“Are we ever sure of ourselves”
The beginning.
I had stopped outside a store on the street to look at the display in the window. It was so well presented and so full of color, it was a quite afternoon and very few shoppers around, I stood looking at the beautiful display in the window.
You see it is our wedding anniversary in 2 days and I want to get her a nice gift, I had already got her a lovely card expressing my devotion and love for her.
As I stood looking at 4 beautiful mannequins each one dressed in exquisite silky satin and lace lingerie, each having a Bra and panties with suspender belt and stockings. They were much the same but in different colours, there was white, black, pink, and lemon maybe yellow.
They look so beautiful and so sexy, I was thinking of my wife Ann dressed in one as she likes silky sexy lingerie, I wanted to get one for our third wedding Anniversary and as we were going out for dinner she could wear them that night.
I was so engrossed in the display in front of me and thinking I would love to have Ann looking so sexy, I started to get an beautiful feeling in my cock. As I love the look and feel of silky sexy lingerie on Ann and even on occasions I have masturbated using Ann’s silky sexy panties, the satin on my cock makes me so much harder and I have a stronger climax.
I was in Dreamland looking at the display when I heard a voice say “For your girlfriend”
I came out of my trance totally shocked and embarrassed turning I was face to face with a tall good looking black man.
I started to stammer and said oh sooooorry excuse me, it’s ok I could not help looking my self they are beautiful your girlfriend would love them. I like the way two of the mannequins are black women.
Instead of walking away I was frozen to the spot having been caught looking at woman’s underwear by a man, to make it worse I said no not a girlfriend its for my wife, it’s our Anniversary in two days, but I could not buy them as I would be too embarrassed to go shopping for lingerie.
Oh don’t be silly the tellers are used to men buying lingerie for women and maybe even for themselves, as a lot of men are crossdressers or married sissy’s, and there is nothing wrong with that either so no need to be embarrassed.
Standing there I was about to walk away and the man said what colour hair has your wife I replied blond, oh beautiful then definitely get the lemon set it will match her hair so well she will be so beautiful. I said no I could not go in to buy it I would be too embarrassed, oh don’t be silly there is nothing to be embarrassed about.
Just think of your beautiful wife dressed in that outfit oh my god she will feel so sexy.
No I couldn’t I am too shy when it comes to that, ok stop wait I am Jerome what is your name... Frank, ok Frank fine come on let’s go I will buy them but you can pay just follow me. He actually held my arm and guided me into the shop ignoring my protests. Once inside he went straight to an assistant and asked her about the display in the window as we wanted to get a set for a lady friend.
She asked him what size and colour as they was a slight difference in each set which one did we want. Jerome did all the talking he was not shy in any way, and turning to me asked for the sizes I knew her size and told him 36c bra he said “nice”, I told him pantie size 12 as she was tall the stocking would want to be tall fitting, the assistant knew what she needed , Jerome told her lemon colour but the same as the white set which showed more lace edging that the lemon set on display do you think she will like that Frank.
I replied yes Jerome. He said perfect so he told me to sit in the waiting area while he sorted everything out with the lady.
I went and sat down finding I was quite excited my cock was half full and I could not stop it expanding even though it was slow. I saw Jerome chatting to the assistant and after a long time to went with her to the checkout then he called me for my credit card which I presented for payment.
I got a bit of a shock with the price but at least I could afford it.
My semi hard erection went down rapidly after hearing the price but my Ann deserved it, the assistant had everything ready in a beautiful presentation box really feminine and with a lovely pink bow tied around the box it looked a really lovely gift in its presentation.
Not understanding what had happened in the last 25 min we walked out of the shop. Jerome turned to me and asked me was I happy now I said yes thank you sir, he said yes I am a little older than you but call me Jerome, not Sir, I am not your master... yet... laughing.
Ok let’s go in here to this coffe shop for a relaxing coffee then you can head home to your darling wife, oh Jerome I can’t take up more of your time, it’s fine Frank, I loved helping you and like you I also love ladies silky lingerie.
Over a coffee we chatted and I got to know Jerome quite well he asked a lot about me and Ann he was very friendly and we got to know each other.
I told him we were going out for a Anniversary dinner to a top class restaurant/ dancing bar.
He was a marketing manager for a large company in IT. I told him I was working at the moment but not in the position I like and I was not happy there, Also that Ann had been laid off from her job. He asked for my phone number And he phoned me said don’t answer but I now had his number.
Frank if anything comes up in my company i would let you know and at least you could apply for an interview, also for your wife Ann maybe something will come up in the accounts dept as you said it’s her expertise.
After 2 coffees we parted company and he told me if I ever need help buying a lingerie present for my wife Ann just call him he told me to enjoy my anniversary dinner in 2 days and to enjoy Ann in her beautiful lingerie.
He told me he often buys panties and French knickers as he hates boxers and panties are so much more comfortable, he said he loves the silky feeling and that I should try it. He said he was not gay or a crossdresser just an admirer of silky sexy panties and a lover of women.
