A Date With My Coworker

Well I sat in the car very relaxed as Troy drove us to town , after all he was a workmate.

But they each had a secret. From Lisa’s point of view, Troy had actually asked her out over a month ago and not two weeks as she told John. He had mentioned cuckold and sissy cuckold that part was right. But before she eventually accepted his invitation she had spent hours at work looking up sissy cuckold and that’s when she got the excitement to make John into a sissy as she found from reading all the stories if she wanted to go out with Troy first she had to make John a sissy and female.

But first she had never wanted to go out with Troy, but it was after reading the stories of interracial dating and sex that she got excited for him and masturbated, but she had to guide her husband John to be what she knew he was

She also spent time reading about black men and what it was like to date them and how a girl had to be careful as it was easy to fall for their black cock and how they likes shaven pussy just like John wanted her to do for years.

How most black men were great lovers But be careful as once a women goes black she may not want to go back to white cock, especially if it’s a smaller white cock. So Lisa read all about black men as lovers and many black sex stories, she was hooked and it was a challenge to her not realising she was playing with fire.



Now Troy had a secret too, after Lisa went home Troy used to check her history on her work computer everything she had been reading, mostly about cuckolding sissy husbands interracial sex... He knew she knew she was taking a risk going with him on a date but she seemed to wanted the excitement.

Judging from her progress on line with making John a sissy, he thought that John was by now a sissy and he would soon make him a sissy cuckold.

So Troy was a step ahead of Lisa and knew she was a risk taker, he knew he would have her sitting on his cock as she had most likely made John a fully fledged sissy.

As she seemed to spend a lot of time looking up the advancement of making your husband a sissy so he must be by now.

Troy was ready to own Lisa, but his still had to take his time and not frighten her. The chase and conquest were the challenge ahead...she was reading more and more about black sex a lot of stories.

The Date.........

As they drove to town Troy asked was there any problem with her husband John was he ok about going on a date with a coloured man. No Troy that’s silly we are not racist coloured or otherwise.

Lisa I hope you don’t me mind saying but in meeting your husband he appeared to look lovely, even pretty very female even sissy. Oh Troy you are quite observant actually yes my husband is quite a sissy but I love him very much, it is nice as he is quite passive , pretty yes and so nice to live with. We are a very happy couple.

Well that’s nice to have a sissy husband, usually in the case of a sissy cuckold husband it is much more acceptable for the wife to control her husband when he becomes a cuckold.

So do you buy him nice lingerie to wear . Yes Troy we have an arrangement and I help him to fulfil his feminine desires. It’s nice really I don’t mind and I suppose if he was not so feminine he may not allow me out tonight. So let’s be glad of that. Yes he will fully dressed up by now as he knows you will be out for hours.

We got to the restaurant and it was really lovely the food was great and so good the ambience was beautiful and it was obvious why it was so hard to get a table. Troy was such a great host to take me out. And we got on so well, I did sense a sexual energy between us but I was trying hard to be safe and ignore it, but it’s hard to ignore a wet pussy

Then he asked me to dance and we went out the music was slow dancing as the loud music would not suit the restaurant Troy was a good dancer and we floated around the room, it was lovely dancing with him he held me beautifully and he pulled me closer as we danced I could not stop he whispered I was so beautiful and again thanked me for dressing in black that black men like their women in black especially if their lingerie matches in black also.

Lisa can I be so bold to ask are you all in black all over... Well yes Troy yes all black . Oh god Lisa you must be so beautiful under that dress. I found my pussy throbbing and wet. You would be my queen in black lingerie

Troy pulled me closer and I could feel a huge cock pushing against my cunt and tummy. I melted into his arms and he lifted my chin to look into my eyes, sorry darling I can’t help it you make me so nice.

Then he kissed me and I just accepted his kiss and was soon returning my tongue into meet his, I moaned as his hand pulled me hard against his cock.

We kissed for ages and played tongue tennis I found I was pulling his head hard against mine. We broke as he said oh darling Lisa I want you so much, I want to make you a real women and we kissed again he had taken control of my pussy it was throbbing for him. We would make such a lovely interracial couple. It’s such a pity you are married.

His cock pressing against me moving in a fucking motion against my cunt. I moaned as he kissed me. Then the music stopped for a break we had been on the floor for half an hour. He had felt my panties and. Suspenders caressing all my lingerie.

We sat down and we were both embarrassed at what happened on the dance floor but we held hands. Oh darling I am so happy you honoured me with your beautiful body and I love the feel of your suspenders and stockings and your sexy satin panties. You are so sexy baby, you make me so hard darling I can’t stop it. Oh Troy don’t say that it’s ok I accepted your advance and I enjoyed you so much, but now we have to be good again.

