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Are You Trying Turning Me Into A Sissy -
🕑 Added 2024-03-28 14:42:31 +0000 UTCChapter 3: Things go a bit further.
My contract to install computer software for a small construction company was coming to an end. There was still some work at remote sites, but the office-based work was completed. I hoped that I would get some further work for the same company, but that would be a few months away. I had taken on a number of new hairdressing and beauty salon clients to look after their accounts.
I had some good news about the game that I had developed, which had generated some additional and unexpected income. After a long discussion, Victoria, who had been given a small promotion, and I decided that when the contract work was over, I would use the extra money to invest because I could devote a small amount of time to it each day.
Our sexual lives had continued at a high level, maybe not every day but six days a week and occasionally a couple of times a day at weekends. We were in absolutely in love.
One cold morning that autumn, I was pulling on a pair of black silk briefs that were my favorites when Victoria asked me what I was doing that day. I said, "I have to visit two building sites to reconfigure their IT systems. They are in porta-cabins, and I will be bloody freezing all day."
"Too bad you don't wear tights; they would keep you warm," said Victoria. That shook me, and as I looked up, I saw that it had shaken her too. After 10 seconds of inaction, she reached into a drawer and handed me a brand new pair of 60-denier opaque black tights. She said nothing, and neither did I.
I hesitated for a moment and then took the offered packet. I was greatly pleased that Victoria stepped out of the bedroom at that moment. I sat on the bed, and having watched my wife do this many times, I pulled the tights over my legs and set them snug about my waist. For just a moment, I relished the feel of the fabric on my legs. Wow!
Then I pulled on socks and trousers. When I got downstairs, Victoria ran her hands over my butt. "Mmm" was all she said. My trousers had more room than normal. As I slipped my shoes on Victoria, I observed.
"Socks as well, I see."
"Yes, I may have to slip on wellies, and there is a limit, you know."
"Of course, dear, and none of my heels would fit you anyway."
What was that about? Wearing pants had become something I accepted, even if I still felt it was a little odd for a guy. A pair of tights was just for some warmth on a cold day, wasn't it?
We got home at about the same time and sat together in the kitchen, waiting for the oven to heat up.
"How was your day?" she asked.
"You were right. The tights kept me warm all day. They feel good. I was aware of them, and I thought it was erotic."
She handed me a bag. I suddenly knew what was inside. Half a dozen pairs of tights of different deniers, all black, and a pair of 'hold up' stockings.
"What is this?"
"I thought that you would like them.
I decided to get some different thicknesses to see what you preferred..
"All black?"
"Yes. You could use some without socks and not be too noticeable."
She answered, "Without socks? I doubt that, and as for being noticeable,.
No nude or tan ones?"
"We can do that if you like, but perhaps you should decide on denier first, and then we can experiment with colors. Perhaps even a pair of 15-denier nude glossy ones eventually.
"The day you get me wearing a pair like that with heels, you can call me a sissy, and I won't complain."
"But you will be my sister, and I will still love you." Later that night, we went to bed, and Victoria persuaded me to keep the tights on.
Then she came after me with a pair of scissors.
I was petrified, but she calmed me and cut a slit in the front of the tights and the pants (my favorites!) to release my throbbing erection.
Sex was better than ever. It was harder and lasted longer.
Victoria was so turned on; she came so many times that we lost count.
The next morning I was out at sites again and pulled on a new pair of tights, 80 denier this time, and decided that they were thick enough that I left off the socks.
Victoria did not realize that until the evening.
"My god, I'm so proud of you. You are my hero and comfortable in yourself."
"I'm not sure about that. It is exciting, I don't deny it, but it is scary, and I have no idea how I will feel if someone else notices. The humiliation may kill me!"
"It won't kill you, and I will always be here for you. Remember that I love you."
That night, the sex was a repeat of the previous evening.
"We need to find another way to do this, or we will go broke with a new pair of tights each day," I pointed out.
"Maybe you should try the hold-ups, or I could get you a suspender belt."
"Hey, a suspender belt may be too far."
I went quiet for a while.
"How far is this going to go?"
