A first time for Everything Pt. 01

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Exploring beyond my experience as a heterosexual guy.
2.9k words
4.63
36k
44

Part 1 of the 5 part series

Updated 06/09/2023
Created 11/24/2019
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As luck would have it, I was visiting a relative on Cape Cod when he was suddenly called back to the city to deal with an issue at his business. As he was closing the door behind him, he told me to stay as long as I liked and to be sure to lock the door when I went out. At first, I was disappointed because I had anticipated a nice visit and time for us to catch up, but it was a quiet season of the year, and I enjoyed the thought of exploring on my own without having to deal with the summer crowds. I changed into my bike clothes and hopped on the rail trail which was only a block from his house and spent the first morning, getting acquainted with the surrounding area.

When I returned to Wellfleet, I rode into town and found a nice cafe. Had it been a hot day, I would have gone home and showered first, but I felt that it was not necessary on this particular day. Upon entering the cafe, I noticed a friendly looking gentleman sitting in the corner. He was wearing jeans and a blue oxford shirt with a light fleece. I ordered a cup of Earl Grey tea and could not resist a pastry and sat at the table next to him. As I was fixing my tea, he commended my choice of pastry. I took a bite and immediately agreed. Our conversation took off from there. We discovered that we shared a number of common interests, and I found him to be relaxed and even more friendly than I first suspected.

When I mentioned to him that I lived in a tiny house, he chuckled and suggested that I would probably find his house interesting and invited me to check it out. I think that I surprised him when I took accepted the offer.

We finished our drinks and cleared our tables and then headed down the street, a short two minute walk around the corner and down the block and then we came upon his very small house. It looked almost like a doll house, so typical for Cape Cod, dressed in its weathered shingles and decorated with flowers. Obviously, he took pride in how he maintained his little home.

We entered the house, and I was totally impressed with the look and the feel of the interior. It was like stepping back in time, but everything had its place and it was comfortable beyond imagination. He pointed out the loft where he slept and showed me the small kitchen. And then he asked if I would enjoy a second cup of tea. I gladly accepted and sat down at the table while watching him put the kettle on the stove. He sat down across from me, and we continued our conversation.

He struck me as a gentle, sensitive kind of guy, perhaps not the kind of qualities that are to be found in guys all that often, but traits which I happen to admire. Like me, he was divorced, later in life, but he had not remarried. I wondered to myself if he had an active sex life, if he was a ladies man who used his sensitivity to find his way into women's hearts, or if he had a tendency to be more interested in guys. As if he were reading my mind, he shifted the conversation to include the fact that he had not met any women on the cape. There were plenty of single women to be sure, but none of them had actually struck him has potential soulmates. I asked him if he felt lonely, and he replied that he was still looking for a good friend, that he had this silly notion that somewhere out there, there was a kindred spirit. If Anne of Green Gables could find a kindred spirit, why couldn't he? Was it possible for guys to share that same kind of friendship?

I assured him that I thought it was possible, that I had had a few friendships during my lifetime in which I felt a true bond. He asked if that included sex, and I smiled and said no, just good friendships, but then I added that I could understand how sex could play a role in a meaningful relationship between two guys. Our conversation paused, neither of us knowing just what to say next.

Breaking the silence, I asked if I could use his bathroom. He pointed, but he really did not need to. In his tiny house, it was quite obvious where everything was! I closed the door and looked around. There was a hamper with no lid in the corner, and on the top of the heap of dirty clothes was a pair of very delicate, sexy panties. I wondered if, perhaps, he had a room mate that he had yet to disclose.

I finished and washed my hands and returned to the main room. It seemed that this would be an appropriate time to thank him for his hospitality, to bid farewell, and to head back to the house for a shower, but my new friend encouraged me to sit down again. He had no agenda for the day, and he was enjoying sharing time with company. Of course, I had no agenda either, so I gladly accepted the invitation. He started by saying that he was intrigued with my comment regarding the possibility of sex being shared by two guys. I voiced the thought that two healthy , like minded guys who enjoyed sex might very well have an intense relationship, perhaps connecting in a way that might be impossible in a heterosexual relationship. He nodded in agreement.

At this point, I apologized for being somewhat nosy and asked if, indeed, a woman was in his life, having noted the pretty panties in the clothes hamper. He paused, thinking intently about his response, and then he obviously made the decision to share some intimate details. He told me that the panties were his. He stopped and studied my reaction. I was certainly surprised, and I am sure that it showed through my expression. But then I smiled and remarked that he had good taste. That seemed to break the tension that had suddenly filled the room. He chuckled and told me that he appreciated the compliment.

