Love Story between Two Old Men

We were two couples from Rio de Janeiro, good friends since college. We all got married in 1980, in our mid-twenties already with good jobs and planning to buy our own homes. Rose and Alberto were a beautiful couple. She, 5.9, 171, dark skin, black hair and eyes. He was a little taller than her, brown hair and fair complexion. Both working in the import and export company they opened, which by the way has always been very successful. My wife and I were in the healthcare field, we worked as doctors and had little time to get together with our friends.

So we always planned our vacations together. Our preference has always been the coast where Alberto and I spent a lot of time fishing and Rose and my wife Veronica took the opportunity to catch up while strolling and shopping around the city we were visiting. My wife was the petite type, 5.1, proportionate weight, red hair and blue eyes. Me 5.10, white, sunburned, 165 and silver hair because strands of gray hair started appearing on me around 17 years old. Neither of us had children and we lived primarily for each other and for work.

In general, we saw each other on vacation and always on one or the other's birthday. And so it went for many years. Until the pandemic came and took our wives, now that we were in our sixties. Deep sadness overwhelmed us for a long time until I started to react and noticed that Al, as I called him, was still wasting away and very sad. The times I visited him, I cleaned his house, made him some real food and urged him to react and get out of that lethargy. But nothing I said helped him change his mood. One day I arrived at his house "bag and baggage" and said that being his friend, I had the obligation to take care of him and get him out of that mental state before something bad happened. I said that we would take care of the house together, we would go for walks, etc. He agreed and even seemed to like the idea, which made me excited and hopeful. He said:

- Ok Rogério, I am very grateful for your concern about me and I will really try to respond to change my mind. Al took my suitcase and took me to the second floor of his large house and showed me the room I would occupy.

- You will stay in the guest room which is spacious and very comfortable. I hope you feel at home. You can use this closet to store your things. In it are still Rose's clothes, which I haven't thought about yet what to do with them. You can tidy it up so there will be room for your belongings. While you settle in, I'll make us both a strong coffee. I thanked him, dropped everything there and then went downstairs. We had breakfast and went out to the supermarket to stock the fridge and buy some cleaning supplies. When we arrived we put everything away and Al told me he had a doctor's appointment that day in the afternoon. I suggested that he take a shower and relax while I prepared a quick lunch for the two of us. I made spaghetti with sardines, which, by the way, was well praised by Al, who even told me that it turned out exactly as his wife prepared it. After lunch, I suggested that he leave the dishes to me and asked if he would like me to accompany him to the doctor, to which he replied:

- No need for Roger. While I'm going to the doctor, take the opportunity to pack your things in the closet and get some rest too. I want you to feel at home. I have beer in the fridge and spirits in the bar. Take what you want. By the way, I must take a while because after the appointment I'm going to the mall to buy a new microwave because the one in the kitchen broke. I agreed, he's gone. I cleared the table, washed the dishes and went upstairs to unpack and arrange my things. As I opened the closet, I saw dresses that I remembered Rose wearing, which saddened me a little. I started passing her pants, coats, sets, dresses, etc. to one side of the closet, thus making room for me. As I looked through the drawers, I came across her panties, bodysuits, pantyhoses, baby-dolls, etc. Being alone there, a desire to wear those clothes overwhelmed me. I used to put on my mother's panties and banlon skirt when I was young and loved the feel of that fabric on my body. So, I took a pair of black cheeky panties and a pair of light natural color pantyhose and slowly put them on, "savoring" the sensation of the contact with my skin. This wonderful sensation immediately aroused my erection. I picked up a little dress of very light fabric, which seemed to me to be from everyday life at home, and which fit me like a glove. My heart was pounding hard, making it seem as if even the neighbors could hear. In the shoe department, I picked up a pair of heeled sandals that matched the printed dress and put them on. In cylindrical boxes were wigs of various styles. I chose a brown one and clumsily put it on my head.

I looked in the mirror and thought what I saw was beautiful. Even the face with some make-up would look good. The feel of the dress on my body and the heels was sensational. I looked at myself in front of the huge mirror in the room and thought I looked really "hot".

Since it was still early and Al had said he would be late, I decided to go downstairs to prepare dinner and then change clothes. About forty minutes had passed, I was listening to music on my cell phone and humming when I felt a hand on my shoulder and Al babbling:

- What..who...are you......?

He couldn't finish his sentence and I got scared as hell. At that moment I didn't know what to do, much less what to say. Stuttering, I said I could explain everything. Al said in a deep voice:

- You were on your back just like Rose. Don't worry, I wasn't angry. It may seem strange, but finish what you were doing dressed like that.

I could only mumble:

- But.... Ãh... I....

- Be cool.... finish....then we'll talk. He said.