Frank have you ever worn panties belong to Ann the question froze me and because I took so long to reply he said I take that as a yes. It’s so lovely Frank doesn’t it feel so sexy to play with them... I love them.
I had got hard by the way the conversation was going, then he said get rid of your silly boxers and wear beautiful sexy satin panties.
Frank I can see you are excited, it’s ok nothing to be ashamed off, I am wearing panties now Frank and I can tell you it’s wonderful.
Jerome put his hand on my thigh and said you are such a pretty boy. You even look a lot feminine and you have a lovely ass.
So I think you should wear some of Ann’s panties until you get your own, I think she would be happy for you, I see how hard you are after getting Frank do you feel good.
Mmmm kinda yes Jerome I am sorry I could not help it. It just happened it’s ok darling we men have that problem sometimes.
Jeromes hand moved on my thigh and he was now moving up to my bulge, I could not do or say anything I was frozen with my head bowed in a submissive manner. I was so shy at what was happening.
Luckily we were sittin in a corner table where we were not obvious as I suddenly panicked but no one was looking our way.
You are feeling so good now Frank aren’t you, oh god Jerome we must stop, but Frank are you feeling good...yes Jerome sir please don’t. I am not Gay Jerome please.
But instead of stopping Jerome hand went to my bulge and pressed hard, oh you are such a sexy hard young boy, Jerome took my hand and placed it on his cock bulge look what you have done to me Frank.
Oh god it’s lovely Frank I feel so sexy in my panties.
I could feel a very large cock inside his bulge as he pressed my hand against it. That’s a good boy, I would love to make you a sissy.
My cock jumped against his hand when he said that, oh Frank you like that idea of been a sissy wearing beautiful lingerie don’t you say it Frank come on tell me you would like to wear lingerie. Say it Frank .....oh fuck yessss as I was going to cum in my pants if I did not say yes .. good girl Frank at least your honest, now say it again as he pressed his hand hard against my rock hard throbbing cock... say “yes sir”.
Oh Jerome...yes sir. Oh you such a good girl Frank, after that my cock started to leak a lot of cum as it throbbed under his hand. Are you cumin darling . Oh fuckkkk Yes Sir, good girl let it all out darling then my cum just poured out as he made a movement against my bulge. Oh Frank you are such a good girl, my girlfriend
Now I think it’s time for you to go home to your darling wife Ann. But I don’t think your white little cock will be going into her white married pussy tonight.
He reached into his carry bag and squeezed a panties into my hand, now go to the gents and change out of those wet boxers and put on these lovely panties, you can’t go home to Ann with a wet patch on your pants. So go now and change.
When I came back Jerome and I walked out and as I said good bye he caught my hand and said you are such a girl now you know it, it was a wonderful cum for you I know you enjoyed it, tell me you did before I go Frank. Yes sir I did and I cannot believe it. Frank I am sir to you now as now I am your master.
Frank see you soon again remember as master says from now on wear Panties, before I could react he quickly kissed me on the lips. I stood there frozen to the spot as he walked away ...
Thinking but he said he was not gay.
Me Frank.
Well it’s about time I told you about my self. I am ,22 and my wife is 24, I am small in stature not tall, I am a gentle person, very shy, with a 5/6 inch cock when hard. I am submissive type will do as I am told. Very kind and helpful to everyone.
I am easily humiliated I like to masturbate and especially with Ann’s silky sexy satin panties in my hand, as I rub my excited cock to climax. I love watching Ann get dressed every morning and evening going to bed, I think it’s her wearing her lovely lingerie I like most .
Shape wise even Ann tells me I have a girly ass, and has asked me why I always sit down to wee like a girl, while men usually stand but girls sit. I admit I don’t know it’s just habit I suppose. She has stopped asking me.
Ann my wife
Ann is so beautiful taller than me very shapely beautiful breasts 36c full pointed with big nipples which expand over ½ an inch when excited. She has a lovely Brazilian bubble ass and could be a model, she is very sexy , she loves sex, loves a cock in her pussy and loves to feel it explode inside her as deep as possible.
She is therefore on the pill as we are not ready yet to breed. We get on so well and have a very good sex life
Ann Is an Alpha female, she was training to be a nurse but never finished she experienced some attention from Doctors and other staff as she was so beautiful. She did have sex with one or two doctors when she was only 19 but nothing serious.
So here I am now at home with Ann having given her gift, Jerome had told me not to tell Ann about him been involved in buying her gift, so I said nothing and pretended I bought it not to mention him.
I hoped she would like it and I did tell her she could open it now in the bedroom while I showered and got ready for bed, I said I was so happy to make her look so nice for our night on the town.
That I have to admit it took a lot to come out to you that I like lingerie so much so please wear it and enjoy it.
I had my shower and came back in naked to get into my pyjamas , all dry and ready for bed. Ann greeted me with so many kisses, she said oh my darling I am so happy that you have come from the closet i love you so much Ann was naked and she had opened the box of lingerie.
The set for the night out she put it in her drawer for when we’re are going to dinner in a few days.
