Baggage and Fantasies Ch. 01

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Oca 4, 2023 // By:analsex // No Comment

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Today was my personal anniversary. I was celebrating 30-16-6-3 and six-months. Confused? It’s easily really, for thirty years I’ve been married; for sixteen years I have been the care giver to my disabled wife; it has been six years since my wife and I have had sex; it has been three years since I tried to find relief with and escort and found it is not my style; and it has been six months since I began trying to give up on sex in this lifetime. The last six months have been an interesting experiment. There has been less pressure but I’m lean, healthy, playful, a big tease and still seem to be greatly attracted to women more than I should be at my age. My age has helped. As long as I go to places where the women are under fifty, I am seen as the cute, harmless, old-guy. Whether in business, shooting pool, building houses or pleasing a woman, I’m about as harmless as a swarm of yellow jackets. Still as the saying goes, “It takes two,” and the ladies have sent me home alone for a host of excellent reasons.

One beauty at the local bar, I have been trying to impress for five years. She showed some interest, has made out with me and let me get her off with my hands a few times but is really turned off because I am married. She knows I will always accept the responsibility of taking care of my overweight, over-medicated and wheelchair bound wife. It was about her hundred and fifteenth rejection that pushed me to try not flirting with the ladies any more.


My cell phone was playing some unknown tune when my skill saw spun to a stop.

“Craig, this is Ann Winters, you had me be you partner at pool last Thursday night.”

“What a pleasant surprise. I don’t get many calls from beautiful women.”

“Thank you, but you are as full of blarney during the day as you are at night.”

“Alright, since you didn’t like that compliment, how about, “Oh, the short, sexy woman with the large breasts and the tiny waist, who was my partner when we whipped the noisy asshole and his wife””

“Oh, I like that description. However, I broke twice and never had to shoot again.”

“Are you ready to challenge the entire club this time?”

“No, I was calling to see if you wanted to go for coffee some morning.”

“Only angels get up early in the morning and offer to buy coffee.”

“I’m pretending to meet that requirement.”

“Pick the place; I’ll drive half way across the state to have coffee with you.”

I was truly surprised by Ann’s call. I had drafted her from a nearby stool, when asshole and his wife arrogantly accused everyone at the bar of having unmarried parents and stating that no team could possibly be as good as him and his wife. Ann and I kidded and exchanged non serious bar banter for an hour after the contest. It is usually easy to defeat a drunk, especially after he insulted me twice for refusing to play for money. I had watched him play three games before accepting his taunts.

Ann is about 5’1″ and was the classic “spinner” once. Now she is about 50, carries an additional thirty pounds — mostly in her breasts and ass. Her face shows her age but most thirty- year old women would envy her body and her grace of movement. I had never seen her at the bar before. Several of the young hunks started coming on to her and I found an excuse for her to escape from me. Her tight jeans and tube top screamed “Cougar,” so I was avoiding rejection.

At the coffee shop, I returned from my second trip to the little boys’ room offering a defense, “Taking a water pill in the morning means I make two relief trips for every cup of coffee.”

“I don’t have that problem, but that slice of pie would go straight to my thighs and I would waddle around work every day and none of the single men would pay any attention to me.”

That line hit me like a ton of bricks. I never had any secrets. Everyone at the bar knew my situation. Quite a few of the patrons and employees have been to my house and have met my wife.

“What’s wrong, Craig? You look like you’ve seen a ghost.”

“No, Sweet Thing, I look like I’m thoroughly enjoying coffee with a lovely woman and just realized that I may have made a horrible mistake and may have hurt you.”

She sat and looked like a deer caught in the headlights.

“I have gone to the same bar with the same people for a long time. Everyone knows me and my situation. It did not occur to me that you do not know about me.”

“I don’t know what you are talking about.”

“First, I’m sixty, I build houses for fun, I’ve been retired for many years, I’m very playful, and I am the primary care giver to my disabled wife. Ann, I never had any intension of keeping any secrets from you but I am married.”

She was shocked but recovered quickly, “Tell me about your wife.”

