Annie's Room

[SweetAnnie40]

If only I were in the same country... I do get hard, aroused by dressing for and then playing with a woman... so the challenge would be for your hard cock to fill my two holes and mine to fill your three!

Butnonly if we both have our finest garter belt, heels and stockings on xxxx

I wish my hubby had that enthusiasm. First off, we would have lovely lingerie-clad fucking sessions but its been months since he's been inside me with his cock. But that was a special time in this whole process, him fully loving how being in elaborate lingerie, high heels, and princess dresses while we made love and just fucked.

 

[SweetAnnie40]

Bit of a problem here ...

I know from your posts, Annie, that you love a good old suck on a cock

But since hubby has become more Sissy, he has become less drawn to this

You too have been drawn to your new girlfriend, and haven't said much other than you are having fun and falling for her

So my challenge is for you to have a big old cock sucking session and report back - happy for it to be with Sissy Hub or with Strap On Girlfriend

Bonus point if you manage both

I do get a chance to practice my cocksucking skills somewhat regularly. Our friend, Gary, comes over about once a month these days. He spends some time with hubby letting my little sissy suck cock, swallow cum, and then get expertly fucked. Once hubby is curled up in his cum-filled panties, we take a break, Gary and I shower together and I get the challenge of sucking him off for his third cum. It can last awhile so it does exercise all my talents. Most times he can get hard again to fuck me but usually doesn't cum again. If he is just too tired to get hard, he uses a fairly talented mouth which also makes for a satisfying end to my evening.

So yes, my girlfriend gets most of my sexual attention, hubby about once a week or less (mostly because it is hard to get time in the house with him alone).

 

[dacoach44]

My sissy effort........

Had my pink panties, bra and trans nightie; my Montreal lover was gonna put makeup on. But then her kid called, his cursed PC broke. That ruined the mood, and I will have to wait to see if I can get hard in sissy lingerie...........

 

[Sissy_Trish]

Challenge away... and be specific.

Here is a challenge, I had to think about this for a while

Since this is the season to give than receive......It would be kind of nice for you to spread the joy of a blowjob to maybe a stranger with your sissy help if you wish. I was thinking maybe book a room at a nice hotel that has a nice up scale bar to shop for a candidate. Most men are aware of Cuckold relationships so having sissy or hubby there to observe and provide security would not be out of place. Depending on the vibes you get, Sissy/hubby could be dressed waiting in the room waiting, or with you while you shop the bar for your Blowjob candidate. I think it wouldn't be all that difficult with folks having drinks this time of the year to find someone to spread some joy...I'm sure sissy would enjoy this as well an opportunity to be dressed and possibility of helping you service a strange new cock.

https://img-l3.xvideos-cdn.com/videos/thumbslll/da/23/d0/da23d043253833d505f927fec3d89b34/da23d043253833d505f927fec3d89b34.29.jpg

 

[dacoach44]

Wow Annie......

that would be so fun. Get my cute GF to find me some cock..........



https://i.imgur.com/J291rNx.jpg

 

[LucyCanyon]

I wish my hubby had that enthusiasm. First off, we would have lovely lingerie-clad fucking sessions but its been months since he's been inside me with his cock. But that was a special time in this whole process, him fully loving how being in elaborate lingerie, high heels, and princess dresses while we made love and just fucked.

His journey is different to mine I know, and that makes it more difficult for you I can see.... I would soooo enjoy being dressed and appreciated in my finery whilst then being as good as I can at fucking someone in the same style of sexy clothing... the feel of my nylon clad legs rubbing against yours, or your hands on mine as my heels rest on your shoulders and your strapon takes me.... before I return the favour...

Am glad things with your girlfriend are helping your desires... life can be complicated!

