First story! Looking forward to all feedback.
This story has elements of Femdom (both gentle and rough) including chastity, pegging, humiliation and body worship.
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I was as nervous as I'd ever been in my life as I entered the sparsely populated bar. I was meeting her for the first time and while I felt like I'd known her for years, this would be the first time we weren't communicating through a screen.
She seemed almost nonchalant when I mentioned that I would be in her home country and that I could meet her if she was open to it. It made me wonder how the meeting would go down. I didn't expect anything other than a few drinks and some casual conversation but I'd be lying if I said I wasn't hoping otherwise.
I got a few looks from the patrons at the bar. Despite the fact that I was six feet tall and had a decent body from working out, I always felt a little self conscious. I knew that it was just me overthinking and their attention was probably just drawn by the sound of the door opening but it was difficult to convince my mind of that.
I'd been thrilled at the chance to meet her. Her name was Ann, or at least that was how I knew her. We had begun to communicate through the strangest of ways. I saw her asking for people to message her over "Kik", (a messaging app) when I was looking at a BDSM themed microblogging site. She seemed intriguing even then. Most women who wanted to be messaged on that platform just liked it when men degraded them over chat or wanted to role play their fantasies. She didn't really state why she was soliciting messages from random strangers. A quick scan of her blog indicated that she was a switch. She had pictures of women being pounded till their arseholes were gaping but at the same time she had GIFs of men being kicked in the balls and fucked with large strapons. I was even more intrigued when her blog description said she was political and enjoyed interesting conversations.
With some trepidation, I messaged her a question. I mentioned that I saw her request on the BDSM site and that I was curious as to what her political leanings were. Expecting a debate she was probably a little defensive initially till she realized that I wasn't there to argue or debate but wanted to know more about her. Our discussions ranged from politics to entertainment and of course, BDSM. I was a novice in more than one sense of the word. I'd just been in a long-term vanilla relationship which was devoid of anything relating to BDSM and I was curious about everything she had to say.
Her main kinks were Femdom and cuckolding and she'd been in a few BDSM filled relationships, both as a submissive and a dominant. Her last relationship had been female led with long term male chastity. Her ex in that case was also brown and enjoyed being cuckolded, pegged and more. I've always been very cautious about my pictures being anywhere on the public domain. It was a shock to me when she sent me a picture of her face. I was immediately flustered. Partly because she was extremely attractive and partly because I felt compelled to send a picture of myself but was too nervous. I apologized, saying that I was uncomfortable with sending pictures of myself over the internet but I thought she was incredibly attractive.
She had soft looking dark hair which fell till her shoulders. Her alabaster skin had tattoos which intrigued me and she had delicate features. Her eyes though were what really drew me to her. They seemed to be warm, yet mischievous. They were the eyes which could turn most men into putty and I could see much stronger men than myself getting on their knees and submitting to those eyes.
Every time someone does something nice for me, I try to fathom what they would possibly want from me. In her case, she simply brushed off my apologies for not being able to send pictures and said that she wasn't really expecting anything in return. The way she described her old relationship was scintillating. I found myself asking questions and picturing myself in the place of her sub. We even had the same cock size (something else I found myself answering).
Eventually, when asking her what kind of pictures she sent her cuck, she sent me one of those pictures. It was beyond hot! It could have been an adorable, innocent picture. Ann was lying on her stomach and you could see her legs in the air behind her almost casually. The hottest thing though was the thick cock she was happily suckling on while she stared into the camera. We spoke about how nice the cock looked before she sent me a video of her sucking it in public. It was apparently the first cock she had sucked in public. She seemed to be extremely skilled even at that as she took it all the way to its hilt. Somehow her willingness to share made me feel empowered enough to send her a picture of myself which she said was cute.
We spoke more after that. She was intelligent and curious and very fun to talk to. It was something I genuinely enjoyed. Apart from the political talk and the memes, she was also happy to talk about her BDSM experiences and send videos of her in a threesomes and riding thick cocks while her cuck filmed.
I've always considered myself as a switch and due to being a tallish- masculine looking man, I've usually been expected to be the dominant one in bed. I do however also have a strong submissive side which had not really been let out and somehow Ann could sense this. She asked probing questions about my sexuality and how dominant/submissive I was. She mentioned that from the way I spoke to her I seemed submissive. It wasn't a conscious effort but I realised that due to her confidence and the way she spoke, it just happened naturally.
I was doing my Master's in the same city where Ann lived and when we realized we would be staying in such close proximity to each other, she said that she'd like to meet. It was interesting how she'd tell me that she wanted things super directly. She wouldn't always ask and I think that was her just pushing my submissive buttons.
I was brought back to the present when I spotted her sitting alone at a table. She was even more beautiful in real life and was casually dressed in sweatpants and a T shirt. Her hair was the same length and colour and I could spot her earrings from afar. She spotted me and beckoned me over. We could've been old friends the way the conversation flowed. We chatted about my course and the usual things people speak about before we continued our discussion about politics and life. It was in the middle of our discussion when she casually reached into her bag and put what was unmistakably a bright pink chastity cage on the table. I faltered in my critique of certain neoliberal policies in India as it caught my eye.
"Go on then? You disagree with it why?", she asked without hinting in any way at the cage on the table. Feeling my cock ironically swell and get hard, I tried to continue with my points. Midway, I felt her foot gently touch my crotch which made it far more difficult for me to continue. She watched my eyes while I tried to continue without letting her teasing show in any way. Finally as I floundered, she decided to stop playing with me and said, "Well, since you don't plan to put this on yourself, let me help you out."
I stopped speaking and looked at her quizzically. "You had enough time to go put this on but you didn't. Now I'm going to put it on for you.", she said with a glimmer in her eye and a faint smile.
With that, she got up from her chair, grabbed my hand and began to lead me to the toilet. I got a few knowing smiles and winks from people who obviously thought I was going to be a very lucky man in a very different way. Red faced, I stopped as she put the cage near the basins.
"Get your little cock out boy", she said to me in a conversational tone as I shivered at her every word.
"H..Here, Ann?" I asked, still fearful of people barging into the washroom.
"Yes. Unless you'd rather we do it at the table.", she said again in the same conversational voice.
I was floored. I unbuckled my pants and let them fall to the floor. Then I pulled down my boxers to reveal my rather average sized cock at full mast.
"Aww, so cute! You shaved as well. Such a good sub.", she said playfully as she stared at it. "Well, we don't have all day so come in now", she said, gesturing to the open stall.
Before I could move, I felt her slender fingers grip my cock and lead me to the stall. It was an electric touch and I never wanted her to let go, even as I felt her tug a little. She shut the door but didn't bother to lock up. I didn't want to risk upsetting or annoying her, not when my cock was in her hands so I kept quiet.
