I e-mailed some online gay friends asking for the name of a place someone like me, a bi-curious middle aged guy, would be comfortable in just having a beer.
They e-mailed right back with the name of a place called Charlene's near downtown. Before I had the chance to wonder why the place was not in the gay part of the city they followed up with a note that said it was not a gay bar per-se but a nice place that catered to a wide variety of professionals. They were comfortable there.
I had been curious about the "far side" and wanted to start exploring that end of the planet. I had expected them to give me the name of a gay bar but thought their suggestion was better, allowing any decision on my part to be delayed.
I sent my thanks and the following Friday made my way to Charlene's.
I had been a widower for two years and had been nagged about getting on with my life for one. I had taken a few steps towards that goal but had not been able to drum up much enthusiasm in the pursuit. Cruising the Internet had become my main pastime. That eventually led me to gay sites, which in turn piqued my curiosity.
The happy hour crowd was leaving and the evening crowd had not yet arrived at Charlene's so there were few people in the place. The band would not be on for an hour. I sat at the bar and ordered a beer. The bartender was a large woman with large tits that were just barely contained by her halter-top. She asked me if it was my first time there and after I admitted it was she pulled her top down and allowed her tits to spill out.
"Just wanted you to see what you would miss if you did not come back," she said.
I licked my lips and assured her just for her I would be back.
She leaned over the bar and kissed me on the cheek then went to attend to a customer. Her tits stayed out until the outside door opened and new people came in.
I wondered how she figured out it was safe to display for me.
The jukebox was playing seventies rock, the joint had cold Dos Equis, smoke free, big tits for entertainment, grown-ups for a clientele; I had found a new home.
The first guy to come over to say hello was a guy setting up for the band. He welcomed me and said he hoped I liked their music. He turned out to be the lead singer for the band. He did not look or act gay but something told me he was.
The second person to come say hello was a willowy Latin woman. She was very pretty, very sexy. We flirted for a bit until the bartender pointed at her crotch and pretended to be jacking off a dick.
I leaned closer to the "lady" and asked, "Is there a dick under that dress?"
She seemed defensive as she answered, "Yes, there is."
I kissed her on the cheek and told her how terrific she looked.
She exhaled and kissed my cheek then told the bartender "I like this man. I would let him do unspeakable things to me. Often.
She kissed my cheek again and went on to other conquests.
The bartender said, "When in here she is Rita. Outside she is Richard, assistant district attorney. You have just gained a useful and faithful friend. This beer is on me."
She obviously liked Rita and my reaction to her must have been perfect. Charlene, (the bartender and I would later learn also the owner), had apparently pegged me as a courteous and gentle heterosexual. I guessed that was about right. I could also tell that she thought she should know who I was.
As the evening wore on it became clear that most of the people there knew each other. I asked Charlene and she said that each night had its own characteristic crowd, a group of regulars, so new people such as me were easy to spot.
They were closed Mondays and Tuesdays was unadvertised ladies night. She suggested I needed to make an appearance some Tuesday.
Wednesday seemed to have become metrosexual night, (she said that with some distaste). Thursdays and Fridays were hodgepodge nights where everyone of every ilk showed up. It was fifty percent bisexual or gay/lesbian and the rest were straights, many with gay friends. Saturday was date night with predominantly straight people.
As Rita swished by she gave me another kiss on the cheek while her hand rested on my thigh. She did that on every trip past me, her hand getting closer and closer to my crotch each time.
Charlene said I had a decision to make; Rita wanted me for the night.
I told her that I had unfulfilled gay fantasies and Rita may be a way to put my toe in the water, so to speak, but I would hate to lead her on then back out.
Charlene nodded and excused herself; it was time to introduce the band. She and the band were well received. When she returned she took my hand and pointed to an unoccupied table in a cubbyhole past the stage saying, "I'll send you a beer shortly."