Very embarrassed, I finished preparing the meal and had noticed that Al was always passing by the kitchen and discreetly watching me, which strangely gave me a hint of pleasure. Without saying anything, I went upstairs to change.

A bit uncomfortable, I lingered longer than necessary in the bedroom until I went down to dinner and Al was waiting for me with a glass of red wine for each of us. He broke the ice by saying:

- All right! What's wrong? You see, your back is identical to Rose's, I couldn't stop staring at you. In fact, I'd like to see you in her clothes again, but this time let me choose.

I tried to say something that sounded reasonable:

- But.... my intention was not.... I didn't want to....

Al shhiiiied softly with his hand on my shoulder and said:

- Ro, you looked hot in those heeled sandals. I loved the image.

It was the first time anyone had ever addressed me in the feminine.

Receiving a compliment like that stirred me. Wow, myself, dressed as a woman could arouse a man's interest. From then on I began to see him with different eyes.

We had dinner and chatted when he told me:

- While you shower, I'll leave on the bed what I'd like you to wear, okay?

I said yes and went into the shower. Shaving, I decided to shave my legs as well and soon I had removed the hair from my entire body, imagining the sensation of the fabric on my smooth skin and also sure that it would please Al. After drying myself off, the first thing I did was to give my neck a subtle spray of one of the perfumes that were on the sink. On the bed was a pair of transparent black panties that looked perfect, a matching bra that was placed over a silicone bra that filled it out, an equally black knee-length nightgown that gave me goose bumps of pleasure when I put it on. For my feet, a square heeled sandal that, in spite of this, was very comfortable. To complete the outfit, a blonde wig down to my shoulders.

I went downstairs a bit shy for a chat and some TV until time to sleep. At the bottom of the stairs Al appeared and offered me his hand to help me and said:

- You look great. I've been looking forward to seeing you like this. Hmm and what a nice perfume.

We sat down on the sofa, Al put on some soft music and we sipped wine while we talked. We were very close to each other and Al put his hand on my leg and that touch was electrifying. He felt a chill run down my spine so taking courage he said:

- Rogéria, will you sleep with me tonight in my room? Your company does me so much good. I don't know what's wrong with me but you dressed like Rose and with her perfume makes me want you.

Wow, I thought I....desire myself? Me being desired by a man, in this case my long time friend, excited me a lot and I was starting to get into the "his wife" character. I could only reply softly:

- Yes Al. This is all new to me, I am enjoying taking care of you...... and these clothes

.....stop talking..... shall we go upstairs?

I noticed that Al was already showing an erection and this unveiled to me a world that I had never been in before but that amazed me and excited me a lot.

Al stood up, gave me his hand, I stood up and came face to face with him who gave me a sniff on the neck and sighed softly:

- Thank you for everything you've done for me.

And we went up to his room hand in hand. We lay down and covered each other. We looked at each other and I turned around without saying anything. Al leaned over me and whispered in my ear:

- You're so hot. And you're so smooth you drive me crazy.

And he said this touching his hard cock against my ass. I got goose bumps and pushed myself back to feel his cock better, which by this time was very hard. At that moment Al knelt down and lovingly turned me face down, lifted my nightgown, smoothed my ass over my panties and said:

- Rogéria, tonight I will make you my wife. I really want this but I don't want to force you into anything.

I replied:

- Say no more, Al. I want to be yours tonight. Just be a little patient with me because it will be my first time and I'm nervous.

I said this in a shaky, almost inaudible voice.

He then took a lubricating gel, rubbed it on my ass, which made me jump with the cold sensation that gave me goose bumps, and started to stick a finger in and said:

- That's to relax your sphincter honey. Don't be afraid.

Soon after he put the head of his cock against the little port and brushed up and down. The sensation was wonderful, but when he started pushing in, it hurt. I groaned in pain and Al said:

- Relax honey at first it hurts a little but try to push out as if you were going to evacuate that makes the penetration easier. After the little head goes in, you will feel another barrier inside. I will push harder and from then on the pain subsides and it becomes just pleasure.

I was trembling with anxiety and anticipation because I was going to be fucked for the first time. There was a mirror at the head of the bed and I would have a good view of the penetration. Al had placed a pillow under my pelvis, and pointed the head at my ass. He started to force his way in and it started to hurt. I moaned like a girl and said it hurt, but he wouldn't back off. At this point he lay down, putting all his weight on me and shoving his cock all the way up my ass. The thrill of it going in and enlarging me from the inside was wonderful. I had the impression that I had a brief orgasm somewhere inside my rectum. Al was all over my back, his cock all the way inside me, which I think was about six inches long and very thick, and he held my hands supported on the bed, without me being able to move. It was my first time, it hurt, I tried to get off to the side, moaned, asked him to stop a little, but it seemed to fill him with more horniness. He whispered in my ear:

- Shhhiii. Easy, love, hold on, I'm already all inside you, don't fight, you're my wife now. You're so tight I can't hold out much longer.