I felt like shit and I’m sure it showed and reflected in the tone of my voice. “She has a form of Parkinson’s, is in a wheelchair and is heavily medicated. People at the bar have known for years; it did not occur to me to tell silivri escort you.”

“You agreed to have coffee with me.”

“Yes. It is a great ego boast to have a lovely woman ask me out for coffee and to think she might find me interesting. I have tried and failed dozens of times to find a female friend who understands the responsibilities I have accepted for life. I have never slept around although my wife has urged me to find someone to meet those needs for years. Escorts are not my thing. Please forgive my oversight and know that I was truly excited by your invitation.”


“Wrong word. In our short time together and our phone calls, you were so much fun and I felt good talking to you. I started reconsidering finding a friend with common interests to do things with, travel with and just have fun with. I gave up on such things because of my “baggage.”

Our coffee time was cut short. Ann was definitely put off by my admission. My third apology bounced off her closed car window as she drove away.

I did not feel good about myself for the next few weeks. Ann had been a delight. I had foolishly, for the hundredth time gotten my hopes up. I had not thought enough about her and I had hurt her. I just stayed busy building my current spec house and working around my own house to get everything done that spring requires.

Tired, dirty and with a flatbed full of lumber to frame a two room and bath addition on a house I had built ten years ago, I stopped by for a beer at the bar. Brandy, one of the luscious married strippers who I drool over, wrapped herself around me before my eyes adjusted to the darkness inside the bar.

“Where have you been? I’ve missed you.”

“I’ve missed your greetings and your anatomy lessons. Text me your schedule and let’s get back on track for you to give me a table dance once a week. How are your husband and little ones?”

She had to scurry off; it was her turn at the rack. I settled down at the bar for a beer and got greeted by two more dancers. It was just after shift change and one cute little bartender named Sara said, “I want a hug too, but you are a mess.”

“I’ll promise you a good tip on your next shift if your overlook my dirty shirt and squeeze that lovely body of yours into me before that tall and gruesome boyfriend of yours shows up.”

“He’s not gruesome.”

“Well, he’s not my type.”

I got my hug. Usually, I cleaned up after work before coming to the bar. Slacks and a nice clean shirt were my usual attire.

I got a tap on my left shoulder and turned to face Ann. “All the girls in the bar get a hug accept me?”

“My glasses are in the truck. I would never have missed you on purpose. I am surprised that you want a hug from me, however.”

After a friendly hug where those lovely breasts reminded me that my equipment still works, we moved to a tall table with stools as far from the oversized, overdriven speakers as possible.

“Craig, I’m sorry for my reaction when we had breakfast.”

“It was understandable.”

“Sara told me a lot about you.”

“You hanging out in the bar? Bartenders are supposed to be tight lipped.”

“She comes in for breakfast where I waitress. It is on her way home after she drops her daughter off at school every day. Business is pretty slow then, so we get to talk.”

“Did she tell you about the axe murder charges and wild month long parties where we sacrifice a virgin?”

Ann’s smile convinced me that all was forgiven. “She told me that she met your wife once and a little about your bar history.”

“I’m doomed.”

“Not really. I was being somewhat of a hypocrite.”

“You are too pretty and desirable for that. Just looking at you makes my mouth water.”

“I’m trying to be serious. I’ve been separated for almost three years but my divorce won’t be final for another month.”

“I was serious. We all have lives. When we get a little age on us, stuff has happened that complicates things. Please hand me a napkin; I am trying to be attentive, but I am drooling.”

“Over me?”

“First time I met you, we shot pool, but you were dressed like you are tonight and all the young studs were coming on to you. I didn’t think you would want to use your time talking to me so I sought an out to keep from being pushed away.”

“I met Brandy; she told me where to find your porn stories and how you have helped several people at the bar.”

“I am going to have to give that cute little butt a spanking for talking too much.”

“I read a lot of your stories. You write well.”

“I had rather hear that you were turned on by my stories and got very wet.”

“Why? Is the oral fetish that runs through many of your stories true?”

“Yes it is, and with you I would hope you squirt and get wet enough to drown me.”

Ann’s face was red and she had forgotten to exhale.

“Did I get too naughty? I always seem to be apologizing to you.”