We talked about his interest in wearing woman's panties, something that had started early in his life. I felt compelled to share that I too had an interest and that from time to time I had borrowed a pair of my wife's panties and worn them, a wonderful secret that I found to be quite a turn on. We quickly grew comfortable talking about the eroticism associated with wearing soft feminine undergarments, and I lamented the fact that it took so much coaxing to get my wife to put something especially sexy on.

And then I asked him point blank, if he was wearing panties under his jeans. He smiled and responded that, indeed, he was It seemed like many seconds passed before he resumed the conversation and asked if I would like to see them. I sensed that once again he felt as though he had gone out on a limb. He was not sure how I would react. Would I thank him for the tea and make an excuse to quickly leave or would I accept his offer to see what was hidden underneath his jeans? I smiled and told him that I would be delighted to see them.

It was immediately apparent that he was grateful to hear that. He was glad that instead of being a conversation killer, it was confirming. Not only did I tell him that I would enjoy seeing his panties. but I was telling him that it was perfectly ok for him to share intimate thoughts, that I was interested, that I found it worth it to pursue this friendship, knowing that we might quickly open ourselves to vulnerable positions in which we shared details about our sexual fantasies. And that was ok.

It was obvious that he was pleased that I was interested in seeing his panties. He got up from his chair and slowly, but deliberately, began to unbutton his jeans and then he pulled down his zipper. He was standing just a few feet from where I was sitting. It dawned on me that I was finding this experience to be very exciting. I was intensely interested to see his choice of panties. I wondered if they would be soft and feminine and sexy, or more like the utilitarian ones that my wife typically wore. I wondered if he would be aroused, if I would see the outline of his cock through the material. I wondered how big he was. We had just met an hour ago, and here I was sitting in this fellow's small kitchen, sharing a cup of tea , and watching him undress in front of me, questions zipping through my mind.

He dropped his jeans to the floor and stepped out of them, and then he lifted his shirt tails so that I could appreciate the pair of panties that he had selected earlier in the morning. I was both thrilled and pleased to see that he had chosen a very feminine pair of panties, lilac colored and trimmed in lace, a soft, silky material.

There was no doubt that this experience had aroused him. The full outline of his hard cock was evident behind the material. In fact, it appeared that the tip was just beginning to peek out from underneath the waistband. I told him that I loved his panties, that he looked sexy in them. He took two steps closer and now stood just a few inches from where I was sitting. I asked if I could feel them. He nodded, obviously comfortable with my question. Tentatively, I reached out and felt the material, placing my hand on his hip. Of course, I wanted to be much more bold and to caress his cock through them, but I did not have the courage to do that initially. I began moving my hand on small circles, reaching farther back behind him, until soon I was cupping his ass. I told him how wonderful his panties felt.

I found that I enjoyed not only the feel of the material, but I also liked the feel of his ass in my hand. I slipped my hand beneath the material of his panties and felt the warm skin in my palm and I told him that I also liked the feel of his bare skin. He encouraged me to continue, as he inched forward just a bit, giving me complete access. He was smiling, and now his cock was straining to make it past the waistband of his panties. He had obviously showered not long before we met; I could still smell the fragrance of the soap he used, and I could feel the heat radiating from his body. His groin was inches away from my face.

He had rested his hand on my shoulder, and he was massaging it.

Immediately, I felt a little self-conscious. Here he was freshly showered, and I was still sweaty from my bike ride. But I let that thought pass as I reached with my other hand to caress his cock through the fabric of his panties, asking if it was ok with him. He smiled.

The contrast of the soft feminine panties against the hardness of his cock struck me as highly erotic. I reached around him with both hands and slid them under his panties and gently drew him towards me, and then I laid my face against his panties, feeling his cock against my cheek, inhaling his fragrance and getting totally lost in the eroticism of the moment. It seemed completely natural then to turn and to lick the underside of his penis through this panties. I wanted to see it, but I wanted to continue to enjoy the panties as well.

I made them wet with my kisses, and then I felt the intense urge to have his cock inside my mouth. I reached for the waistband with both hands and gently slid his panties down, revealing first his cock and then his balls. The panties dropped to the floor and he stepped out of them and then put his hands on my head, pleading without words for me to resume.

His cock stood at full attention, just inches from my face. For a brief second it dawned on me that I had fantasized about this very situation so often, but now, here I was, faced with an opportunity to fulfill that fantasy with a new friend who obviously longed for the same thing. I once again focused on the present as I reached out to touch his cock for the first time, lightly grasping it with my hand, feeling the hardness but noting the soft, smooth skin, especially at the tip. A drop of pre cum was becoming evident at the tip just before I guided it to my lips and softly kissed it.