Troy leaned over and we kissed nice just for a few seconds as there were people all around on other tables. You kiss beautifully Lisa John is so lucky.

And you are so lucky that you are married to a sissy, you must get her a boyfriend it is the ultimate desire of a sissy but they don’t know it until you bring it to the surface and then it takes off and they want a boyfriend as soon as the though comes to mind. Just think even John going out on a date with a boyfriend. Maybe even a black boyfriend.

Lisa

Troy was holding my hand and we were like lovers holding hands we were a lovely looking couple both totally dressed in black yes but I was white and Troy was black, I must say we looked so well together I was comfortable and so wet open pussy with tremendous desire in my pussy. My nice earlier thought of just going with a co- worker for dinner had gone out the door.

I wanted Troy but I could not do that, I promised John it was just a dinner with a co worker. So I pulled back and it had been a beautiful night so why spoil it...Troy I want to thank you for a beautiful night but I did promise John that this night was going to be just a dinner date . It has been beautiful and exciting it’s hard to say let’s finish before it goes further but I want to let John see that we were true to our ideals.

Yes Lisa I will take you home when we have finished I am not going to take you to my little flat..ha ha ha.

Maybe if we are good we may get another chance to go out again, yes Troy I would like that very much it will be easier to get John to agree if we are good this time, ok darling let’s head home to John when we are finished, she will be in her lingerie when you get home, yes Troy but she will be stressed if we abused out time out.

Later Troy kissed me as we walked to the car park it was hard to stop we leaned against the car kissing as Troy pressed his large hard cock against my cunt which I did not pull back but pressed against him in return.

oh darling you are so ready for me, I want you baby, I can’t help it you are so sexy, I kissed him hard as his hand went under my dress and felt my wet pussy making me pull his mouth harder on mine, his fingers driving me mental, i wanted him there and then. But we stopped and he said I see you are shaved to please your lover how did you know black men expect their women shaved smooth....we got in the car he drove me home we were both so sexy .

I put my hand on his knee and carressed his thighs I left him know he had pleased me so much. Outside the house I kissed him when we stopped not thinking that John would have been watching inside a darkened front room we kissed and then I said we must stop Troy.

We will get out again if you want . Yes I want you darling I want to take you out mid week please we want each other so much darling. You need to dream of the pleasure of a big black cock

Do you want me darling please say yes Lisa please say yes we will be good again. I will bring you home safe. We may kiss again as we both like it but that will be so nice.

You have to make John a real sissy you must get him a vibrator to use on himself and also a false vagina get him to use it with his hand on his cock he slides it up and down his cock it’s very realistic and he cums in it like masturbating into his hand.

Also ask her did she ever think of been with a man to please her a dominant man even a black man

Good night darling and kissed Troy again for the last time tonight. I went in to find John in the hall oh darling so lovely to see you, oh Lisa I am glad you are home so early yes darling I told you it was just dinner and we had one dance. How was everything Lisa.... Ok baby John let’s get into bed it’s nicer if I tell you there in bed.

We were both in our nightie and I cuddled into John well we had a lovely night darling we had one dance just and a beautiful meal I hate to ask how much it cost but I think it was expensive and full not a table free, restaurant was full, with nice dancing.

What was he like to dance with oh nice darning very sexy dancing and he was like all men his cock got hard against me I said nothing and ignored it happening. It’s common with all men. You do it your self.

I saw you kiss him darling oh it was just a thank you kiss John after all it was a lovely night out and it was just a good night kiss but it was nice. He was such a lovely man a gentleman, I promised I would go out with him again, he did not ask me I told him as a workmate I would take him out next week maybe Wednesday just for after work drinks..

I noticed John’s cock had grown really hard against me so I caught it in his nightie and panties I pulled him to me and told him fuck me John, his cock came over me and soon entered my pussy . Oh Lisa you are so open and wet. Yes baby that’s from been out with Troy, but you get the benefits not him, so just think when I go out with him I come home with a wet pussy for you.

Darling you will need to shave my pussy every 2 days to keep it smooth. You like my pussy hair free baby oh yes Lisa I love It. John Troy did make me sexy for you. Thats why I got so wet... He was so handsome tonight and oh wait till I tell you judging from what he pressed against me he must have a huge cock John, huge I would say and it made me wet.

Did you dress up darling . Yes Lisa as soon as you went out, and how many times did you cum, oh twice Lisa I hope you used the towel and not wet your lingerie oh yes i did Lisa so not wet lingerie. Oh baby keep fucking me as you talk to me harder baby that it push fully in me darling.