Ann said I adore our special present I presume they are for now darling, I looked in bemusement as she had 2 panties pink in satin lacy and two matching ¾ length silky satin and lots of lace nighties lying on the bed side by side
So on one set was embroidered “His” on the other was “Hers” the same on the panties. Oh darling you are so brave to come out to me and to bring them home for us to wear.
So come on Frank girl put them on she handed me the “his,” and proceeded to put on “hers”, I said nothing and knew now why it took Jerome so long with the assistant I just said Ann I hope you are not disappointed with me, oh darling no I love you so much but I always knew there was a girl in you.
I know you have played masturbating with my panties and I never minded, but now I am glad you got your own lovely panties, and I want you to go out and get some more for yourself then you can masturbate with your own panties.
Darling let us girls get into bed and play in our nighties and new panties darling you are such a brave girl to go shopping for your gift to me and these lovely bedwear.
So now I want you to go out after work tomorrow and get lots of new panties, also some french knickers, get another set of nighties our size and in fact I will make a list, we will throw away all your old boxers I hate them.
Lie down my darling, I laid on my back and Ann knelt on each side of my thighs she lifted my nightie up to my waist ******** my pantie covered hard cock, she lowered her head and kissed me then she whispered; darling start to masturbate yourself come on baby do it for me show me how you do it to yourself. I want to watch.
She sat back on my legs and put my hand on top of my cock, now darling make it nice, I started to caress my satin covered cock and I moaned as I got harder and harder, oh darling thats lovely to see you masturbate yourself it’s very sexy, I am getting so wet darling,
Ann slipped her fingers inside her panties and I could see her fingering her clit, and then her wet pussy. Oh this is so good my baby, then her hand was up her nightie holding her breasts and playing with her nipples.
See me darling I am so wet this is so good , don’t cum yet baby wait we will come together hard, we have to practice like two girls masturbating together.
But Ann do you not want my cock in your pussy. Oh no darling not now this is wonderful, this is better in some ways
We were both masturbating ourselves and then Ann said wait and she lay down side by side. No keep going and Ann lifted her nightie like mine. She pulled her panties down to ****** her clit and pussy.
The she started to moan as her fingers found her clit and her open pussy.
Frank darling I am getting close it’s so good you becoming a girl, oh I love you girlfriend. Yes Ann I am close also, ok baby moan with me tell me your a girl and cum.
I started to feel my cock expand and I knew it was going to explode soon, I shouted oh Ann darling I am a girl yes a girl yesssssss oh Fuckkkkkkk yes Ann I love you.....as Ann watched me she saw me explode inside my panties using my hand.
Your so good at that darling we will do this again I love watching you.
Then I heard Ann scream as she too bounced off the bed with an orgasm, saying yes Frank oh fuckkkkkk so fucking good, oh god fuck so good oh Fuckkkkk as her fingers went deep inside her wet pussy.
Oh thank you babe thank you and we both lay exhausted. I loved watching you fingering yourself Ann it was so sexy.
We turned to each other kissed and said so good, we are going to be so good together from now on darling we are best girlfriends. Frank I am going to train you but I think it’s going to be easy as you are such a girl already.
We cuddled in our sexy nighties and panties and slept so sound.
In the morning we kissed and chatted for a little while, Ann said I am going to make a list of what you need to get today in the ladies department store. Frank do you mind me asking but as I know you are feminine have you ever had any experience with a man. Oh no Ann I never thought about it.
But Ann may I ask you the same question have you had any experience with a woman, yes Frank when I was training to be a nurse I had a small affair with another nurse it was not for long and yet it was lovely. She loved my body so much.
The next day
I went to work and In the morning I got a call from Jerome, he asked did I enjoy the nightie and panties. I said he was very naughty and I explained everything that happened in detail as a result of what he did.
But that now I was in trouble as Ann had given me a list of lingerie shopping to get. But there is no way I can go back to that shop or any other shop for that matter.
Jerome said darling you will meet sir at 5.30 after work at the same shop ok, I will do the shopping for you with you.
I hope you will be wearing panties like I told you, I told him yes that Ann had made me wear a pair of hers to work until I got my own. She is throwing out my boxers.
She is the best girl we will chat later today about everything
I was very nervous and embarrassed meeting Jerome again after what happened the last time but I was desperate to not have Ann find out I was afraid to go lingerie shopping. But I would not go for coffee again with Jerome.
So 5.30 came and there was Jerome waiting for me let’s go shopping, ok where is the list Ann gave you.
We went straight to the ladies lingerie section Jerome with list in hand. First a dozen Panties pick the ones you like and the colour you like, let’s start with real girl pink, then white, black, red, purple and whatever takes your fancy, there were different styles some more lace than others I was the same size as Ann.
Jerome made me text Ann to say I would be late as I had so much to do and I was late starting. She replied girlfriend take your time come home when ready.
But when it came to stockings on the list I would not be as long as Ann. Suspenders and a bra to fit me, Jerome got a tape from the assistant and measured me, he said not to worry about filling them as our next shop would take care of that.
