Silk Stockings

ADVISORY: Some of the content in this post is suitable for adults only.

When I saw the prompt for 4 THOUGHTS or fiction was stockings my mind jumped to Greg. He was the first man I had sexual contact with after I broke up with my first boyfriend (a ten year relationship that lasted into my mid-late twenties). Looking back, I guess my first boyfriend treated me like a young girl. That was fine. After all, we were teenagers when we met and developed a close friendship that resulted in us becoming sweethearts.

After we broke up, I just did not know who I was ever going to imagine myself being with. It was excruciating for me for some time. I dated half of the guys in the city I was working in at the time. I moved, partly believing a change would do me good and partly because I had an amazing job offer and started to earn a lot more than I had before. I felt very downhearted though. I was desperately lonely. I was going though the motions without any real direction.

It was then when I crossed paths with “Greg”. I had first met him when I was very much a child. He knew my parents. He was kind and charming. At first, he invited me out for a drink a couple of times, took me for dinner, took me to the theatre. He acted like a family friend offering me some support and encouragement. We kept in touch – a lot. He kept asking how I was doing and we would talk on the phone and send emails to each other regularly. I shared everything with him. I told him about the breakdown in communication with my parents. I told him about why I had broken up with my first boyfriend. I told him I was lonely and lost. He told me he felt lonely. He told me I was his best friend.

Then something changed. I still have his emails so if I wanted to I could go back and figure out when and how it changed, but I don’t really want to relive the shift in the way I felt about Greg. All I knew is that gradually our emails became erotic. Greg began to fantasize about what he wanted to do to me. I enjoyed his explicit imagination and responded eagerly.

Can you guess what happened?

I don’t want to write about it in detail, but the short story is, I found myself in bed with him. Greg was a man who loved erotica. He was a stark contrast to my first boyfriend. He had already moulded me in some ways so when we were alone for the first time, I was wearing the kind of dress he had instructed me to and the kind of lingerie he wanted me to wear. It was all very sensual, highly erotic. He wanted to breathe in the scent of me. I remember him issuing orders, “Lift up your skirt for me,” as he knelt down and pressed his nose against my panties. He pulled them down to my ankles and asked me to part my legs. His hands ran up my thighs and he kissed the front of my woman hood before his tongue began to probe my pussy.

But the main reason Greg wanted me was my breasts. He loved large breasts. He had frequently mentioned his desire to suckle from me for extended sessions. So, the main feature of our relationship was exactly that.

While Greg and I were meeting up for him to have me dress up for him and dance erotically, and then for him to tease my nipples and suckle from them until he was satisfied, he did not want to take me out anywhere on a date. He asked me not to tell my parents or any of our mutual friends about our relationship. I was kinda disgruntled about that. To pacify me, Greg gifted me. He was a wealthy man, and I was overwhelmed by some of what he gave me. In fact, I flatly turned down some of his gifts. I remember becoming deeply offended and telling him I was not his whore.

However, there was one gift that I accepted and felt flattered by. Greg bought me stockings, beautiful silk stockings. He had often mentioned that he wanted me to wear stockings when we met together. I wore pantyhose or in England we call them tights. I was still so girlish and did not realize that pantyhose were not sexy. I remember eagerly donning the first pair of stockings he gave me and buying myself a suspender belt to add something else to the erotic lingerie I was dressing up in for him.

Greg transformed me in some ways from a girl into a woman. He made me feel incredibly sexy and desirable. Only he also caused me to feel disgruntled and insulted. I never will understand why I had to be his dirty little secret. I never will understand why he had so little interest in intercourse, which was something I craved. I still feel sickened that he thought gifts could keep me malleable.

Some of my close friends found out later that Greg had been intimate with me. I was surprised by their reaction. Most of them were mad at Greg. It is complicated. I think it is still a raw nerve with them to this day that a man so much older than me (I guess he was old enough to be my father, but that is not unheard of) had an illicit affair with me without dignifying me by taking me on dates in public. I think that because he is wealthy and he swans around in sports cars and designer clothes and is always travelling overseas (not so much in 2020), people resent him a little anyway. But when our friends realized that he had coached me into agreeing to secret liaisons rather than making it known we were involved, well, it has lowered their opinion of Greg. I don’t think Greg cares.

He still emails and calls me occasionally. He did so all the time I was with Simon. Ben is not comfortable with some of the content in the emails that Greg sends. It is more than just the content. Ben has a very low opinion of Greg for treating me effectively like his private sex doll and trying to gift me to keep me cooperative. So when Greg sends an email to me now and he claims to be missing by beautiful breasts and sweet nipples and wishing he could see me to suckle from me again, it really makes Ben angry. Ben has my email account linked to his phone so he can read any emails whenever he wishes to (a decision we made together).