By the time the band got it going the place was pretty full. I noticed a couple standing by the back wall and I invited them to join me at the table. As soon as we exchanged greetings Rita brought me my beer and sat next to me. The couple greeted Rita warmly and in their eyes I ceased to be a stranger. Rita and the woman immediately went into a conversation while the guy and I listened to a very good cover band and drank our beer.
During the first band break the guy, (his name was Sam), caught my eye and in whispers wanted to know if I knew about Rita. I nodded yes and said, "Nobody is perfect."
He laughed uproariously at the old line which he passed on to his lady, (also called Sam), who in turn passed it on to Rita who gave me the best "Well I never..." look I had ever seen.
The three of us laughed as Rita extended her very funny "I have never been so insulted act" which continued until I kissed her on the cheek.
She went through an "I should know better but you are forgiven" routine then kissed me on the cheek.
It was probably because I really liked Rita and was thinking of her as a "she" because after the second band set started I asked her to dance. The third song was a slow song and I started back to the table but Rita held me to her, so we danced. Half way through the dance Rita whispered in my ear, "Is that erection for me?"
I said, "What erection?" and pressed it onto her thighs.
The song ended and when we returned to the table Sam and Sam were in the midst of a passionate kiss. After sitting Rita pointed to where Sam's hand disappeared under Samantha's miniskirt. Her own hand settled on my erection.
The second and last band break allowed us to quietly talk while Sam and Sam masturbated each other. Rita's hand was caressing my dick.
" I know you are straight but I know you like me even knowing what I am. I also know you would be OK with me giving you at least a handjob. My hand and your dick love each other. I stopped asking men to come home with me two years ago when I got beaten up for my efforts. I have no fear of you and I am asking you now to please come home with me tonight."
I did not know what to say. I did like Rita and would think less of myself if I hurt her feelings. I loved her hand on my dick.
By way of an answer I kissed her softly on the lips and said, "Lets go."
We said goodnight to the Sam's then we both kissed Charlene on the way out and she seemed very pleased to see that I had opted for adventure.
I followed Rita to a smart-set townhouse building near the baseball park. As soon as we sat on the sofa we began to make-out and she resumed caressing my cock. Three minutes later she had fished it out and I felt her warm hand gripping it softly. I may have scared her a bit when I stood up but what I wanted to do was lower my pants and shorts, I needed more comfort. As I stood in front of Rita naked from the waist down she grabbed my dick and kissed it. She waited for my reaction, which was to step closer to her. She rubbed my cock on her face and kissed it until her lips wrapped themselves around my cockhead. She again waited for a sign from me, which was again to step closer to her.
My cock slid slowly into her mouth. Rita looked like a woman that had been denied her favorite candy during a long torturous diet. She loved my dick in her mouth. I took my shirt off and was now nude for her. Her hands softly gripped my ass.
I was so into the blowjob I knew I would not last long. I signaled Rita but as I expected she kept me in her mouth until I was drained. I sank into the sofa and kissed her passionately, tasting my cum in another's mouth for the first time in well over two years.
Rita held me tightly and rained kisses on me.
I put my hand on her crotch and she froze.
I kissed her softly while I caressed her bulge.
I told her I wanted to meet Richard.
Anxiety clouded her face as she stood and went to her bedroom. I waited for Richard on the couch. After a few minutes a nude man joined me. He was in his early thirties, had a small frame and a small dick. There were small tits on his chest and there was not a single strand of hair on his body below his head.
"Hi, I'm Richard," he said in a definite masculine voice.
I stood and shook his hand while I introduced myself.
It occurred to me I had never introduced myself to Rita.
What transpired over the next hour or so did not strike me as somewhat bizarre until days later. Two naked men that had just met sat on a couch and talked about jobs, baseball, drinks, restaurants, until they were fast friends.
Without telling me I understood that Richard was basically straight, Rita was of course a woman.
After he yawned I decided to leave and go home. He told me to hang on for a minute and went to the bedroom. Rita came out about three minutes later wearing panties that did not completely hide her bulge. I took it as a sign of trust because she had not bothered to go through the routine of hiding her assets and had opted for comfort.