.... and here's a starter for you (thanks to Trish for my discreet little logo xx)

 

[Iris_66]

I do get a chance to practice my cocksucking skills somewhat regularly. Our friend, Gary, comes over about once a month these days. He spends some time with hubby letting my little sissy suck cock, swallow cum, and then get expertly fucked. Once hubby is curled up in his cum-filled panties, we take a break, Gary and I shower together and I get the challenge of sucking him off for his third cum. It can last awhile so it does exercise all my talents. Most times he can get hard again to fuck me but usually doesn't cum again. If he is just too tired to get hard, he uses a fairly talented mouth which also makes for a satisfying end to my evening.

So yes, my girlfriend gets most of my sexual attention, hubby about once a week or less (mostly because it is hard to get time in the house with him alone).

I'd forgotten about Gary, and certainly being round 3 certainly tests your skills!

So glad for you that things seem to have settled in your personal life, and you are able to pop up more on Lit. Also that you seem to be settled with your girlfriend and that is all you hoped it would be

Still no movement on the son I guess, but are you still fantasising about his girlfriend?

And it is so great that you are still supporting Hubby on his journey. Like Lucy, I love to wear female, but to have my fun with females too. It's fab that you keep this thread as somewhere we can all go to have fun and hang out x

 

[SweetAnnie40]

Here is a challenge, I had to think about this for a while

Since this is the season to give than receive......It would be kind of nice for you to spread the joy of a blowjob to maybe a stranger with your sissy help if you wish. I was thinking maybe book a room at a nice hotel that has a nice up scale bar to shop for a candidate. Most men are aware of Cuckold relationships so having sissy or hubby there to observe and provide security would not be out of place. Depending on the vibes you get, Sissy/hubby could be dressed waiting in the room waiting, or with you while you shop the bar for your Blowjob candidate. I think it wouldn't be all that difficult with folks having drinks this time of the year to find someone to spread some joy...I'm sure sissy would enjoy this as well an opportunity to be dressed and possibility of helping you service a strange new cock.

https://img-l3.xvideos-cdn.com/videos/thumbslll/da/23/d0/da23d043253833d505f927fec3d89b34/da23d043253833d505f927fec3d89b34.29.jpg

Hmmm, well, I have to admit that sounds pretty hot. I'm enjoying thinking about that. We'll see...

 

[blade_rocknut]

His journey is different to mine I know, and that makes it more difficult for you I can see.... I would soooo enjoy being dressed and appreciated in my finery whilst then being as good as I can at fucking someone in the same style of sexy clothing... the feel of my nylon clad legs rubbing against yours, or your hands on mine as my heels rest on your shoulders and your strapon takes me.... before I return the favour...

Am glad things with your girlfriend are helping your desires... life can be complicated!

.... and here's a starter for you (thanks to Trish for my discreet little logo xx)

You look very nicely put together here, LC.

 

[SweetAnnie40]

His journey is different to mine I know, and that makes it more difficult for you I can see.... I would soooo enjoy being dressed and appreciated in my finery whilst then being as good as I can at fucking someone in the same style of sexy clothing... the feel of my nylon clad legs rubbing against yours, or your hands on mine as my heels rest on your shoulders and your strapon takes me.... before I return the favour...

Am glad things with your girlfriend are helping your desires... life can be complicated!

.... and here's a starter for you (thanks to Trish for my discreet little logo xx)

Beautiful, girlfriend! With those killer legs in sexy heels... very sexy

 

[SweetAnnie40]

Okay, I've procrastinated long enough. What do I get my girlfriend for Christmas? Hubby has no ideas and I'm pretty terrible at gift giving. Not a load of money to spend but I was thinking of a necklace or earrings... what do my girlfriends think?

 

[dacoach44]

Well Annie...

ask her ring size, then go look. Women love that stuff. It dont have to be expensive, either.

 

[dacoach44]

and Annie........

keep in mind the color of her eyes.

 

[Sissy_Trish]

Beautiful, girlfriend! With those killer legs in sexy heels... very sexy

Gifts from the heart that express true love are inexpensive and priceless....

 

[LucyCanyon]

You look very nicely put together here, LC.

