Second Time Around

Life for me was very hard after the sudden death of my wife Janice. A scumbag drunk driver had killed her on her way home from work. Thankfully we'd not had any children but even so it was a trying time for me.

Her sudden death affected me so badly that it took me over two years before I even thought about seeing someone else.

My big quandary was how I would ever find someone who could come even close to Janice. I’d been seeing a ‘shrink’ for some time and this was always the stumbling block. Even though Jan was dead, I was still in love with her. We enjoyed lots of sex games and even some quite heavy bondage at times. The big unknown was my desire to dress in women’s clothes. Jan knew about this from a very early time in or relationship. Over the years, she had gradually come to accept that it was part of who I was and then she began to even enjoy it.
She knew I had a keen eye for what would look good on her and strange as it might seem, I actually enjoyed going shopping with her. As a thank you, she sometimes bought an item of clothing for me, especially shoes. I loved wearing stockings & high heels. She liked to see me wear them as well. We often made love with both of us wearing stockings and heels. In her honour, I wore a pair of silk stockings and a corset at her funeral. Replacing her was going to be a big task.
Eventually, I got over some of the hang-ups I had acquired as a result of her death and signed up for a few on-line dating sites.
I met a few women online and got to know a few of them quite well via email and phone calls. I even met a couple and had some fun but nothing serious. I was still feeling my way in the dating game after 10 happy years with Jan.
Then one day, I got an email from Angela. Up to now, all my ‘female’ on-line friends had come about after I contacted them. I was very surprised and actually pleased to receive her email.
I looked at her profile and saw that she lived not very far from me and we appeared on the surface to be a good match. We even liked the same types of Music.
It wasn’t long before I replied to her email.
Over the next few days, we exchanged mails and I decided that I would like to take things to the next level. I gave her my phone number and invited her to call that evening.
I waited anxiously for her call that evening. I waited for a call that didn’t come.
I went to bed a bit disappointed and slightly miffed.
When I got into work the following morning and opened my email there was a message from Angela. With a fairly heavy heart, I opened it.
“Hi Alan,
I’m sorry I didn’t call last night. I was at a friend's helping her out. Her Husband has left her for a 20yr old Bimbo and needed some comforting. Can I call you tonight?
I sat back and thought about things again. Sure enough, she had not promised to call so I forgave her.
I waited on tender-hooks for Angela to call that evening. It was well after 9:00pm when the phone rang. I had to force myself not to answer on the first ring.
On the third ring, I picked it up and said, “Hello.”


“Yes. Is that Angela?”

“Yes it is. It is nice to talk to you at last. I’m sorry about last night.”

“That’s Ok. I got your message and understood you reasons. It’s good to talk to you at last.”
We talked for over an hour and agreed to speak again in a few days. That night, I went to bed that night feeling a lot happier with life in general.
The following evening, the phone rang.

“Hi Alan.”

It was Angela.
“Angela. This is an unexpected pleasure.”
“I felt that I couldn’t wait for a few days. We got on so well last night that I would like us to meet possibly tomorrow night?”

Wow! I felt… I felt the same way as well.
“Yes,” I replied, “it would be nice to meet and tomorrow is fine by me.”
We arranged to meet up a pub not far from where she lived the following evening.
I arrived a bit early for our date the following evening. I was feeling somewhat apprehensive at meeting Angela. I felt strangely attracted to her in a way that I had not felt with other women I had dated in the recent past.
She arrived dead on time and looked drop-dead gorgeous. She was tall at just under 6ft and wore at least 4in heels that made her long and shapely legs seem positively infinite in length. She wore a pretty short dress that made every man in the pub turn their head and their jaws drop wide open. The photo she’d used on the dating site didn’t doo her justice.
As she walked towards me all I could think of was “why would she be interested in me?”
“Hi Alan. Its nice to meet you at last.”

I gave her a peck on the cheek.

“It’s nice to meet you too Angela. Your picture in you profile does not do you justice,” I said smiling.
“Can I get you a drink?”

“Thank you for the compliment Alan. I’ll have a G & T if that’s Ok?”

“No problem”.

I got our drinks and we sat together. I felt like I was on my first ever date again. It was a really weird feeling.

We talked solidly for over two hours and I felt that we had got to know each other very well but there was still this question at the back of my mind that remained unanswered.
At the end of the evening, we said our goodnights in the pub car park.

“Thank you for a very nice evening” I said as I kissed her cheek.
She looked a bit disappointed.

“What’s wrong?” I asked.

“Is a peck on the cheek all I’m getting?”