She told me it was unsafe for me to go home when all the drunks were driving and I was welcome to spend the night with her. She took my hand and led us to her bed. We cuddled and kissed, my hands caressing her small tits, hers caressing my dick. The long day and evening and the beers conspired against me and I soon fell asleep with Rita in my arms.
The following morning I awoke spooning behind Rita. My hard dick was inching its way into her ass. My cock was wearing a condom. Apparently my dream of someone loving my dick had been real. I signaled my wakefulness by grabbing Rita's hips and pulling her back towards me, burying my cock deep into her ass. That accomplished I wrapped my arms around her and kissed her neck and shoulder. She moaned.
I began a slow thrusting into her that she immediately returned. We were at cruising speed when my hand worked its way to her penis. She stopped her thrusting and her hand went to mine.
I whispered into her ear, "This is the biggest clit I have ever had a chance to play with."
She slowly released my hand and allowed a deep sigh to escape. Her arm went behind her and she grabbed my ass. She turned her head for a kiss and the fuck resumed.
I used two fingers and a thumb on her large "clit" and though it became firmer it never became fully hard. I increased my speed on both sides of her, very much enjoying everything I was doing.
Rita began a low moan; I began to work as fast as I could. My orgasm was electric. I may have bitten Rita's shoulder. I was in the midst of catching my breath before I noticed Rita had cum in my hand. I kept my hand over her groin and my dick in her ass until it plopped out. We both voiced our disappointment over that. She turned to me and kissed me with great feeling, sat up and removed the condom. She swallowed my dick briefly before leaving the bed.
The flush of the toilet guided me to the bathroom and I went to piss. Richard was in the very large shower. After my piss I joined Richard under the spray while saying good morning. We were again just two guys in a shower after a morning workout. We chatted as we dressed, he had a meeting at the mayor's office, and I had a lunch date with my daughter and her partner. Just before separating to head for our respective cars he handed me a business card, Richard's title and phone numbers were on the printed side, Rita's cell phone number was handwritten on the back.
He said, "Don't be a stranger."
"No chance of that," I replied.
My lunch date was great as usual. My daughter and her partner Clara were schoolteachers and kept trying to get "poor babies" out of me because of the imminent end of their summer vacation. They had been partners for ten years and none of us could see that ever changing. I was happy that my daughter was happy. I adored Clara too.
On a whim I asked them for a date for the following Tuesday night. I told them I had a new hang out I wanted to show them. They eagerly accepted and both expressed hope that I was at last getting out of my mental dungeon.
As usual my smile lasted a long time after we said goodbye. As I found myself wondering what to do with a Saturday night my sub-conscious already knew, I had already dialed Rita's number.
A whispered "yes" answered and I said, "You need to program this number on your caller ID. It may save you some anxiety."
Richard said, "Consider it done. Anything else I can do for you?"
"Yes, I was wondering if Rita was available for dinner and dancing this evening."
"Yes, I am positive of that."
"Pick up around seven?"
"Yes, that would be agreeable."
"Thank you Mr. D.A. See you later."
"Yes, thank you. Good Bye."
I had to chuckle at his act, accepting a date for Rita in the midst of a meeting with city officials.
That evening we dined at a steak restaurant with a great and well-deserved reputation. I took us back to Charlene's after dinner. Rita seemed a bit nervous; she said she had never been there on date night.
Rita was not just passable as a woman, she was a woman. There was no trace of Richard even though she wore very little makeup. I was on a date with a sexy lady.
Charlene was surprised to see us walk in. We got big kisses from her and introduced us to her Saturday bartender as dear friends, which apparently indicated our drinks were on the house. I was never asked to pay and when I asked for my tab I was told, "it had been taken cared of."
The band knew Rita of course and the Sam's were there and insisted we join them at their table. No one gave us a second look except to wonder at the difference in our ages, (I was more than ten years older).