I asked. "I don't know my love. I love this, and I think that you do too, but if you let go, you might enjoy it more.
We aren't hurting anyone."
The following morning, I was getting ready when Victoria asked if I was working outside again.
"Not today. I'm at the salon today."
She handed me a packet of 15-denier black tights. I looked stunned and was about to protest, but thought better of it. As I pulled them on, I realized that this was a feeling that I would want to repeat.
As I traveled to work, it occurred to me that I may actually have to accept the title of sissy one day. For some reason, it bothered me less than I expected. Little did I know, that day was closer than I thought.
Dinner was underway, and I was halfway through my first glass of wine when Victoria arrived home.
"How was your day?"
"Great, I got a lot done. I got away sharp and got dinner underway."
"I had a good day too. Have you changed?"
I knew what she was referring to.
"I am still wearing the tights. I knew that I was wearing them all day, and to be honest, I was enjoying them. I suspect that they may not last until tomorrow."
"Do you recall the conversation that we had last night about how you would feel if someone found out about what you were wearing?"
I paled; I remembered the conversation, and suddenly I suspected that the time had come.
"Julie called me today. After speaking to her, you talked to her apprentice, Jess."
"Yes, she made me coffee and was asking me about something on the IT system. She's a lovely young lady, about 18; she's quite attractive. What about her?" " Well, apparently, Jess has a fancy for you.
It's okay. I know that you have never done anything to encourage her; Julie told me that. Jess thinks you are really nice to her and everyone else and treat her like you are her older brother.
After you had left, she asked Julie if she knew why you were wearing tights."
Well, I went white, my head swam, and I slumped. Oh, Lord, I was busted. I was so embarrassed; I was ruined.
"It's okay. I told Julie that we were playing. I told her a bit about it and also that it was the first time that you had worn tights today. She had no reason not to believe me."
"What did she say? "She thought that it was great for you to be so secure in yourself that you would do that. Jess, apparently, thought it was so sexy."
"But I have never done anything; I would never do that; I had no idea."
"I know, darling, but you have a fan; they know, the world has not ended, you have not been arrested; they know, and they don't care."
I was quiet for the rest of the evening. We had great sex again.
I did not wear tights for the next two days.
But I have to admit that I sort of missed them—the way they enclosed you, the feel against your skin. The sexiness. What did I just say to myself? Saturday started out like any other weekend day. Papers, chores, and a bit of shopping.
That evening, Victoria and I were due to go to a dinner dance organized by her company. It was part of a celebration, and thank you to the staff. It was a dress-up formal affair, dinner, and a bit of dancing, due to finish at midnight. Victoria had been sorting out her outfit for a couple of weeks.
She was going to wear a stunning long halter neck dress that showed lots of cleavage, a pinched waist, and a slit up one side of the skirt showing lots of leg. That was paired with a stunning pair of heels that made her tower over me.
Sexy, oh yes. Late that afternoon, she brought me a coffee and said that she wanted to talk.
"I have a request. I want you to hear me out before you say anything. We have had some fun over the last few months with you wearing female underwear.
It has led to great sex, and I admire you so much."
I interrupted, "Where is this going? I'm worried."
"Please hear me out."
I love you, adore you, and you are wonderful. I am very lucky, but I have a request.
Tonight we are going to be dressed up, with a sexy dress and you in a smart, sexy tux.
My dress is split so high that I have to wear tights, but they will be glossy and sexy.
Would you wear some stockings, with a suspender belt, under your tux?"
I did not know what to say.
I was lost for words. She waited, and I waited.
"Yes, for you, I'll do it."
She was so pleased and excited that I was delighted that I had said yes. I had no fears. Half an hour later, she clipped the suspender belt around my waist. She handed me a pair of opaque stockings, but when they were on, despite them feeling incredible, we both knew that was not right. We tried a pair of 15 deniers, and they felt so much better.
A pair of new black French knickers that she must have bought recently, and in my size, were next. I had an erection, and I felt sexy. I know that sounds so wrong, but something was wrong. Victoria frowned and was deep in thought. "What?" I asked. "I know what it is, but you are not going to like it."
