Over Fifty Housing – Writers

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I am a 60+ year old bi woman. Many of my stories, originate in memories and recent events of my life. All contain a combination of real and fictional characters with names changed as appropriate to protect the guilty. They are memoirs spiced with a kinky imagination. I am submissive by natural inclination in most relationships, most often extremely submissive in sex.

If you like kinky mature women I hope you will enjoy my stories and comment on what you liked and perhaps didn’t like to help me improve. I sometimes, to better frame the scene, include passages from stories I have previously published here on Literotica.

In this series I write as Doris Sweeney a White, widowed, bisexual, 53 year old woman.


My part time job in the sales/leasing office at OFH has made my social life interesting. I met Ron when he first looked at homes here as a place to move to in retirement. Months went by and one day he showed up at my office as a new resident. He bought one of the model homes about three months before without me knowing. We sat and talked about life at OFH and eventually he asked me to join him for dinner. There was something about him, something that didn’t quite fit my expectations for an attractive retired man. A little too well groomed, a little too neatly dressed, a little too polite? It was not any one thing but a combination. Oh well, I’ll figure it out, I’ll figure him out.

“Your choice” he said, so three days later we headed to my favorite Italian restaurant. Ron began his story at dinner and it continued in my living room over a dessert wine. I told Ron about my life before I moved to OFH and my family but avoided the subject of Val and any obvious discussion of sex. (Read about Val in OFH part 1 — 3) Ron explained that he and his wife owned their own business and never had children. His wife died in an automobile accident when she was forty-five. He dated over the years but never remarried.

As we talked we discovered that we both enjoy writing, Ron is actually a published author. For both of us what started as a casual interest and a way to record memoirs became more important and a way to interact socially with people of similar interests. Ron suggested it was also a way to vent unfulfilled fantasies. I bit my tongue and did not elaborate on my own leanings toward fantasy and erotica.

In the end, however, I couldn’t resist a tease, “Why Ron, what do you mean fantasies? Do you mean adventures or travel?”

He did not answer directly but offered, “I have always belonged to writers groups and also enjoyed meeting other writers as much as I enjoy writing.” He continued, “Doris, maybe we could start a writers group here at OFH.” I allowed my original question to go unanswered.

We agreed to give it some thought and then discuss it again at dinner the following Friday. He suggested that if we form a group we might ask people to write a story based on a prompt like writers workshops sometimes do. We agreed to be our own writers group guinea pigs when we decided on a first prompt, his suggestion, “Write about something you greatly regret.”

We left the conversation agreeing that we had two weeks and only two weeks to finish the story and we would then meet again to discuss the stories and the writers grouped . In the meantime I sent out a “Writers Group Being Formed” notice to OFH residents to see if there was any interest.

I almost immediately heard back from Lynn, a woman I met when she first moved in, and Olivia a new unknown woman and George a retired school teacher, also new to OFH.

My contribution to this Ron and Doris only first exchange was a difficult choice. I did not particularly want to reveal personal information quite yet so I decided to write the story as fiction.

Sure it was a twist on the prompt but call it writers prerogative. After that decision the story itself was simply and adaptation and consolidation of other stories I had already written.

REGRETS – a work of fiction.

Sara’s middle child, her only daughter El, caught her looking at another woman, a stranger, in a coffee shop. She asked if Sara was checking the woman out. Sara answered, “Of course not, El. Don’t be silly. Well maybe, what about it? She was very attractive don’t you think?”

El then asked, “Mom, tell the truth, have you ever?”

This conversation was awkward because El, now twenty-two came out as a lesbian in high school. She could tell…they can tell.

Sara answered honestly. “No I have not, the opportunity never presented itself, and to tell you the truth I do not know what I would have done if it did. What would your father have thought?”

El just smiled and said, “I knew it, I knew it by how you looked at her.”

When we returned home El wouldn’t let it go and asked, “Mom, would you try the ‘soft side of sex’ with a woman if it were possible?”

The answer was of course simple, “It’s never going to happen, baby. No one would be interested in me that way, certainly not at my age.”