So we had a dozen Panties 4 pairs of stockings another 2 nighties 2 suspenders
So we got lots of lingerie then Jerome went to the skirts area and picked out a mini skirt. I am not going dressing in a skirt Jerome only lingerie. You will need one at home with Ann for evening or weekends. So let’s get one anyway Ann can wear it
Then we came outside after paying for everything with of course one mini skirt. And headed to another shop just up the road, we got 2 pairs of silicone breasts. It was a sex shop.and they were so cool I could not wait to try them on.
Then Jerome led me down to the back of the shop to what he called the changing room, he put some money in a slot and the door opened it was a room with a sofa and a TV. The T V was showing a blue movie of two gay men, Ok let’s try the bra and the implants.
He lifted my polo shirt off me and I was naked on top he then put one of the bras on me, standing behind me he slipped the implants into the bra they filled the breasts up but he thought they were a bit on the small size. So he went to the shop front and told the assistant he was changing them for bigger ones, he came back and again from behind me slipped them into the bra pockets, now they filled up the bra beautifully.
I could see a wonderful pair of breasts sticking out in front of me so realistic. As we admired them in the large mirror Jerome was holding them fully in his hands . He was massaging them like a man would do to his wife.
Then he kissed my neck and told me I was becoming a lovely girl he whispered in my ear how Ann will be so proud of me. I felt my cock getting huge again as I looked in the mirror. Jerome was now pressing his hard cock against my ass and his hand went to my Bulge. I said Jerome Ann is waiting for me it’s ok baby girl she knows you will be late . You are with your master now and I am going to please you and make you a real girl.
His hands were opening my pants which fell to the floor, I stood in my panties they were white as Ann gave them to me very lacy and sexy.
Oh look darling in the mirror look at your girl panties and your full woman size breasts, we will have to get a cock cage to hide your man cock, and stop it getting an erection when you are in your girl clothes.
His hands were now carressing my cock and then he lowered my panties as he took his pants off I felt his naked cock against my ass his mushroom head pushing at my anal passage.
He walked us over to the sofa and told me to hold onto the back as he pulled me back in a standing bending position. He went to his bag for something and came back, he put something wet all over my backside at least it felt like that, but it was really in my ass crack. He stood behind me he been taller than me.
His cock came back and it moved up and down my ass crack it felt wonderful and the wetness made it slide so sexy. I could not believe what was happening to me, but it was beautiful I wanted more.
He was holding my hips and pulling me back against his cock which was riding up and down my ass crack it was hot. I was actually loving this new experience.
He was talking to me telling me how lovely my white ass was and how his black cock looked so well in the crack of my white ass.
He said he owned me now I was his and I would be his lover, he said he would teach me to be his women and I would do whatever he wanted.
He was teasing my hard cock but did not want me to cum. I was close so close at times but he was edging me. His cork was moving in shorter motions and started to push at my ass hole it was not sore or discomfort.
Then he pushed hard and his cock head started to move inside my butt hole. I started to move forw away forward from the intruder but he caught around my waist and pulled me back hard against his cock.
His cock started to go into me and it seemed to hit a barrier, he stopped and then told me it would be sore for just a short little while, but that if I was a good girl and not make much noise he would be easy on me .
He was going to make me a real girl and I will thank him after. Then I felt him drive his rock cock through the barrier and I screamed as I felt him slide deep into me, his balls were now touching my ass and legs.
Oh god he was fully in me the pain was unbelievable when he got fully in my bowels he stopped moving, the pain slowed down a bit and as it did he started to move in me a little, the pain continued to slow and he moved faster the pain started to go away a bit more.
Then he pulled out to the edge and he put lots more wetness on his cock, when it went back into me it was easy and there was no pain I soon found the pain changed to pleasure. Now baby you are a girl. Move against me show your master you want me.
I moved against his cock and the pain was gone it felt so good as his big wet cock got faster, I could feel his cock expand and then after many drives into me I felt him explode inside me he was shooting his cum deep into me oh fuckkkkk. I shouted yessssss sir
Fuckkkkk it was a feeling like no other I had ever experienced and I did not want to stop but soon he pulled out on my ass and turned me around he held me and kissed me hard on my mouth and I kissed him back with passion had I turned gay.
After as we dressed I asked Jerome am I gay now, no darling you and I are not gay I fucked you as a girl you are a woman now, and will become more and more a woman . You will ask me to fuck you again and soon as you become more a women.
You will want oral sex with Ann more not intercourse as you are a girl you will want to have lesbian sex, you have to tell Ann as you feel more a girl that can she do lesbian sex with you. But you know she will need a cock in her sometimes, so maybe you will get a strap on for you to fill her.
You will eventually become a sissy cuckold.
You are my girlfriend now and I am your boyfriend, your master, I own you now your pussy is mine.
Ann’s pussy is only now for your mouth and your tongue or someday you might be kind to her and let her have someone else’s cock to keep her happy you love her so much you will give her anything her desires .
Yes Master I understand Sir I am so happy to have your cum in me, please can we do it again soon yes my bitch you will have me fill you often. I own you now you will soon become a sissy cuckold.
Part 2
Coming soon
“Ann meets Jerome for the first time”
The beginning.