I loved her. What could she suggest? I had agreed to wear stockings and a suspender belt, and I was a guy.
"Your legs look good, but they are too hairy. I'd like you to shave them."
"What? Do you want me to shave my legs?
What would people say if they knew?
Are you crazy?"
"Yes, I want you to shave them; actually, hair removal cream would be easier. Who is going to know? In any case, Julie and Jess know you have been wearing tights. And, no, I'm not crazy."
I thought about it for about 30 seconds.
The feel of the tights on my legs might be incredible with shaved legs.
"Okay, I'll do it." Victoria whooped with delight and hugged me. She added, "I'll shave too."
"You already do."
"No, you once said you wanted me to shave my pubic hair.
I'll do it today."
Wow, that had been something I had asked her to do a long time ago, but she refused, and I loved her, so I accepted it.
"Why?"
"You are doing things to me; that seems like a small thing to do for you." Half an hour later, we were getting dressed.
Victoria had pulled on a pair of high-gloss, very sheer black tights without first putting on knickers. The sight of her naked pubic area through the hosiery was very sexy.
After putting on her dress, she stepped into a pair of black heels that were at least 5 inches long and so bloody and sexy that I had an erection. Her makeup was perfect, and I was fascinated by watching her.
I pulled the suspender belt and stockings on again. The feeling as they covered my shaven legs was so good. I have to admit that I love this feeling, even though I still felt that it was a bit odd for a guy.
The black pants went on, and I dressed in my tux, bow tie, and dress shoes. The trousers were long enough that I felt I could get away without socks. I was getting more adventurous! We looked great together.
The dinner was good. We chatted with some of Victoria's work colleagues and danced a lot. Very close, very loving, and very sexy. No one spotted anything amiss, but I was aware of my underwear, and so was Victoria. It was a fairly early finish, and we were home just after midnight. Victoria released the halter of her dress just inside the door.
"You like?" The sight was stunning. She stepped forward, removed my jacket, tie, and shirt, and released the belt of my trousers. They fell to the floor, and I stepped out of my shoes. We headed for the bedroom and fell onto the bed. We spent some time kissing, stroking, and touching each other. Victoria paused and lifted up onto one elbow.
We went at it for some time, and both climaxed loudly exhausted. After a few minutes, Victoria said, "Wow. That was something else. The feeling of our legs in hosiery together was amazing.
Did you feel it too?" "Yes, I did; I loved it."
I know that I have said it seems wrong for a guy, but the sensations from wearing them and that experience make me think it must be okay. I did love it.
She came several times before collapsing.
At first, I thought that she had passed out, but she was just wiped out. After a few minutes, she said that she was thirsty. So was I. I left the bed to go and get a drink.
Before I left the bedroom, I slipped on the robe that had been over the back of the dressing table chair. It was the robe that matched Victoria's long-night dress. I have no idea why I did it. It just felt right, and I suppose that in part it covered the stockings and pants that I was still wearing.
When I returned to the bedroom a few minutes later with a bottle of cold water from the fridge, Victoria was up on her elbow and saw what I was wearing. "Very sexy. Come back to bed."
I think that the sight of what I was wearing aroused her, but I can't be sure. I know that I was aroused again.
Eventually, we fell asleep. About 10.30am, I woke and found the bed empty.
I heard Victoria downstairs, so I headed to the shower. A few minutes later, I heard Victoria in the bedroom. "I'm just popping out for some croissants and the papers. I've left some clothes for you. See you soon."
Ten minutes later, I emerged from the bathroom and stopped dead. On the bed was the suspender belt I had just taken off (but it was the only one we, I, had), a new pair of glossy black stockings, a clean pair of black French knickers, and the robe.
I had worn a long night dress earlier that matched it. Wow, I thought. What we had experienced in the last few months had been incredible and was something I would never have believed I would be involved in. I pulled the clothes on.
I felt those sensations again as I pulled the hose up. The night dress fitted, but it was tight, probably a size too small, but the sensation as it touched my body was, well, amazing.
I checked myself in the long mirror, and I could not believe what I was doing.