“I didn’t want to seem to forthright on a first date.”

She didn’t answer with words.

Her answer was to kiss me full on the lips.
Over the next few weeks we saw each other almost every other day. We got on very well but I was still unsure about going much further. I now had two questions that still needed to be answered.
Over dinner one evening Angela surprised me with a question.

“Alan, I get the feeling that there are a few things you haven’t told me?”

She reached over the table and took my hand and said softly, “I’m not going to bite you know?”
I looked at her straight in the eyes. I could see that she was earnest in her desire to know more.

“Is it about Jan?”

I shook my head.

“Not directly but she is part of it.”

I had an idea.

“Angela, why do you always wear high heels?”

She laughed.

“Trying to change the subject eh?”
She smiled and said, “I wear them because I like to and because of the way they make me feel.”

“So do I,” I replied in a matter of fact way.

“What do you mean ‘So do I’?”

“I like wearing high heels.”

She laughed again.

“Are you a Tranny?”

“Yes. Is this a problem?”

She paused.

“It depends”

“Depends upon what?”

“On your choice of heels and other things like what you wear with them.”

“Mostly just stockings and a skirt”

“This I have got to see. Do you mind?”

“If you will answer me one question. It has been nagging me for weeks.”

She smiled.

“Is it ‘Why Me?”

I nodded.

“It is hard to say. There was something about what you wrote in your profile that said ‘Yes’. Add to that the fact that you are a widower. So many men online are just after a bit on the side. Everything about you said that you were not like this. I am also fed up with men dating women like me just to get their end away. As soon as we met, I realised that you are not like that.”

“But you could just about have any man you want. To be perfectly honest, you are bloody gorgeous.”

“Yeah but I have a brain and people expect someone like be not to have two brain cells to run together,” she replied with a huge smile on her face.

I nodded my agreement.

“I sense there is more?” I added.

“When I see you wearing heels I’ll tell you. Deal?”

I nodded.
Angela soon agreed to come round to my house for dinner a few days later.

When she arrived, she immediately looked a bit disappointed that I was still dressed as a man.
I welcomed her to my house and poured her a glass of wine.

“Did you think that I would be dressed?”

She chuckled.

“I had hoped.”

“Come on, you can choose something for me to wear” I took her hand and led her upstairs.

My cache of ‘stuff’ had its own wardrobe in the spare bedroom. I opened the door so she could see.
Her eyes went towards the collection of shoes that filled the whole floor of the wardrobe.

“You seem to have a bit of a shoe fetish don’t you my darling.”
This was the first time she had called me anything like that. My heart skipped a beat.
She inspected the clothes.
“Am I right in guessing that Jan chose at least some of these?”

“Yes why?”

“She had good taste,” she said as she pulled out what was my favourite dress.

“This is nice. Can I wear it sometime?”
“Yes… Of course you can,” my heart was pounding rapidly.

Angela pulled out another dress and handed it to me.

“I think this one would look nice on you?”

It was the dress that Jan had bought for me less than a week before she died.

A small tear rolled down my cheek.

Angela saw this, “What’s wrong,” she asked.

“Jan bought that for me just before she died. I have never worn it.”

“Oh. I’m so sorry. I didn’t know.”

“That’s ok. You don’t have to wear it if you don’t want.”

“No Angela. I’ll wear it tonight. Would you wear the other one”

She smiled and kissed me briefly.

I left Angela to change her dress in the spare bedroom.

The one she’d picked out for me was pure a silk, full-length cheongsam with a really high collar. A few tears formed in my eyes when I remembered that Jan had had it made especially for me on a business trip to Hong Kong. She’d deliberately made sure that it was very restrictive. I had not even tried it on when she showed it to me but that was waiting for our anniversary but sadly….
I was sitting at the dresser putting on my makeup when I heard the rustle of silk behind me. I swivelled around on the stool to see Angela standing there at the threshold of my bedroom.
“Come on in.”

“Are you sure? There is a lot of your wife still here.”
“Yes. Please. I know there is a lot of her. I still and will always love her you know.”
Then I looked at Angela.
“If this is going to be a problem then now is the time to say so.”
She smiled back at me.
“I know that I can never take her place but I hope that I can be different enough so that you can love me in other ways.”

I was about to reply but I stopped with my mouth wide open.

Angela came over to me and wrapped her arms around me.

“Can’t you tell that I’m really serious about you?”


“The ‘Why Me?’ question”

I nodded.

Angela then moved to sit on my lap. She spread he legs apart and sat on me at the same time wrapping her arms around me.