We danced, we laughed. Half the band joined us during their break, which apparently enhanced our standing among the crowd.
As the evening waned and the crowd dispersed I found myself kissing and finger-fucking Samantha while Rita kissed and masturbated her husband.
I took Rita to my house and we fucked the night away. Sunday morning Richard had services to attend so I drove Rita home.
She asked me if I had Friday night free. I said I did. She said Sam and Sam wanted us for a foursome that night. She was hoping I would agree.
The following Tuesday I took my girls to Charlene's. When I introduced them to her as my daughters her confusion was short lived considering I was introducing a tall blonde and a diminutive black girl. She leaned over the counter and in a conspiratorial whisper said, "Quick suck on these" as she released her tits from confinement. Clara hesitated for a second but my daughter immediately clamped her lips on a nipple and bit it gently. I had to boost Clara up a bit so she could reach the offered tit but soon followed suit. Charlene seemed very pleased that I though well enough of her and her place to bring my kids in.
Tuesday night turned out to be lesbian, bi fem, and couples with bi curious women's night. I had not noticed a doorman when we came in but it turned out single men had an exorbitant cover charge to enter.
There was no band but Charlene did have a DJ. The girls had a blast. They even introduced me to another parent that was there with her daughter. The woman and I danced and sat together while the girls exhausted themselves on the dance floor. Her name was April.
The DJ took a break halfway through the evening and put on a disk of slow songs. By then pairs had been formed and everyone was on the dance floor. I danced with Clara and with my daughter and then with April. As one song ended and another began she pressed her body against me, ran a hand to my very erect cock giving it a squeeze and said, "I see you are not gay."
"No but I am working on it."
She giggled at what she assumed was a line, " I feel like cock tonight. Are you available?"
"Depends on transportation logistics. I drove my daughters down."
"I came in my daughter's car. Do you by any chance live on the south side of town?"
It turned out they lived twenty minutes away from my house. If I could get her home by six AM she could make it to work the next morning. As she said that her hand was griping my cock over my trousers. It answered for me, "Deal."
April looked at my girls as they swayed together on the dance floor and asked, " How long have they been together?"
After I told her she commented, "That's longer than my marriage."
She continued to caress my dick as I caressed her ass.
She suddenly pulled away and hurried to her daughter. Her girl was sick and obviously in no condition to drive.
My evening fuck vanished.
Before she left April gave me her phone number and told me that if I did not call her she would break into my house and take me against my will.
I kissed her and said, "I really look forward to that."
My girls and I left at a mostly decent hour. They were mildly curious about what happened with April but I assured them she was not a lost cause. They thought that deserved a high-five.
That Friday I fucked and ate my first new pussy in ages, Samantha's. It was fabulous.
Sam finally got his cock into an ass. His wife had aborted their one and only attempt at anal. Rita admitted that she had wanted Sam to fuck her for a long time. Samantha said that her husband had her permission to fuck Rita anytime he had the urge as long as she was there too.
Looking at me she said, "I wont cheat on Sam but if we find ourselves in this situation again I would welcome your dick into any part of my body, except one."
We laughed at her unnamed exception as we untangled ourselves from each other to go home. We had shared our group sex for over two hours. Richard had an early plane to catch so I declined the invitation to stay the night.
That Saturday night I had every intention of taking April dining and dancing but she insisted we go to my house, fuck, order pizza, fuck, watch a DVD, fuck, sleep, fuck, eat breakfast, fuck, return her home. I barely managed to comply and was relieved when she said it would be a month or two before we did that again. She was true to her word.
Rita and I became occasional fuck buddies; Richard and I became good friends and attended baseball games together on occasion. It was amazing to me at first that I thought of them as two separate people. Soon that became the norm.
Foursomes with the Sam's and April fucks became pretty much monthly affairs.
Eventually an all male foursome at Rita's place satisfied my last bit of curiosity about the far side. But that is another story.