I tasted his pre cum and took time to appreciate the erotic sensation of feeling his hole with the tip of my tongue. I breathed deeply, again enjoying his fresh fragrance and then I became aware of his hand on my head, gently urging me onward. Slowly I enveloped the head of his cock with my mouth, being content to simply let it rest as I explored it with my tongue and then ever so slowly sliding more of it in my mouth, feeling it hit the back of my throat and then stopping. I had read that it took a while to get used to the feel of a cock in one's mouth, and I was not about to rush the experience in any way.

I dropped my hand and turned it upwards to cup his balls, so warm and soft and full. My fingers extended to the area where his scrotum disappeared, that soft, sensitive spot just before his rosebud, and I massaged it. I could tell that he enjoyed what I was doing because he moved his legs apart, making my access that much easier, not to mention hearing him utter the word yes, holding the s sound for seconds before allowing it to trail off into silence.

As I continued to massage his balls, I concentrated on taking more of his cock in my mouth, sliding back and forth and each time trying to open the back of my throat so that I could accommodate him. It took me by surprise when I began to feel his body tighten. At the same time he began to let out a low moan, and I then felt both of his hands on my head. He did not thrust, but, instead he was very gentle. It was clear that he was on the brink of an orgasm, and then he addressed me. He did not use my name, instead, he called me lover, and his cock began to pulse. I could feel the movement in his balls. Soon I was experiencing the warmth of his cum as he spurted inside my mouth. He continued to moan, his eyes closed, the look on his face that was a cross between sheer agony and total delight. His cock slipped out of my mouth but his cum continued to spurt out against my cheek, hot and wet.

As his orgasm subsided, I rubbed his penis with his cum. It was still hard and now it was slippery, a wonderful sensation. Helping my new friend to experience such intense pleasure led to a feeling of great satisfaction. I have always been one who enjoyed pleasing others, and I had just experienced the intimate pleasure of pleasing a friend. The whole adventure was one of intense intimacy. He clearly felt comfortable with taking the step to share his love of wearing panties, exposing his vulnerability, exposing his body., and allowing himself to sink into the depths of an intense orgasm in the presence of someone whom he barely knew.

I had read that many guys meet in adult book stores for just this type of experience, barely communicating, and then leaving the establishment seconds after ejaculating. One taking pleasure in an orgasm and the other simply being satisfied with sucking him off. Was that how this experience would end? I barely knew this guy.

Did he expect me to excuse myself, visit the bathroom and splash some water on my face and then say thanks, and head out the door? Or did he intend to continue the discussion? When I stood up and looked into his eyes, I noted appreciation, the kind of deep appreciation that a true friend would feel. He told me that he was unsure if he had ever cum so fast and hard in his life, and he described the experience as beautiful with more intensity than he could ever have imagined. Then he told me that he hoped that I was not in a hurry and that I would agree to stay for a while, suggesting that we had more to discuss. That was the answer to my question. He surely wanted me to stay.

But if there was any room for doubt, he then took a step towards me, reached out for the hem of my t shirt and said that he could not wait to see me naked. I wanted him to undress me, but I expressed my concern that I had ridden 30 miles in the warm sun and was still sweaty. His response was that we could begin with a shower together. I smiled and followed him into the bathroom.


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15 Comments
AnonymousAnonymousover 3 years ago
Beautiful Story

Your story itself made me feel comfortable, and calm, and wishing I had been the one you met at the cafe. Good, evocative writing!

AnonymousAnonymousover 4 years ago
Loved it

I really liked the story ,can never find someone like the older guy in the story

AnonymousAnonymousover 4 years ago
Beautiful story

Have not previously read this story, logged on this morning and saw part 2. Interested in the title, I decided to read part 1. Wow! This is a very beautifully written story! I can’t wait to read part 2! I guess a lot of us can relate to how the story unfolds and can place ourselves in this situation. Living and growing up in Texas, it would be hard to find a friend like this. But one can dream!! Thank you for sharing your writing talents!

AnonymousAnonymousover 4 years ago
Ah Wellfleet

I’ve been to that Wellfleet Cafe a variety of times when my wife was away. If only I was a bit more aware of my latent desire. I might have been able to meet one of these men, if not both.

AnonymousAnonymousover 4 years ago
This is beautiful.

This is a wonderful beginning to a very promising story. No humiliation or degradation. Just two mature, divorced men exploring their long held gay fantasies with each other in a mutually respectful and satisfying way. I'm hoping their relationship becomes deeply emotional as well, which to me is incredibly sexy. Gay men passionately sucking and fucking is lovely, but even more so when the guys involved fall deeply in love. That's the ultimate homoerotic turn on for me.

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