“Alan, you mean a lot to me. Firstly, you have not tried to get inside my knickers at the first opportunity even though I now know you would like to wear them. Then, you are so very different from every other man I have ever met. I’m willing to give ‘Us’ a real go if you are. I am sure it took a lot of effort and willpower to tell me about you and what you did with your wife. For that, I am really grateful. It means a lot. So many men keep up this impenetrable barrier that makes relationships so difficult. You are not like that. Need I go on?”

I shook my head.

“What do you call yourself when you are… Dressed?”

“Julia why?”

“Well Julia, I think you need some help with your makeup. Don’t you?”

I nodded.
Together we got dressed and ready to face the world. Well, not quite the world but to enjoy dinner together.

Angela left me alone to put on my dress. She went downstairs to look after the dinner that I had prepared earlier.

I put on the dress. I did up the zip and in doing so realised that Jan had played a little game on me. She had put a little locking clasp in the collar. I smiled to myself as I clocked the padlock home and put the key on the dresser.
I sat down again and put on my wig. This was a present from Jan for my last Birthday before she died. It was shoulder length and a dark brown in colour. I loved wearing it. She had a matching one and we had talked about going out together wearing our wigs and identical dresses.

I has to suppress some more tears as more memories of my years with Jan came flooding back into my mind.

When I’d recovered, I put on some high-heeled sandals and made my way slowly downstairs. The cut of the dress made it difficult to walk any more than a foot with each step. I smiled as I remembered what Jan had said when she showed it to me.

All I hoped was that she approved with what I was doing with my life now.
I tottered into the Kitchen to see Angela in complete charge.

“Wow Julia, you look wonderful,” she remarked when she saw me standing there.

I kissed her to show my appreciation at her comment.
Dinner was a really nice event. We were getting really close now. I hoped that she would consent to stay the night.
After dinner we cuddled together and just enjoyed each other’s company.

Suddenly and totally out of the blue, Angela asked, “Do you dream of getting a sex change?”

“You don’t hold back do you?”

“It had to be asked I suppose.”

“I suppose so. The answer is no. Yes I would like some tits but Jan and I discussed this before and she liked me insider her too much for me to get it chopped off. Is that ok?”

“Yes. The more I hear about Jan, the more I think we are alike. Do you want to fuck me?”

“If you are ready then yes I’d like too very much.”

“I’m ready but at least tonight you can’t.”

“Are you having your period?”

“Ha-Ha. Not really”

She took my hand and placed it between her legs. I felt something solid.

“That’s my little secret,” she said grinning.

“I got fed up with men trying to get inside my knickers so, I bought a chastity belt. I have been wearing it for the past three years. They keys are safely hidden at home. Do you mind?”

It was my turn to take her hand and placed it over my swollen penis.

“I can see that it turns you on then?”

“Yes it does.”
Our relationship blossomed over the next few months. We had lots of fun but I still had not got my hands on the keys to Angela’s CB. It didn’t worry me overall as we were enjoying each other’s company.

One evening, we were lying together watching some silly ‘RomCom’ when I plucked up the courage to ask her…

“Angela. Will you marry me?”

There I had said it.

I loved her and as much as I had missed Jan, I felt that I wanted to spend the rest of my life with her. Even more so, as she had accepted my ‘little habit’ so well I just felt happy being with her.
“Julia, I would be honoured to marry you but…”

Oh shit I thought, there is always a but.

“I know, this is not the most romantic of places for a proposal…”

“That’s not important but you don’t really know much about me and what I want in life.”

This really worried me. It was true that she’d been very coy about those two things.

“What do you want in life? Please tell me?”

She opened her mouth and started to say something but stopped before any sound came out.

Angela looked me square in the eyes.

“Are you sure you want to know?”

“I do. I love you and want to spend the rest of my life with you. I can’t ever forget Jan but I know that she would want me to move on. Whatever you say can’t diminish my love for you. Understand?”
The pause that followed worried me.

“I like to make love while being tied up,” she replied quietly.

“But not dominated…” she added.

My heart skipped a beat.

“Is that all?”

“What the hell do you mean, ‘Is that all?’” came her slightly angry reply.

I smiled.

“Of course I’ll make love to you while you are tied up if that is what you want.”

Then I led Angela upstairs and showed her the selection of bondage kit that Janice so enjoyed using. Seeing this just cemented our relationship. I’d truly been given a second chance and I hoped that Jan agreed with my choice.

Angela was truly my Angel of the second coming. I knew that wherever she was, Janice would approve of Angela and the second chance that I’d been given.

The End.

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