I had stopped outside a store on the street to look at the display in the window. It was so well presented and so full of color, it was a quite afternoon and very few shoppers around, I stood looking at the beautiful display in the window.
You see it is our wedding anniversary in 2 days and I want to get her a nice gift, I had already got her a lovely card expressing my devotion and love for her.
As I stood looking at 4 beautiful mannequins each one dressed in exquisite silky satin and lace lingerie, each having a Bra and panties with suspender belt and stockings. They were much the same but in different colours, there was white, black, pink, and lemon maybe yellow.
They look so beautiful and so sexy, I was thinking of my wife Ann dressed in one as she likes silky sexy lingerie, I wanted to get one for our third wedding Anniversary and as we were going out for dinner she could wear them that night.
I was so engrossed in the display in front of me and thinking I would love to have Ann looking so sexy, I started to get an beautiful feeling in my cock. As I love the look and feel of silky sexy lingerie on Ann and even on occasions I have masturbated using Ann’s silky sexy panties, the satin on my cock makes me so much harder and I have a stronger climax.
I was in Dreamland looking at the display when I heard a voice say “For your girlfriend”
I came out of my trance totally shocked and embarrassed turning I was face to face with a tall good looking black man.
I started to stammer and said oh sooooorry excuse me, it’s ok I could not help looking my self they are beautiful your girlfriend would love them. I like the way two of the mannequins are black women.
Instead of walking away I was frozen to the spot having been caught looking at woman’s underwear by a man, to make it worse I said no not a girlfriend its for my wife, it’s our Anniversary in two days, but I could not buy them as I would be too embarrassed to go shopping for lingerie.
Oh don’t be silly the tellers are used to men buying lingerie for women and maybe even for themselves, as a lot of men are crossdressers or married sissy’s, and there is nothing wrong with that either so no need to be embarrassed.
Standing there I was about to walk away and the man said what colour hair has your wife I replied blond, oh beautiful then definitely get the lemon set it will match her hair so well she will be so beautiful. I said no I could not go in to buy it I would be too embarrassed, oh don’t be silly there is nothing to be embarrassed about.
Just think of your beautiful wife dressed in that outfit oh my god she will feel so sexy.
No I couldn’t I am too shy when it comes to that, ok stop wait I am Jerome what is your name... Frank, ok Frank fine come on let’s go I will buy them but you can pay just follow me. He actually held my arm and guided me into the shop ignoring my protests. Once inside he went straight to an assistant and asked her about the display in the window as we wanted to get a set for a lady friend.
She asked him what size and colour as they was a slight difference in each set which one did we want. Jerome did all the talking he was not shy in any way, and turning to me asked for the sizes I knew her size and told him 36c bra he said “nice”, I told him pantie size 12 as she was tall the stocking would want to be tall fitting, the assistant knew what she needed , Jerome told her lemon colour but the same as the white set which showed more lace edging that the lemon set on display do you think she will like that Frank.
I replied yes Jerome. He said perfect so he told me to sit in the waiting area while he sorted everything out with the lady.
I went and sat down finding I was quite excited my cock was half full and I could not stop it expanding even though it was slow. I saw Jerome chatting to the assistant and after a long time to went with her to the checkout then he called me for my credit card which I presented for payment.
I got a bit of a shock with the price but at least I could afford it.
My semi hard erection went down rapidly after hearing the price but my Ann deserved it, the assistant had everything ready in a beautiful presentation box really feminine and with a lovely pink bow tied around the box it looked a really lovely gift in its presentation.
Not understanding what had happened in the last 25 min we walked out of the shop. Jerome turned to me and asked me was I happy now I said yes thank you sir, he said yes I am a little older than you but call me Jerome, not Sir, I am not your master... yet... laughing.
Ok let’s go in here to this coffe shop for a relaxing coffee then you can head home to your darling wife, oh Jerome I can’t take up more of your time, it’s fine Frank, I loved helping you and like you I also love ladies silky lingerie.
Over a coffee we chatted and I got to know Jerome quite well he asked a lot about me and Ann he was very friendly and we got to know each other.
I told him we were going out for a Anniversary dinner to a top class restaurant/ dancing bar.
He was a marketing manager for a large company in IT. I told him I was working at the moment but not in the position I like and I was not happy there, Also that Ann had been laid off from her job. He asked for my phone number And he phoned me said don’t answer but I now had his number.
Frank if anything comes up in my company i would let you know and at least you could apply for an interview, also for your wife Ann maybe something will come up in the accounts dept as you said it’s her expertise.
After 2 coffees we parted company and he told me if I ever need help buying a lingerie present for my wife Ann just call him he told me to enjoy my anniversary dinner in 2 days and to enjoy Ann in her beautiful lingerie.
He told me he often buys panties and French knickers as he hates boxers and panties are so much more comfortable, he said he loves the silky feeling and that I should try it. He said he was not gay or a crossdresser just an admirer of silky sexy panties and a lover of women.