El came very close and said in a soft voice, “Mom, stop the bull shit casino siteleri excuses, I’m standing right here and I’m interested.”

El very deliberately put her face, her lips, inches from Sara’s and taunted, “Well would you?”

“El stop, I’m your mother!”

Sara never should have but she did. It was wrong but she surrendered to a long suppressed urge and with El’s lips open slightly and only an inch away Sara leaned in and initiated the first kiss.

Sara admitted her first experience with the ‘soft side of sex’ was everything she had imagined. That afternoon with her daughter was something she would always deeply regret only because she was her daughter but at the same time Sara was grateful for the door it opened.

Ron’s contribution was surprising. He offered, if his story was true, a window into himself.

REGRETS — a simple perspective.

Long before I retired and after my wife died I met a new friend, Bill while volunteering for a local charity. Bill, in his mid 60s, had also not yet retired. Bill is of course not his real name.

Bill and I talked about where we were from and all the usual new acquaintance conversation and found out we both loved football. He was also a widower so we had that in common as well. Another new person in my life, a neighbor and perhaps eventually a friend.

After talking a few times over the following weeks, Bill invited me to his home to watch a game.

I brought beer and Bill had bought chicken wings and other snacks. The pre-game show would be on shortly and as Bill left the room to get food he first turned on the TV. He had apparently left his DVD player set up from a movie because as the television came on so did the movie. Bill had been watching porn.

He hurried back to turn off the DVD player all the while apologizing. I of course let him off with a comment about how it was no big deal. I went a little overboard by bragging that I watched similar shows all the time. Just two guys, each trying to out do the other.

Bill bragged about his collection and asked if I would like to watch one before the game. Before I could answer he restarted the video. I went along not thinking much of it.

The video was of two men with a woman but it was not the two men on one woman video I expected. It was pretty clearly a couple with a guy. The men were doing much more than having sex with her. They were touching and kissing each other as well. Seeing that made me feel uneasy. Yes, I had imagined, or maybe even seen in porn, one guy sucking another but the thought of them kissing and caressing each other as lovers left me uneasy and questioning what Bill might be really like. He was sitting next to me on the couch and he was without realizing it rubbing the front of his shorts. Without looking at me he was telling me how when his wife was alive they often had threesome parties with both other men and women.

He asked if I had ever experienced a threesome. I of course told him I had not, my wife would never have gone along with that. I hinted that I might do it if the opportunity came about and I think he caught that. Now I could see that he was getting hard as he continued to touch himself thru the fabric of his shorts.

I watched as he unzipped his shorts and freed his cock. It was embarrassingly bigger than mine. He looked at my pants and saw that I was not hard or even trying to rub myself.

I just looked at him. It was not even fully erect yet but it was the longest thickest cock I had ever seen and I couldn’t stop staring.

I saw him smile as he asked if I wanted to touch it. Without waiting for a reply he took my hand and put it around his shaft. I did not resist, I did not want to resist. It was initially soft and warm to my touch but as I moved my hand it got very hard very quickly . Bill was uncut. He squeezed my hand tight and pulled the foreskin down around the glands of his almost purple cock head. I was not fully aware I was doing it unassisted but I looked at my own hand moving up and down the length. I watched as droplets formed at the slit. I was embarrassed that I was wondering what they tasted like.

I was getting hard myself but Bill was so much harder and bigger than I ever get. Suddenly his pants were gone and he was standing in front of me and he put my other hand was between his legs cupping his balls. They too were so much bigger than mine and I found I wanted to touch them, squeeze them. Bill had long soft black hair everywhere, even his scrotum was covered.

The head of his cock as only inches from my face. The droplets of pre cum were rolling off onto my arm. I heard the words almost as though they were spoken in the movie still playing on the TV, “Kiss it. You want to. Kiss it.” He had moved my hand from his cock to his ass cheek and was leaning in putting the head almost against my lips. He never did force me. In the end it was my decision, actually it just happened. I opened my mouth as wide as I could, leaned forward, and he was in my mouth. Well, the head was in my mouth. My tongue seemed to be in the way. canlı casino There was a slight smell of pee and an acid taste. I did not gag. Weren’t you supposed to gag?