Thanks, appreciate that as it's always a little nerve wracking getting close to disclosing the full me and my bad makeup attempts!

Beautiful, girlfriend! With those killer legs in sexy heels... very sexy

Thanks Annie, blushing now but am glad you like what you see... all yours to play with if you make it to Yorkshire

 

[LucyCanyon]

Okay, I've procrastinated long enough. What do I get my girlfriend for Christmas? Hubby has no ideas and I'm pretty terrible at gift giving. Not a load of money to spend but I was thinking of a necklace or earrings... what do my girlfriends think?

Am not great at such things, I might be tempted to go lingerie she can only wear for you, or wear to arouse herself under drab outfits .. only you two know how fine the stockings are or how it's a basque or corset under that work shirt.

But it got me thinking about personal and not costly and appropriately sexy.. and I thought gift vouchers with a difference... each one (however many you can think of ) is a gift to her to be reclaimed at a time of her choosing and is doubled if you can't deliver ... Annie Voucher 1 - Oral orgasm, only your tongue can be used; Annie Voucher 2 - Girlfriend chooses your whole outfit for a day , as many or as few items as she wants; Voucher 3 - Use any toy she likes on you for a time period...

And so on, word them nicely, she can cash them in all the way up to Easter!

Lxx

 

[nassauguy_2001]

Am not great at such things, I might be tempted to go lingerie she can only wear for you, or wear to arouse herself under drab outfits .. only you two know how fine the stockings are or how it's a basque or corset under that work shirt.

But it got me thinking about personal and not costly and appropriately sexy.. and I thought gift vouchers with a difference... each one (however many you can think of ) is a gift to her to be reclaimed at a time of her choosing and is doubled if you can't deliver ... Annie Voucher 1 - Oral orgasm, only your tongue can be used; Annie Voucher 2 - Girlfriend chooses your whole outfit for a day , as many or as few items as she wants; Voucher 3 - Use any toy she likes on you for a time period...

And so on, word them nicely, she can cash them in all the way up to Easter!

Lxx

Excellent suggestions!!!

 

[SweetAnnie40]

keep in mind the color of her eyes.

You don't think a ring sends a message? It would to me...

 

[SweetAnnie40]

Am not great at such things, I might be tempted to go lingerie she can only wear for you, or wear to arouse herself under drab outfits .. only you two know how fine the stockings are or how it's a basque or corset under that work shirt.

But it got me thinking about personal and not costly and appropriately sexy.. and I thought gift vouchers with a difference... each one (however many you can think of ) is a gift to her to be reclaimed at a time of her choosing and is doubled if you can't deliver ... Annie Voucher 1 - Oral orgasm, only your tongue can be used; Annie Voucher 2 - Girlfriend chooses your whole outfit for a day , as many or as few items as she wants; Voucher 3 - Use any toy she likes on you for a time period...

And so on, word them nicely, she can cash them in all the way up to Easter!

Lxx

Classic but effective. Not like she needs a coupon to get anything she wants from me but its the thought... Looking for jewelry this afternoon. If I don't find anything special, I may go with the coupons.

 

[dacoach44]

So Annie..........

Classic but effective. Not like she needs a coupon to get anything she wants from me but its the thought... Looking for jewelry this afternoon. If I don't find anything special, I may go with the coupons.

what color are her eyes?

 

[SweetAnnie40]

what color are her eyes?

Blue, fairly light blue.

 

[BiMale4KinkyFun]

If she is music lover get her favorite album on vinyl. You can find good prices on used vinyl.

 

[stargame]

Blue, fairly light blue.

I am loving this. I wish I could give you both a gift

 

[dacoach44]

Good girl, Annie..........

Its the thought that counts, of course. Red or green, esp at Christmas, would compliment her eyes. A shiny bit of holiday bling for your lover.

 

[SweetAnnie40]

I am loving this. I wish I could give you both a gift

She is so beautiful (heart swelling)