Just as I was about to turn away, I noticed that some chest hair was visible above the top of the nightdress. It looked wrong, and without any thought, I took my razor and cut away the small amount of hair that was visible. There wasn't much; I wasn't very hairy anyway, but it looked better.
Victoria was back and pouring coffee as I walked downstairs. She looked up, took in the clothes, and smiled. Actually, it wasn't really a smile; it was something else—lewd, approving. I was not sure, but I realized that she wasn't angry or disappointed, and I knew that I loved her.
We had breakfast and read the papers without any reference to what I was wearing or what had taken place during the night. Two hours later, Victoria looked up.
I can only describe the look on her face as disgusting and lewd.
"I'm Randy; come and fuck me." She got up and headed upstairs. I followed thirty seconds behind her.
When we reached the bedroom, she pulled her sweatshirt off—no bra, I noted. She dropped her jeans, and my jaw dropped. She was still wearing the tights she had on the previous evening and all night. There was the slit, and there was dried cumin.
She looked over her shoulder and said, "I just fixed my makeup when I got up. Would you like me to shower?"
I shook my head. "Good answer.
That is what I did.
The last few weeks have been amazing; last night and today are incredible. You cleaning me up is so erotic, but you don't have to."
"I know, but if you like it, I like it. Your own cum eater." "What? My own cum eater? You dirty bastard."
She laughed, then stopped.
"That nightie is a bit tight for you; perhaps I'll treat you to your own." She flicked the lace at the top of the chest and noticed the hair.
"Did you shave that?"
"Yes, just the bit that was visible, it looked wrong." "You have come a long way."
A few minutes later, "Maybe you should shave the rest. The feeling of having clean hair is amazing for both of us."
"I'm not sure about that," I replied.
"Why not? Who's going to know?"
"No one, I suppose."
And after a brief pause, "Will you do it for me?"
"Oh yes, with pleasure, yours and mine, I expect."
She was right.
After shaving my chest and underarms, she rubbed body lotion until she got to the pube.
"Perhaps we should trim these a little."
She reached for the hair trimmer and took away at least two-thirds of the length. My hard-on was as stiff as possible.
"My god, that is so erotic."
"Imagine how it would feel if I got rid of it all. We would match." And she tittered.
"Go for it.
We've come this far."
"Really?"
"Won't it be itchy growing back?"
"Only if you let it."
And laughed before reaching for the shaving cream and razor. We went back to bed and had sex again.
It was a repeat of earlier. Great.
The feeling of being free from hair was interesting; at least that was how I felt about the body and leg hair.
I would not want to describe how I felt about the pubic hair, but I knew that I would not have to worry about stubble! In the early evening, we had showered together, although nothing happened as we were too exhausted, and dressed casually.
Yes, I was wearing pants, but I'm not sure where my men's underwear was. Over a glass of wine, Victoria spoke, "That has been an amazing few weeks, and the weekend was something else. I love this experience and adore you. I have no idea where this is going.
I took a few minutes to consider my response.
"I have loved it and love you with all my heart. None of what we have done these last few weeks has been my idea.
It has all been your suggestions, and I have gone along with them, even though I have had doubts and resisted parts from time to time. I have enjoyed it, and I hope that we can carry on, but you will be the instigator. I hope that you push a little at a time, but I can always stop, can't I?"
"Of course, my darling. I will instigate; I may put you in uncomfortable situations, and I will push, but you can say no."
Soon after that, we went to bed and fell asleep, exhausted by our activities.
Comments
Lorena Sophia Delpino
Enjoying the story brings back memories of another time from the past where my first wife and i enjoyed the beginning of what was to be.
Natasha
Love this slow build up of enjoying the wearing of girls clothes and the feminine feeling they give . She is going to adore her first bra and still can look forward to dresses and heels
J Chimera
And further and further down the rabbit hole they go! Incredible and exciting story.
Urban
Thank you for informing me.
J Chimera
There seems to be a problem with the links for this story. Clicking on Part 2 takes you to Part 3 instead.
Brianna Demonet
I'm loving this story
Sallymarie
As Amanda has said Enjoying this story
Amanda
Enjoying this story. Interested to see where this leads.❤️😂💁♀️