He sensed I think, the panic I was feeling. He did not push himself further into my mouth but was instead stroking that part of him that was not in my mouth. There were no squirts, no spurts of hot cum. The only sign was that his knees gave way and bent slightly and he put his hand on my shoulder to steady himself. My mouth was filling and I had to swallow repeatedly to keep up with the flow of hot cum. I remember the taste was a little salty.

The football game came on, he pulled his shorts back on, and we pretended nothing unusual had just happened.

This was my first experience with another man. Did I regret it? Yes very much initially. I was embarrassed that I had submitted so willingly. Did I experience giving oral sex again? Yes, often, with him and other men.

Ron and I exchanged stories by email and without yet discussing them we made a date to talk about starting the writers group. Saturday came. I had not yet read his story and I was thinking about him as I showered. To shave or not to shave? Will he get lucky? Will I get lucky? Do I want him to get lucky? Does he want to get lucky? Was I too old? Was I too fat? Can he get it up? It amazes me how, at 63, I turn into a teenage girl at the prospect of a new sex partner.

But sadly, especially after having read his story there was no chemistry. I discovered something about myself, reading about and thinking about gay male sex was not a turn on. I had been married for years to a big hairy always horney, grabby man and it was a huge turn on when we had sex. I loved it when he patted my behind and called me babe and made me willingly submit to his lust. I had more recently experienced the ‘soft side of sex’ with another woman and that as well was a new thrill. But, honestly, Ron’s story about his first guy on guy sex left me………

I thought it would be fun to bring him flowers and perhaps a bottle of wine so I bought both. When I arrived he greeted me at the door dressed in jeans a white tee shirt and an Emeril Lagasse apron. I remember he was barefoot. I found that curious but he explained later how he was always barefoot or in stocking feet in the house.

I had on a pair of black tights. I sometimes wear them just because frankly, they complement and show off my butt. I was also wearing an oversize starched white mens dress shirt I sometimes wear because frankly it hangs low enough to minimize my big ass. I kicked my shoes off put on the apron he handed me and joined him barefoot in the kitchen.

Ron thanked me for the flowers and the wine. He told me I was the second person ever to give him flowers. He kissed me lightly on the cheek. I would later learn the first person to give him flowers was his wife on his 50th birthday. When he kissed me I put my hand on his upper arm and noticed for the first time how muscular he was. With that one touch something changed. Was it just touching him? His obvious masculinity? Was it chemistry?

As he kissed me on the cheek I touched his face and kissed him ever so gently on the lips.

We cooked, we laughed, we talked, I had a great time. In an hour or two he had become a man I seemingly had known forever. A good friend. As I looked at him across the table I saw the laugh lines of a man who had laughed often and hard. I saw the worry lines in his brow of a man who had suffered. I saw in his gray hair and beard a person who had aged into a very handsome man any woman would want. I found my mind wondering if he had gray hair everywhere? He did. Chemistry?

After dinner over wine we sat on his couch and talked. It had been a wonderful evening and I felt happy I was with him.

As we talked about our past lives I learned about his wife and how she died five years ago and I mentioned my husband and how he as well went too soon.

At the mention of my husband the conversation slowed and Ron became more serious, like he was trying to ask a question and could not find the words. I could see he was choosing his words very carefully. He wanted to ask but couldn’t. Maybe, just maybe he did not want to hear the answer. He told me he had had a great time blah blah and I stopped him.

I told him: “Look, I don’t pretend to know what you are thinking but I am not a lesbian. Like you, I am bisexual, and became aware of it after my husband died. Val and I were together here at OFH for only a year and that is probably what you heard about.” I finished, “If that does not work for you, I understand.”

I waited. He said nothing. A minute?

He took my hands and kissed me, gently but more than just a casual kiss. I don’t know why I did this but I took his hand and lead him into his bedroom. I took off his clothes and then mine and we laid in bed touching each other and kissing initially without any real intention of making love. But Ron’s erection was not to be ignored. I saw him put on a condom and I climbed up onto him and guided him into me kaçak casino with my hand. I saw he was going to cum and I reached behind, felt his balls spasm slightly and he moaned. The writers group ended before it started and friends only with Ron was a real long term option for me. We still see each other and yes we sleep together now and then.