“I was warned that you will say about anything bakırköy escort and have gotten to several of the dancers here.”

“”Gotten to?” What does that mean?”

“Several told me which story was written especially for them. A couple admitted to playing out verbal fantasies with you during table dances in the corner. I’m not sure what they meant but they seemed to like them.”

“Ann, now I am embarrassed. I had no idea you ladies talk and share so much.”

“I was here on a rainy slow night and I was the only customer who wasn’t playing video crack. We talked; don’t get a big head, not everything was about you.”

“Damn, put in my place just when my ego was soaring. I am curious; I thought I really turned you off.”

“Often I need a male friend to just go out with for dinner and a movie. I got to thinking and your situation sounds very real, honest and familiar.”

“Ann, I don’t lie and won’t try to trick you to get into your pants. I’m too old for those games. I’ll be honest, open and playful. If anything ever happens it will be something we both want. I did not lie to you; I haven’t been with a woman in several years.”

“Your stories are so alive, vivid and hot, that is difficult……..”

“Don’t say too much. I have a great imagination and could turn you inside out if you were in the mood to let me. My problem has always been in finding the right woman who wanted to be with me.”

“How about JP? Everyone says you are head over heels for her. “

I was quiet too long before answering. That answer was personal and not playful. I was considering not answering.

“Craig, I didn’t……..”

“Ann, let me try to answer. I like you and want to let all the chips fall wherever they honestly fall.”

“OK, I’ll stay quiet.”

“I fell hard for JP, years ago. If she is what I think she is away from this bar, she is exactly the kind of woman I would love to have as a friend, companion, work partner and lover. She has been a stripper for so many years, her perceptions are distorted and she has a perfectly formed set of rules that work for her. I think she likes me too but has kept me at bay for years and always will. The people at the bar kid me because of how I look at her. The situation is, has always been and will always be one sided. I know that, accept that and have moved on. You did the perfect thing to attract me. You called me, showed some interest and pursued me. You made me important and made me feel desirable and manly. I thank you for that.”

She started to speak but I continued my speech. “Ann, the women who work in places like this may enjoy my company some but they are here for my money. It is their job and I have enjoyed playing along for the fantasy and relief it provides. I have always wanted a healthy woman friend who cared about me as well as my wallet. I still want that, but have generally given up because of my age and situation. Again I apologize for how things were not communicated properly between us but it was all an honest mistake.”

“I’m not a little girl or one of your young or jaded dancers. I came into the bar thinking I wanted a young buck to make me feel twenty-five again. They bore me. You don’t. Let’s start over.”

I was shocked but very pleased. For the next three hours the busy, loud bar did not exist. We talked, discovered our common interests and where we differed. She agreed to be my date occasionally for events like business functions, museum show openings, a picnic, a walk around the rose gardens, Cinco de Mayo, wine tastings along the river, art and craft shows, etc. I had looked for someone for many years to do these things with. It was surreal to be looking at a beauty who wanted to do these things with me. I did not ask, because I did not want to hear the answer of why she would go with a man fifteen years her senior and not truly handsome.


The grassy fields along the river were filled with carnival rides, tents, food venders, craft sellers and ten different Mexican songs playing at one time. It was cool and cloudy, as it often is in Portland, but it was the “Fifth of May.” I had lived in Portland for six years and always wanted to go to the Cinco de Mayo celebrations but never had attended even one event. I always wanted to go to the Rose Show events but never did. I am a member of the Art Museum and the zoo but have never been to either. This had been a horrible pattern for years. Now, I was on my way to pick up Ann and as nervous as a sixteen year old boy going his first date.

Ann’s one bed room apartment was furnished with rental furniture, thrift store items and some things that came from a nice home. She responded to my silent appraisal, “My ex left me with a mountain of debt and no bank account when he split with his most recent bimbo. I’m still recovering but getting there.”

“I ran out of money trying to get through college, dropped out a semester to work and got my draft notice. Before I dropped out, şirinevler escort I would go to a diner, get the catsup containers off several tables, order a bowl of hot water and make tomato soup. It wasn’t very good and always made the managers mad.”

“I don’t believe such things are your problem now.”