Darling I must get you some sex aids actually masturbating aids for the nights I am out with Troy so you can really enjoy masturbation on your own. Otherwise if I am out with Troy you might want to have a man with you to play with each other.

Then John exploded hard in me fully calling me a fucking slut telling me I was his slut... and I was so close all night that I came also so easy as he said oh fuckkkk fuckkkkk Lisa I love you so much, thanks John cum baby fill me ...and even thought I am going out with Troy again next week ok baby, yes Lisa oh Fuckkkkkk Lisa yes yes yes good girl john just after works drinks a few hours....

. I shouted out loud and made a big mistake on purpose ...as I said oh yes fuck me Troy oh yes fuck me hard....Lisa you said Troy, no darling I did not ...you did Lisa . Oh sorry John I did not know why I should do that I think just we were mentioning his name so much and I was calling him Troy all night. I did not mean anything darling.

Are you really going on a date with him again no darling it’s not a date it’s just a meeting of two workmates after work.

I think next week maybe Wednesday we are going out just for a few drinks after work and maybe a bite so you won’t need to make dinner for me , and I will get a taxi home as with drinks he will not be able to drive so don’t worry baby, you will get dressed in lingerie when you get home from work and in the meantime i am getting nice sex aids to make you feel really special

We both collapsed asleep in no time.....

John...........

I was exhausted from the night before, it was the stress the Lisa was out on a date and yet I was not upset because she was on a date with a black man. This was the peculiar thing. I was stressed from the dressing up as soon as Lisa went out with Troy.

As soon as Lisa had gone out iI was delighted to go to my dressing bedroom and get totally dressed in lingerie and tried so many of Lisa skirts and dresses. I masturbated twice and was so excited all the time. I was not even thinking of Lisa and Troy that was the amazing part.

When I got up Lisa had gone shopping as it was Saturday she had left me lie in...I was comfortable in my nightie and panties and I was rock hard again, I played with my cock and I got excited thinking of Lisa kissing Troy a black man and soon I was erupting a beautiful cum as I thought of their lips together kissing and the connection..... i realised I had wet my panties and nightie. I had to get them in the washing machine before Lisa got home.

Lisa......

As I shopped I could not get Troy out of my head. I thought about last night and how we kissed and danced , how much he turned me on and actually I left him touch my shaved pussy almost making me cum. Now I am going on a date again for Wednesday night no discussion about where we were going, I just said yes, I wanted it , without even telling my husband, without asking him.

When I got home John was up I asked him how last night had been and he was shy and told me he had a lovely night, he was apologetic for having put on some of my skirts and dresses, told him don’t be silly my clothes are his to use at any time.

I asked him about exactly what he dressed in he explained he put on so much lingerie and so many skirts and dresses. I was happy for him as he was really turning the way I wanted her to go

What I noticed from John was he was only interested in what he did last night and obviously how much she enjoyed dressing as a women ...oh god I just called John “She”

He was not worried about what Troy and I did, that was for me a great sign that he had accepted as it was ok for me to go out with Troy. I told him last night I was going on a date with Troy on Wednesday but so far he has said nothing about that. No ! all that was on his mind was about his evening and playing as a women.

So I kept on that subject and then retold him I was getting him more lingerie and some sex aids on Monday that would make his dressing so much more exciting when he was at home if I was out with Troy.

I expected him to ask about my upcoming date with Troy, but no! he asked me what sex aids I was getting him, I said Agh that a surprise darling some special presents for my best girlfriend. You will have to wait until Monday, and you can try them out with me on Monday evening, and then you can have so much fun with them on Wednesday when I am out with Troy

But I won’t be late so I will text you when I am coming home to see how you are enjoying yourself.

Oh Lisa I forgot why are you going out with Troy on Wednesday night, I thought it was for one night only, are you sure about this Lisa.

Yes dear quite sure it’s harmless I enjoyed his company last night and he paid so much money for such a short evening that I thought that I would like to sit and have a chat with him again he is very interesting I suppose been older, but again darling I won’t be late but you will have lots of time for dressing as the women you are. And playing with your new sex aids.

Its nice for him to have a friend that he can chat too like me. We never get a chance to chat too much at work. Well Lisa as long as it’s not a regular thing that he expects you to meet him on a regular basis oh no darling nothing like that, just friendship and I feel it’s nice for you to have home time to dress up and play with your new toys.

Ok darling let’s enjoy our weekend and maybe we could go for lunch out tomorrow for Sunday lunch that would be nice don’t you think, yes baby we will do that.

The weekend was nice and it was lovely to be in bed with my girlfriend in her nightie and panties. We did go out to a nice restaurant for Sunday lunch, Ann had her best lingerie on her and was horny.