I did not really regret my brief incest with my daughter, my time with Val here at OFH, and the one or two night flings since Val. They had shown me that I should have acted years sooner on my long suppressed need for the soft side of sex.


It would be good I think to remind you dear reader of my last interaction with Lynn. (You can read about it in more detail in OFH part 3.)

When she first approached me here at OFH it was clear that Lynn was looking for an escape. An escape from her life alone but right now an escape from her son. I could only really help her with one of those.

“Lynn, if you want you can stay here for a while. I have a guest room with its own bathroom you can use and a tooth brush for tonight. You don’t owe me anything. I have no ‘expectations.’ Tomorrow we will go together to get more of your things and visit my lawyer who can help you tell your son it’s over.”

Lynn just looked at me and said, “Do you have a tee shirt I can borrow for tonight?”

Two weeks later we were standing in the kitchen making supper and talking about where we should go from here. Lynn had just told me that she met with her son that very afternoon and the problem was solved. “Whatever your lawyer did convinced him that he needed to back off and leave me alone.” So at least I now knew the one thousand dollars I had paid him was well spent.

Lynn asked how much the legal help cost and I told her the truth. She reached into her bag, took out her checkbook and wrote a check.

I asked her, “So I guess this means you will be moving out?”

Lynn smiled a genuinely warm smile and said, “I guess I could, but who will you then cook with and laugh with late at night?”

A little confused I asked, “You want to stay? A while longer?”

Lynn took my hand and led me into the kitchen where we sat and talked as we always did in the kitchen. She mentioned that she was rather fond of how I got up late at night and made a cup of tea. I asked her how she knew that. “Tea cup in the sink in the morning and you blocking the hall light shining under my door late at night as you went to the kitchen.” She asked me if I noticed that she had been leaving her door partially open the past few nights. I had but thought nothing of it.

Then I realized what she had done and asked her, “Lynn, tell me the truth, did you know I was standing outside your door listening?”

She squeezed my hand and said, “Do you really think I always talk dirty to myself when I masturbate?” “Did you enjoy the show?” She laughed.

I looked at her and smiling said, “Why you sneaky little… You know you made me wet don’t you?”

Her eyes were smiling when she said, “I was hoping you would come in and see not just hear the show.”

In my bedroom we kissed as though we had all the time in the world. We took each other’s clothing off savoring and kissing each body part revealed. Her breasts were in fact magnificent. Perfectly round with small, maybe the size of a quarter dollar pink areola with dozens of small bumps appearing as I licked them and sucked her nipples. As my hand went down her abdomen it found light soft hair just on her mons but not a single hair on or around her labia or butt. My labia as I age is thinning and darkening somewhat. Lynn’s were still a large thick pink rose. Before the night was over my fingers and tongue explored every fold and dimension of her perfect vagina and found her pearl hidden in the folds. She moaned as I licked her lying to me by saying that no one had ever…. Lynn it seems lies a lot.

We made soft gentle love, pleasing each other with our lips and hands until early morning and fell asleep in each other’s arms.

Now back to the writers group.

I had not seen or really talked to Lynn for more than two months when I called both her and Olivia and asked them that things had changed and asked if they would like to join a women only writers group. I was honest with both of them. There was only the three of us so far. Just like that, like the Queen of OFH, I cut the men out of the group.

My thought that we could write about a subject chosen by one of us on a rotating basis and meet every few weeks. Scheduling our initial meeting was delayed because Olivia had travel plans but Lynn was was able to visit me at my home the following Monday evening.

Lynn came with stories, lots of stories, and a confession. She told me that for years she and her husband wrote stories for each other to spice up their sex life. At first it was a pretty easy way to tell each other what they wanted in their own bedroom play. She told me that over time for both of them it became much more and often involved real and fictitious other people. Then unpredictably, she wrote a story about the two of them having a threesome with her best friend Stacy. The story was one of her most extreme and involved him having anal sex with Stacy, something he often said he wanted but she said she would never allow.

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