“I have other issues, but money is not one of them. Help me not be foolish and keep me sane and we’ll have a great time.”

“Sometimes I feel like I’m losing it too.”

“You don’t want me to tell you what I have decided to prescribe for myself when I feel that way.”

Ann tilted her head back and laughed hardily. “You and I think alike. I’ve had the same thought.”

“I want to die gasping for breath so sexually satisfied, I don’t really care.”

“Do women really pass out, like in your stories?”

“They can if they are smart enough, can turn their minds off and let their bodies fly, go higher, then higher still.”

“What a nice thought, if only it were possible.”

I did not respond. Maybe she would let me repay her wonderful gift of being with me and letting me enjoy her company so. I felt young, desirable and sexy – feelings that I had protected myself from for three years. Feelings that I thought I had let go for this lifetime.

For the day we dodged raindrops, ate gassy foods, drank too much, danced poorly and laughed more than either of us had laughed in years. After four beers, I raced to hide under the edge of a vendor’s tent to avoid some rain, but I stopped faster than she did. Her body crashed into mine and she looked up into my eyes. There was no thought, no plan, no demand, I held her and kissed her. Her lips opened and I sucked at her tongue. Mine followed hers when it retreated and she returned the favor. I held our close position and finally sighed.


“I felt that and it felt good.”

“What do you mean?”

I thrust my half hard cock into her hip, pinning her tightly against a support post.

“Oh, I see.”

“Was it only me, who felt anything?”

“No, but I don’t have anything to push into you.”

“Yes, you do.”

Her body hesitated, turned slightly, her legs opened wider and her hips tilted and pressed into my thigh. I kissed her again. This time our lips were soft and crushed into each other; our tongues dueled to feel excitement, sense passion and enjoy tastes. I could feel the moist hot grind on my thigh from her spread pussy.

“If you are a friend you will only move slightly back and will stand there and talk to me for a while.”

“I can do that, but why?”

I took her hand from my neck and slid it slowly down the front of my body. As she felt my right nipple, she was trying to guess where this conversation was going. I slid her hand even lower, stopping over my belly button and her finger tip wiggled into it. I pushed her hand down again but only to urge her. She continued the movement and closed her fingers around my twisted hard cock. Her fingers squeezed.

“If you move, everyone will see what your body has done to me; how it has taken control. They will see that I want you and am ready for you even though there are twenty thousand people here to watch.”

The little vixen let her fingers linger, massage me and then she stepped to one side, looked down to confirm my admission and exposed my excitement to the world. I did not seek to cover myself but leaned in and whispered so my breath would tickle her ear.

“Someday sexy one, I will lift your skirt and let the cool wind hit your sweaty, satisfied pussy and let the people see our cum run down your legs.”

Her eyes closed, her breath deepened, her body leaned into mine and her hand worked my uncomfortable cock. Her voice was barely above a gasp, “Would you do that horrible thing to little innocent me?”

I switched ears so my body would block my hand cupping her breast and capturing a nipple between my fingers. “Yes, I am afraid I would do that to you. I also must warn you that I would do so very much more. I would hope I could do most things with you, but if you want, I will pin you and I will do them to you. Your make me hot and crazy for you. I could easily spread you and take you.”

She was in her fantasy – I had hoped, I would find it. Her eyes were still closed. She kept her ear next to my lips and talked to my neck. “How would you do that?”

“Right after sunset, a cool wind would come up. You would stand in the middle of a crowd; you would tease and challenge me by reaching under your skirt and stepping out of your warm, damp panties and handing them to me. I would use them to inhale you, get very turned on and not care about anything else in the world except your body. The scent of you would make all but you disappear. I would guide you toward a bench in the shadows and push you over it, stand behind you, take my cock out and slide it between the wet lips of you wonderful pussy. I would thrust into you until you begged me to stop because you came and came and she was very sensitive. I would sit on the bench and hold you, comfort you and slip my cock back into you. You would feel it dance in your belly and struggle for control so my body would not pump into you and fill you.”

Ann’s eyes were squinting, her face contorting. “Craig, you must stop. You are going to make me cum.”

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