Frank have you ever worn panties belong to Ann the question froze me and because I took so long to reply he said I take that as a yes. It’s so lovely Frank doesn’t it feel so sexy to play with them... I love them.
I had got hard by the way the conversation was going, then he said get rid of your silly boxers and wear beautiful sexy satin panties.
Frank I can see you are excited, it’s ok nothing to be ashamed off, I am wearing panties now Frank and I can tell you it’s wonderful.
Jerome put his hand on my thigh and said you are such a pretty boy. You even look a lot feminine and you have a lovely ass.
So I think you should wear some of Ann’s panties until you get your own, I think she would be happy for you, I see how hard you are after getting Frank do you feel good.
Mmmm kinda yes Jerome I am sorry I could not help it. It just happened it’s ok darling we men have that problem sometimes.
Jeromes hand moved on my thigh and he was now moving up to my bulge, I could not do or say anything I was frozen with my head bowed in a submissive manner. I was so shy at what was happening.
Luckily we were sittin in a corner table where we were not obvious as I suddenly panicked but no one was looking our way.
You are feeling so good now Frank aren’t you, oh god Jerome we must stop, but Frank are you feeling good...yes Jerome sir please don’t. I am not Gay Jerome please.
But instead of stopping Jerome hand went to my bulge and pressed hard, oh you are such a sexy hard young boy, Jerome took my hand and placed it on his cock bulge look what you have done to me Frank.
Oh god it’s lovely Frank I feel so sexy in my panties.
I could feel a very large cock inside his bulge as he pressed my hand against it. That’s a good boy, I would love to make you a sissy.
My cock jumped against his hand when he said that, oh Frank you like that idea of been a sissy wearing beautiful lingerie don’t you say it Frank come on tell me you would like to wear lingerie. Say it Frank .....oh fuck yessss as I was going to cum in my pants if I did not say yes .. good girl Frank at least your honest, now say it again as he pressed his hand hard against my rock hard throbbing cock... say “yes sir”.
Oh Jerome...yes sir. Oh you such a good girl Frank, after that my cock started to leak a lot of cum as it throbbed under his hand. Are you cumin darling . Oh fuckkkk Yes Sir, good girl let it all out darling then my cum just poured out as he made a movement against my bulge. Oh Frank you are such a good girl, my girlfriend
Now I think it’s time for you to go home to your darling wife Ann. But I don’t think your white little cock will be going into her white married pussy tonight.
He reached into his carry bag and squeezed a panties into my hand, now go to the gents and change out of those wet boxers and put on these lovely panties, you can’t go home to Ann with a wet patch on your pants. So go now and change.
When I came back Jerome and I walked out and as I said good bye he caught my hand and said you are such a girl now you know it, it was a wonderful cum for you I know you enjoyed it, tell me you did before I go Frank. Yes sir I did and I cannot believe it. Frank I am sir to you now as now I am your master.
Frank see you soon again remember as master says from now on wear Panties, before I could react he quickly kissed me on the lips. I stood there frozen to the spot as he walked away ...
Thinking but he said he was not gay.
Me Frank.
Well it’s about time I told you about my self. I am ,22 and my wife is 24, I am small in stature not tall, I am a gentle person, very shy, with a 5/6 inch cock when hard. I am submissive type will do as I am told. Very kind and helpful to everyone.
I am easily humiliated I like to masturbate and especially with Ann’s silky sexy satin panties in my hand, as I rub my excited cock to climax. I love watching Ann get dressed every morning and evening going to bed, I think it’s her wearing her lovely lingerie I like most .
Shape wise even Ann tells me I have a girly ass, and has asked me why I always sit down to wee like a girl, while men usually stand but girls sit. I admit I don’t know it’s just habit I suppose. She has stopped asking me.
Ann my wife
Ann is so beautiful taller than me very shapely beautiful breasts 36c full pointed with big nipples which expand over ½ an inch when excited. She has a lovely Brazilian bubble ass and could be a model, she is very sexy , she loves sex, loves a cock in her pussy and loves to feel it explode inside her as deep as possible.
She is therefore on the pill as we are not ready yet to breed. We get on so well and have a very good sex life
Ann Is an Alpha female, she was training to be a nurse but never finished she experienced some attention from Doctors and other staff as she was so beautiful. She did have sex with one or two doctors when she was only 19 but nothing serious.
So here I am now at home with Ann having given her gift, Jerome had told me not to tell Ann about him been involved in buying her gift, so I said nothing and pretended I bought it not to mention him.
I hoped she would like it and I did tell her she could open it now in the bedroom while I showered and got ready for bed, I said I was so happy to make her look so nice for our night on the town.
That I have to admit it took a lot to come out to you that I like lingerie so much so please wear it and enjoy it.
I had my shower and came back in naked to get into my pyjamas , all dry and ready for bed. Ann greeted me with so many kisses, she said oh my darling I am so happy that you have come from the closet i love you so much Ann was naked and she had opened the box of lingerie.
The set for the night out she put it in her drawer for when we’re are going to dinner in a few days.