It is a sticky situation. At the time, I adored Greg, I believed I was in love, which is why I was thrilled to be allowing Greg to enjoy my body. I still possess several pairs of the silk stockings he gifted me with. Greg helped me to see that I was not just a girl, I was a woman, a woman with a beautiful body that inspired erotic fantasies. I have mixed feelings about him. In some ways I am glad he helped me to discover my sensuality. Everything he did to my body was pure pleasure. Yet, in some ways when I think of how he treated me, I feel degraded. It is complicated. I try not to let myself become imbittered. At the time I was with him, there was nobody else in the world as special to me as Greg was.

If I close my eyes to the reality, I imagine the smooth, silken feelings and sexiness. But my relationship with Greg is as prone to damage as those silk stockings. Many times I have felt shame and pain over the nature of our relationship. In some ways, I think he abused my trust and took advantage of me at a time I was lonely and vulnerable. But I was an adult. He did nothing wrong in the legal sense.

Still, when Ben was away earlier this year, and Greg sent me a series of emails begging me to agree to meet him so he could suckle from my breasts, I became so distressed I drank a hell of a lot of wine, not knowing how to make it clear to Greg that me made me sick.

I want to keep Greg firmly in my past. I can romanticize what happened so long as it is all behind me and all sparks extinguished. But I don’t want to end our contact completely. I want to keep him just as much as I want to keep the silk stockings in my underwear drawer. Maybe Greg did not realize it fully, but I was as delicate as the silk stockings he bought for me. He did not know what he was doing, but he ruined me. I plummeted to the deepest depression I have ever experienced. My friends had to patch me up again.

Woah….I had no idea how much I would have to say on the subject of stockings!

14 replies on “Silk Stockings”

Thank you Cliff.
I didn’t expect to write so much. I started off thinking about sexy I felt when he first gifted me with stockings and I put them on for him.
But when I look back at that stage on my life – it was not right – for so many reasons it was not right. I suffered a lot because it was so not right. I just did not see the reality of the situation at the time.

Now I am in a relationship that is so right, so beautifully right, it is healing and rejuvenating, energising and has brought so much joy and peace. Ben is in a league of his own. I am deeply grateful he found me.

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love to hear about your true tales of he past and Greg was something that you needed to go thru I expect. Many things about him made me smile. In hindsight i can see what guys like him are all about. But it is important you learned by your relationship with him and remember you allowed it.
And – yes – silk stockings are the best.
PS. I am not keen on anyone having my email password. Privacy is important IMO. But I learned that the hard way…
May x

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I understand the need for privacy. Maybe we came to that agreement because of our extended periods of separation. Ben travels a lot for work. Having access to each others was more a symbol of mutual trust. I don’t think either of us have time to check each other’s inbox, but either one of us could if we felt anxious.
Sometimes I will curl up with Ben when I am writing an email. I get some pretty flirty comments and emails since I started writing this blog and I like to make sure Ben is with me so he can supervise the communication I am having with strangers – I make it clear to them also that Ben is aware of the messages between us.
I just feel so much safer and happier and at peace with that.
Ben is in no way controlling. But I never want anything to ruin what we have.

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Greg thinks he makes his own rules – I was swept off my feet by him back then. I have my regrets about that since. His emails are inappropriate and sometimes I am too soft with him because I do not like to be horrid to someone who I was so close to. But I have learnt to ignore them and send occasional short messages to him saying I hope he is well etc. Just throwing lots of cold water on him without being horrible seems to be the key. He is a long time family friend and business associate of many of my other friends, so he will always be on the periphery of my universe – but I have made clear we are history.


Wow! I am really touched.
You know May, when I started writing that post, I had no idea what was going to come out – sometimes writing these personal posts is very good for me – it helps me to process the past.

I am still fond of Greg, however, I know it was not really right. It may have been all legal, but it was not right. It’s easy to say that in hindsight, and at the time I truly thought I was in love with him, and I would have married him if he had asked me. But that’s the last thing he was going to ask me. I only realized later that I was part of the lifestyle Greg likes to enjoy, and can generally afford to enjoy. I just hated that he essentially viewed me as a commodity and although I have no doubt he was and still is fond of me, he saw me as a toy. When I was depressed, he showed no concern. For me that is the biggest gripe I have with him – he was not concerned with my mental and emotional health. But our friends have a different kind of gripe with him and although he is so wealthy he perhaps does not really care, but when news spread of our relationship a lot of our friends were outraged.

Yet….I cannot cut him off. For a while, he meant the world to me, and I prefer to keep the memories in rose tinted locked case than try to rid myself of them. I don’t want to hate someone I loved – but neither can I love him. I am just fond of him, so long as he keeps well away from me.

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