He began to pump harder, and howled with pleasure. I had never imagined feeling like a female and enjoying it so much. Al wrapped his arms under mine, pumping harder. I could see his back and forth motion over me and his face in pleasure. Kissing my neck he said:

- I'm going to cum inside you now my woman. You hottie....

And with a prolonged roar, I felt his cock swell even more inside me and spurt all his pent-up cum for so long, deep into my ass. Almost at the same moment I also came without touching my cock. Still on top of me, he said:

- There's no turning back now. You are my little woman and I will take care of you just like you take care of me.

The moment was magical, ours alone. Al got off me, pulled me into a cuddle, kissed my neck and so we slept until morning. I clasped in his arms, feeling sore but desired, deflowered and wanted.

In the morning we each took a shower in our room and I went downstairs in a short printed dress, thong panties, sandals, and a black wig, to make our coffee. When I arrived, Al greeted me with a tight hug from behind and a kiss on the lips. The sensation of his body rubbing against mine on the fabric of the dress was very pleasant. Still hugging me from behind, Al said:

- Ro, I loved everything that happened yesterday. I can't remember the last time I came with such intensity. You are so hot, your ass would make many women jealous.

When Al said that, I remembered that my wife had told me more than once that I had a woman's ass. I replied:

- Never in my wildest dreams have I seen myself being desired...desired by a man and enjoying giving him pleasure so much. And I loved it after you spilled all your pleasure inside me, when you whispered in my ear that from that moment on I was your woman and that you would take care of me.

Having said that, Al took my hand and led me to the sofa in the living room. He sat me down and stood in front of me. Without saying a word, he let his robe slide down his body and fall to the floor, becoming completely naked a few inches from me. The sight of his mature body with his semi-hard cock just inches from my face made me salivate. Wow, now I understood the meaning of one person "drooling" over another. And I was drooling over a man... my best friend who was now also my husband-lover. How complex our psyche is.... where did my masculinity go? I asked myself.

Also without saying a word, I reached forward a little and held him by the buttocks, pulled him close to me and put my face sideways against his cock. Without touching him, I rubbed my face between his legs and against his sack, inhaling deeply, feeling the man-smell he exuded, which was already arousing me. Al put his hands gently on my head and I understood what he wanted. I took his cock, smelled it from top to bottom, and sucked his glans, which made Al let out a sigh of pleasure. I licked the head and then stuffed almost all of it in my mouth. I sucked, licked, rubbed my face. Al took it out of my mouth, gave me his hand to get up, and said.

- Ro, sit on the arm of the sofa as if you were riding a horse and lean forward.

So I did. He lifted my dress, pulled down my panties, and I was left with my ass exposed. From the pocket of his robe he took the lubricating gel, licked his cock, the entrance to my ass, put the head of the cock against it and pushed slowly but firmly, holding me by the shoulders and saying:

- You are delicious. I'm loving watching my cock go in and out of your ass. You've awakened in me an attraction that I didn't know I had. I have you as my wife and I'm very happy about it.

As he said this Al was thrusting hard, now holding me by the hips and making me all soft. I felt myself filled and moaned like a woman, loving the thrusts that gave me so much pleasure.

As he came hard inside me, Al let out a delicious moan and said :- My Ro, I LOVE YOU. I want you very much, for the rest of our lives.

I answered with tears in my eyes of pleasure and happiness:

- My heart explodes with joy because I love you too.

And we exchanged a long kiss like a couple in love and went out for coffee.

The following week Al surprised me. He brought a professional to teach me the tricks of the make-up and would also teach me how to walk in high heels, sit and behave like a real lady. I had already seen a doctor and started hormone therapy. The estrogen was already starting to distribute fat around my hips, my muscle mass was decreasing, my hair was thinning, and, happily, breasts were starting to appear. Even my thoughts and feelings changed. I became more and more concerned with tidying up the house, with the care of the food, and also with setting the table with more attention to details, the extreme care of Al's clothes, etc. More confident now about going out and not looking like a caricature of a woman, we went everywhere together, including buying clothes for me. He no longer wore his late wife's clothes. I loved it when we went out to buy lingerie. Guess who picked them out? Yes, Al. He had a special appreciation for girdles because in his youth the Miss Mary ads on the back cover of some women's magazines of the time, with their beautiful and hot models, gave him countless handjobs. I love them because they keep everything in place and I feel much more feminine. Lately I have even attracted the attention of many gentlemen who look at me with discretion but with admiration, often making Al jealous.

We sold our houses and bought a nice apartment in Copacabana where we are closer to the cultural life of the city and where we always make new friends.

As a matter of fact, these friendships produced other stories that I will tell on a future occasion.

Kisses to all!