brick wall.
About 3 weeks later, a guy walked with a clipboard and some kind of paperwork. He had a very animated conversation with Jo after which she signed something. After he left, she appeared to be visibly shaken. When she got down to me she again told me, “Don’t worry.” She had it all under control. But I could tell that wasn’t true and that something was truly worrying her as she seemed to be on the edge of tears.
That night, at about 11:00 she announced last call. There weren’t many people there but they all moaned and groaned about being kicked out early. This had never happened before in all the times I had been there. None the less, she was adamant about last call. I offered to walk Jo home, but she politely told me that wasn’t necessary and that she would be fine. She shoo’d me out the door and told me to go home and enjoy the rest of my night.
I left thinking I wouldn’t be able to enjoy the rest of the night with out her but never told her that.
As I walked outside it was beginning to rain. I decided to give it one more try with Jo and walked over 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! Isn’t this just the capper to a fucked up evening”.
I walked over to her with the umbrella open and said, “Can I help you stay dry where ever you are going?”
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 am not going to be much company at the moment. You’d be better off leaving me alone and going elsewhere.”
I looked her back in the eyes and told her, “Look Jo, something is obviously bothering you a lot. You look like you are about to completely break down. I don’t know if there is anything I can do to help, but I am a great listener and have a pretty comfortable shoulder to cry on if you need it. But whatever is bothering you, you need to get it off 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 chest 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 going on Jo? I saw the guy come in and you sign something and then you almost fell to pieces. Does this have anything to do with the suit that came in a couple of weeks ago?”
“You’re very perceptive,” she said. She proceeded to explain that the suit was a lawyer from the bank. When her dad sold her the bar, he also sold her about $15,000 in loans to the bank. She needed more money to do some fixing up in the bar before she re-opened it and she was now about $30k in debt. Business was not real good. She managed to keep the bills paid but little else more. So now the bank was threatening to foreclose on her. The guy that came in tonight was a process server who served her with the papers for the lawsuit with the bank.
She looked at me with tearful eyes and said, “I don’t know what I am going to do. The bar is all I have. If I lose it I will be out on the street in a matter of days”.
I reached across the table and took hold of her hands. “Jo, I would like to help you out if you will let me. I have managed to stash away a nice chunk of change for the proverbial rainy day. I think this is the rainy day I have been waiting for. I would like to take care of your $30k debt and I would also like to invest another $50k to help make repairs and do a renovation at 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 chuckled. “Three reasons. First, I like your place. It is the friendliest place I have ever been to and there’s no way it should have to close. Second, I have always wanted to own a bar. Mostly so I could drink for free but also because a well run bar is a great investment. Third, and most importantly, I have fallen hopelessly in love with you and I would do anything to help you out and bring that beautiful smile back to your face.”
As I spoke to her I looked directly into her eyes. When I hit the third reason I saw not only a look of sheer surprise but also just a faint glimmer that told me there might be something mutual there.
She looked and me and said, “You’re serious, aren’t you?”
I told her absolutely yes on all counts. She asked me what the catch was. I told her no catch other than she’d have me for a partner. The bar was still hers to run as she liked. She’d just see me a bit more frequently and I got behind the bar privileges. But now she wouldn’t have to worry about the debt putting her out of business.
She thought about it for a couple of seconds and then said, “For the life of me 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 was beaming from ear to ear.
I looked at her and said, “That beautiful smile makes the investment all worth while.”
We sat in the booth in a happy silence. After a couple of minutes I asked her if I could walk her and she happily agreed. When we stepped outside we discovered that the rain had stopped. As we walked, I took her hand in mine and eventually put my arm around her. She snuggled right in like she was made 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 responded by pulling me close and kissing me hard and sliding her tongue through my lips. She asked me if I’d like to come in for a nightcap. I said sure and followed her in.
Once inside she turned around, put her arms around my neck and kissed me again. This time we swapped tongues and I took her in my arms and pulled her close. My cock was about to bust out of my jeans as my hand traveled down her back and began to kneed 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 right 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 tighten up and she backed away from me.
“Bob,” she said. “I am afraid that I am not the woman you think I am. I find you incredibly attractive and sexy and I want you with every fiber of my being, but I can’t lead you on without telling you the truth”.
I looked at her with a very quizzical 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 I expected to find, I felt a lump very 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. Jo, this incredibly sexy, loving, caring woman was actually a guy.
I looked her in those 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 will understand,” as she looked down towards the floor. I thought for about half a second and realized that I really was smitten with this woman and I didn’t care about what was between her legs.
I tilted her head back and kissed her softly on the lips. “Jo, I fell in love with you the moment I saw you. Nothing is going to change that. I will leave if you want me to but I will 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 began to nuzzle and nibble 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 shove that caused me to fall back onto the bed. She pulled down my zipper and fished my cock out of my pants and took it in her hand and began to kiss it and stroke it ever so gently. I leaned back on the bed and moaned as her hand and her lips felt so good. She leaned her head down and began to swirl her tongue around the head of my cock. This made me shudder and twitch which she took as a sign to continue. She licked up and down my shaft and finally took it all into her mouth. She sucked me like there was no tomorrow and within minutes; I shuddered and shot my load of hit cum into her eager warm waiting mouth. She continued to suck until I was dry and clean and the she stood up between my legs.
I smiled at her and reached over and undid her jeans and dropped them to the floor. I helped her step out of them. My face was right at crotch level and I could see the bulge in her panties. I grabbed the waistband on each side and slide them down freeing her clitty. It was about 6 inches long, circumcised and not as thick as mine. I stared at it briefly and then leaned my head over and licked the head.
Jo moaned and I reached my hand out and took hold of it. I had never held or touched a man’s cock other than my own, but somehow this just felt so right. She was completely hairless around her cock and balls. Her cock, though hard felt soft and wonderful in my hand. I licked the head and began to stroke it ever so gently. Jo moaned and I began to swirl my tongue over the head as I had felt her do to me. Jo took hold of my head and began to thrust her hips and fuck my mouth.
I tightened my grip on her pretty cock and began to suck on the head with all the gusto I could muster. Hearing her moan and feeling her cock twitch 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 beginning to tighten. I stroked faster as I sucked hard and suddenly she let out a moan.
“Ohhhh…baby…I’m gonna cum!" I locked my mouth over her cock and sucked harder still. I was rewarded by a nice hot load if cum. I sucked it all down, finding the taste not at all repulsive. In all honesty, I loved the taste. It was sweet and salty and I knew I want lot and lots more. I sucked her until she stopped cumming and pushed my head away.
We both finally undressed and crawled on to the bed. I took her in my arms and kissed her on the lips while I stroked her hips. She had my cock in her hand and looked me straight in the eyes.
“Are you sure you still want to stay?” she asked me.
I chuckled at her, grabbed her cock and kissed her on the lips. “Jo, I’m not going anywhere until you tell me to leave. And even then I might not leave. I told you that 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 like. I have 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 over so we could spoon. My cock was beginning to harden again so I slid it into the crack of her ass and put my arms around her and gently caressed her breast.
I smiled and said, “Let’s just say it makes things more interesting but doesn’t change my feeling about you.” She smile and we cuddled in the bed and fell asleep in each other arms. The best night of my life was about to get better and hopefully last for a long, long time.
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