Sunday night in bed we were lying chatting and suddenly I remember back to when I thought of John as a “She” so I thought maybe it’s time to see if she would like a female name.

I asked John beside my name “Lisa” what other girl names do you like. , oh Lisa a girls name that I like....well let me think I actually love the name “Ann” short for “Annette”. Great I like it too so that settles it.. Ann it will be... short for Annette.

Lisa how do you mean...well Ann in the house and in private with me your new name is “Ann” what Lisa how or why ???.

Well because you are a girl now darling and I think you need a girl name and as you like Ann than let it be Ann . So no more discussion...I want you to be Ann with me in the house.... ok Ann so, ok Lisa that’s settled... now Ann fuck me as this new name has made you tent your nightie and panties girlfriend.

So Now John was Ann and she seamed to like it she did not protest to strongly and I am automatically thinking of her as a she ,

I laid back as Ann got over me I was very wet and just wanted cock in me we pulled out nighties up so we could fuck and she entered me hard and fast as soon as she got in position. Oh good girl Ann fuck me hard darling.

Ann hurt me cum in me, I need you baby Ann fill me up darling, she drove hard in me up and down going quite deep but not able to reach my cervix as she was small as some cocks will go all the way to the womb...

I pushed against her I loved her in me and feeling her explode in me, cum baby cum in me I pushed against me, good girl Ann that’s it...then I said the magic word knowing it would put her over the edge...Troy would be lucky to have a pussy to fuck like you....Troy he does not a pussy to fuck.

Oh Fuckkkkkkk darling I’m cumin. And Ann pumped into me, I knew mentioning the word Troy would start her off, yes Ann girl fill me, I think Troy would love to do that . Oh my god Ann your so strong ...yes hurt me yes yes fuckkkkkkk me Ann yes I’m cumin with you together good girl....I love you....it’s so strong....then we slowed down.

As we stopped Ann said oh darling I forgot the towel. Never mind we will put them all in the washer in the morning....Ann in the morning we have work so let’s get sleep.

Monday

I was in work early where I met Troy, who asked me how did the weekend go with John, I replied you mean Ann he knew immediately what I was saying and asked did she mind I said no she loved it, in fact it was her choice and I like it a lot. It suits her and I love her lots. It’s Ann short for Annette, oh Lisa that’s a lovely name

Oh that’s great. I am looking forward Lisa to taking you out on Wednesday, oh Troy... Lisa ...no ..oh Troy you promised to come out please, well ok to be honest I told Ann and she was ok about it but I was not to stay out late but it was not to get a habit , I told her she would have to shave me again as I did not like stubble. But he loves it good girl Lisa always keep your pussy shaved.

You never know you might meet a black man some day . And you know they expect their women to be shaved... Oh Troy your so naughty. I know Lisa. But I like been naughty....I am getting Ann some toys today, oh good can I please go shopping with you. Maybe so... as you can help get the right ones I am not used to going in sex shops.

So at lunch time we slipped off to the sex shop which was only 2 blocks away.. I was embarrassed and Troy guided me, we picked out Butt plugs a set of 3, so you start with the small one then progress up to the third...after that came the vibrator section there were so many of them.... we choose a medium size.. Troy said it would be suitable for Ann or me. I laughed, then he said to get him off intercourse a bit but still enjoy a vagina so we choose a false vagina.

Troy said I suppose not too long as he might be on the short size I said about 5 inch. Troy said up or down, I said up oh small so.

Troy said they are so realistic and I know he will love them, I know someone in my last job who had one and he told me it was fantastic.

It was amazing I did not even know they made them but yes, they are hand held and he would push it over his cock up and down and masturbate with it. The inside was feeling so realistic as Troy made me put my finger inside, it came with a jell and it looked very much like a vagina with the two vulva lips which gripped the cock as it went in ...god it was so soft and realistic Ann is going to love it. It was not small it would almost big enough for his 2 hands to hold it.

Then joking I said Troy I don’t want him to get too fond of it he might neglect me. Oh darling we have a remedy for that should it arise and ever so quick he pushed me against the shop wall and kissed me hard.

I responded and his tongue on mine and he held me so tight, the shop was quite and no one was there to see us, darling Lisa you will never be without cock you need it. I was getting instantly wet and suddenly we stopped as we had to get back to work..

That night I got home Ann was dressed in her lingerie and a skirt and top. She had dinner ready, I said you look wonderful dear, oh Ann I got you some presents to day, but we will look at them later at bedtime. Oh Ann in future I would suggest that when your dressed you put on a little perfume and some lipstick you are mature enough now for a little make up. Ok Ann... yes Lisa I would really love that.