Ann said I adore our special present I presume they are for now darling, I looked in bemusement as she had 2 panties pink in satin lacy and two matching ¾ length silky satin and lots of lace nighties lying on the bed side by side
So on one set was embroidered “His” on the other was “Hers” the same on the panties. Oh darling you are so brave to come out to me and to bring them home for us to wear.
So come on Frank girl put them on she handed me the “his,” and proceeded to put on “hers”, I said nothing and knew now why it took Jerome so long with the assistant I just said Ann I hope you are not disappointed with me, oh darling no I love you so much but I always knew there was a girl in you.
I know you have played masturbating with my panties and I never minded, but now I am glad you got your own lovely panties, and I want you to go out and get some more for yourself then you can masturbate with your own panties.
Darling let us girls get into bed and play in our nighties and new panties darling you are such a brave girl to go shopping for your gift to me and these lovely bedwear.
So now I want you to go out after work tomorrow and get lots of new panties, also some french knickers, get another set of nighties our size and in fact I will make a list, we will throw away all your old boxers I hate them.
Lie down my darling, I laid on my back and Ann knelt on each side of my thighs she lifted my nightie up to my waist ******** my pantie covered hard cock, she lowered her head and kissed me then she whispered; darling start to masturbate yourself come on baby do it for me show me how you do it to yourself. I want to watch.
She sat back on my legs and put my hand on top of my cock, now darling make it nice, I started to caress my satin covered cock and I moaned as I got harder and harder, oh darling thats lovely to see you masturbate yourself it’s very sexy, I am getting so wet darling,
Ann slipped her fingers inside her panties and I could see her fingering her clit, and then her wet pussy. Oh this is so good my baby, then her hand was up her nightie holding her breasts and playing with her nipples.
See me darling I am so wet this is so good , don’t cum yet baby wait we will come together hard, we have to practice like two girls masturbating together.
But Ann do you not want my cock in your pussy. Oh no darling not now this is wonderful, this is better in some ways
We were both masturbating ourselves and then Ann said wait and she lay down side by side. No keep going and Ann lifted her nightie like mine. She pulled her panties down to ****** her clit and pussy.
The she started to moan as her fingers found her clit and her open pussy.
Frank darling I am getting close it’s so good you becoming a girl, oh I love you girlfriend. Yes Ann I am close also, ok baby moan with me tell me your a girl and cum.
I started to feel my cock expand and I knew it was going to explode soon, I shouted oh Ann darling I am a girl yes a girl yesssssss oh Fuckkkkkkk yes Ann I love you.....as Ann watched me she saw me explode inside my panties using my hand.
Your so good at that darling we will do this again I love watching you.
Then I heard Ann scream as she too bounced off the bed with an orgasm, saying yes Frank oh fuckkkkkk so fucking good, oh god fuck so good oh Fuckkkkk as her fingers went deep inside her wet pussy.
Oh thank you babe thank you and we both lay exhausted. I loved watching you fingering yourself Ann it was so sexy.
We turned to each other kissed and said so good, we are going to be so good together from now on darling we are best girlfriends. Frank I am going to train you but I think it’s going to be easy as you are such a girl already.
We cuddled in our sexy nighties and panties and slept so sound.
In the morning we kissed and chatted for a little while, Ann said I am going to make a list of what you need to get today in the ladies department store. Frank do you mind me asking but as I know you are feminine have you ever had any experience with a man. Oh no Ann I never thought about it.
But Ann may I ask you the same question have you had any experience with a woman, yes Frank when I was training to be a nurse I had a small affair with another nurse it was not for long and yet it was lovely. She loved my body so much.
The next day
I went to work and In the morning I got a call from Jerome, he asked did I enjoy the nightie and panties. I said he was very naughty and I explained everything that happened in detail as a result of what he did.
But that now I was in trouble as Ann had given me a list of lingerie shopping to get. But there is no way I can go back to that shop or any other shop for that matter.
Jerome said darling you will meet sir at 5.30 after work at the same shop ok, I will do the shopping for you with you.
I hope you will be wearing panties like I told you, I told him yes that Ann had made me wear a pair of hers to work until I got my own. She is throwing out my boxers.
She is the best girl we will chat later today about everything
I was very nervous and embarrassed meeting Jerome again after what happened the last time but I was desperate to not have Ann find out I was afraid to go lingerie shopping. But I would not go for coffee again with Jerome.
So 5.30 came and there was Jerome waiting for me let’s go shopping, ok where is the list Ann gave you.
We went straight to the ladies lingerie section Jerome with list in hand. First a dozen Panties pick the ones you like and the colour you like, let’s start with real girl pink, then white, black, red, purple and whatever takes your fancy, there were different styles some more lace than others I was the same size as Ann.
Jerome made me text Ann to say I would be late as I had so much to do and I was late starting. She replied girlfriend take your time come home when ready.
But when it came to stockings on the list I would not be as long as Ann. Suspenders and a bra to fit me, Jerome got a tape from the assistant and measured me, he said not to worry about filling them as our next shop would take care of that.
So we had a dozen Panties 4 pairs of stockings another 2 nighties 2 suspenders
So we got lots of lingerie then Jerome went to the skirts area and picked out a mini skirt. I am not going dressing in a skirt Jerome only lingerie. You will need one at home with Ann for evening or weekends. So let’s get one anyway Ann can wear it
Then we came outside after paying for everything with of course one mini skirt. And headed to another shop just up the road, we got 2 pairs of silicone breasts. It was a sex shop.and they were so cool I could not wait to try them on.
Then Jerome led me down to the back of the shop to what he called the changing room, he put some money in a slot and the door opened it was a room with a sofa and a TV. The T V was showing a blue movie of two gay men, Ok let’s try the bra and the implants.
He lifted my polo shirt off me and I was naked on top he then put one of the bras on me, standing behind me he slipped the implants into the bra they filled the breasts up but he thought they were a bit on the small size. So he went to the shop front and told the assistant he was changing them for bigger ones, he came back and again from behind me slipped them into the bra pockets, now they filled up the bra beautifully.
I could see a wonderful pair of breasts sticking out in front of me so realistic. As we admired them in the large mirror Jerome was holding them fully in his hands . He was massaging them like a man would do to his wife.
Then he kissed my neck and told me I was becoming a lovely girl he whispered in my ear how Ann will be so proud of me. I felt my cock getting huge again as I looked in the mirror. Jerome was now pressing his hard cock against my ass and his hand went to my Bulge. I said Jerome Ann is waiting for me it’s ok baby girl she knows you will be late . You are with your master now and I am going to please you and make you a real girl.
His hands were opening my pants which fell to the floor, I stood in my panties they were white as Ann gave them to me very lacy and sexy.
Oh look darling in the mirror look at your girl panties and your full woman size breasts, we will have to get a cock cage to hide your man cock, and stop it getting an erection when you are in your girl clothes.
His hands were now carressing my cock and then he lowered my panties as he took his pants off I felt his naked cock against my ass his mushroom head pushing at my anal passage.
He walked us over to the sofa and told me to hold onto the back as he pulled me back in a standing bending position. He went to his bag for something and came back, he put something wet all over my backside at least it felt like that, but it was really in my ass crack. He stood behind me he been taller than me.
His cock came back and it moved up and down my ass crack it felt wonderful and the wetness made it slide so sexy. I could not believe what was happening to me, but it was beautiful I wanted more.
He was holding my hips and pulling me back against his cock which was riding up and down my ass crack it was hot. I was actually loving this new experience.
He was talking to me telling me how lovely my white ass was and how his black cock looked so well in the crack of my white ass.
He said he owned me now I was his and I would be his lover, he said he would teach me to be his women and I would do whatever he wanted.
He was teasing my hard cock but did not want me to cum. I was close so close at times but he was edging me. His cork was moving in shorter motions and started to push at my ass hole it was not sore or discomfort.
Then he pushed hard and his cock head started to move inside my butt hole. I started to move forw away forward from the intruder but he caught around my waist and pulled me back hard against his cock.
His cock started to go into me and it seemed to hit a barrier, he stopped and then told me it would be sore for just a short little while, but that if I was a good girl and not make much noise he would be easy on me .
He was going to make me a real girl and I will thank him after. Then I felt him drive his rock cock through the barrier and I screamed as I felt him slide deep into me, his balls were now touching my ass and legs.
Oh god he was fully in me the pain was unbelievable when he got fully in my bowels he stopped moving, the pain slowed down a bit and as it did he started to move in me a little, the pain continued to slow and he moved faster the pain started to go away a bit more.
Then he pulled out to the edge and he put lots more wetness on his cock, when it went back into me it was easy and there was no pain I soon found the pain changed to pleasure. Now baby you are a girl. Move against me show your master you want me.
I moved against his cock and the pain was gone it felt so good as his big wet cock got faster, I could feel his cock expand and then after many drives into me I felt him explode inside me he was shooting his cum deep into me oh fuckkkkk. I shouted yessssss sir
Fuckkkkk it was a feeling like no other I had ever experienced and I did not want to stop but soon he pulled out on my ass and turned me around he held me and kissed me hard on my mouth and I kissed him back with passion had I turned gay.
After as we dressed I asked Jerome am I gay now, no darling you and I are not gay I fucked you as a girl you are a woman now, and will become more and more a woman . You will ask me to fuck you again and soon as you become more a women.
You will want oral sex with Ann more not intercourse as you are a girl you will want to have lesbian sex, you have to tell Ann as you feel more a girl that can she do lesbian sex with you. But you know she will need a cock in her sometimes, so maybe you will get a strap on for you to fill her.
You will eventually become a sissy cuckold.
You are my girlfriend now and I am your boyfriend, your master, I own you now your pussy is mine.
Ann’s pussy is only now for your mouth and your tongue or someday you might be kind to her and let her have someone else’s cock to keep her happy you love her so much you will give her anything her desires .
Yes Master I understand Sir I am so happy to have your cum in me, please can we do it again soon yes my bitch you will have me fill you often. I own you now you will soon become a sissy cuckold.
Part 2
Coming soon
“Ann meets Jerome for the first time”
