SweetAnnie40
Literotica Guru
- Joined
- Sep 22, 2017
- Posts
- 3,726
Okay this is silly but let's see if it works. I'll take the top ten from my list of Subscribed Threads and weave them into a little story IN ORDER. Challenge you to do the same! The threads are links.
"Hello! Annie's Sissy Help Line!" I said cheerily after connecting to the incoming call.
"Um, hi, uh, I'm so embarrassed," came the lilting but male voice.
"Don't be worried, sweetie, you privacy is assured and I understand. Tell me what I can help with."
"I... I wanna be a sissy so much but I don't have the courage to try it."
"Well, do you live with a female relative, girlfriend, or wife?"
"No, I'm single and live in my own apartment."
"And you just don't think you can take the plunge by yourself?"
"That's right."
"Well, if you lived in (CITY NAME WITHHELD), I could help you out."
"Really? I do, I mean I live in a suburb but I'm really close. Would you?"
"Sure, sugar, I'd be glad to. It'll be a wild ride, but I'll get you past all your fears. I'll text you my address and come over this Saturday at 1pm."
"Uh, do I have to pay?"
"First time is free. If you like it, we can come to an arrangement," I said smiling, seeing the money roll in from yet another "sissy student".
"I'll be there! Thank you! Thank you so much! This is amazing!!"
"Looking forward to it, sweetie. Bye bye!"
It was about time for dinner so I put the Help Line on to auto-answer. I'd recorded a few sexy monologues of myself and sissies usually called to hear those and cum in their panties.
My new roommate, Charlotte was in the living room with the mover and lots of boxes.
"Where should I put this?" asked the mover. It actually was one of my boxes. I'd only moved in two days earlier.
"Oh, you can put that in Annie's Room," directed Charlotte. We'd been friends for years and often 'more than friends' so rooming together had all sorts of exciting possibilities.
After the mover headed upstairs with my box, I came over and gave Charlotte a little pat on the tush. She looked amazing in her leggings and crop top, her white jog bra peeking out trying to contain her large breasts.
"I've got another sissy client on Saturday," I mentioned as began to get nosy with her stuff. I saw a stack of DVDs hand-labeled as BJs finished by swallowing every drop voluntarily. We had similar tastes. "You up for helping out?"
"Sure, I could use the distraction and 'exercise'. Bianca will be here too but she's always up for it," she purred back. I was tempted to start feeling her up right there but the movers were on the clock. The one came back down from upstairs, nodding to me with a smile before heading to the truck outside. He was a finely built younger man with mahogany skin.
"I wonder if he'd like to play. Having a real cock around has all sorts of uses..." I mumbled to myself.
When he came back in with another box, Charlotte stopped him. "Hey, Carl, do you want to come over Saturday afternoon for a lot of kinky group sex?" I think that was the first time I'd seen a black man blanche a little out of shock but he clearly warmed up to the idea quickly. I saw his pants shift and he was a blessed man.
"I'd love to. Just you... two?"
"And another guy. You okay with that?"
"Yeah, I like it all."
"You're in. Show up at..." she began and looked at me.
"2pm" I finished. Carl certainly had pep in his step for the rest of the move-in.
Later, Charlotte and I were cooking dinner and discussing plans for Saturday.
"A total newbie? Starting him with dress up, I assume, but how far do you think he'll go? Pegging?"
"When being dressed up by a pair of Lesbians, I think he'd love to be on the receiving end."
"Do he tell you any of his Sissy Fantasies?" She strained the pasta and I finished spicing the sauce.
"No, but that can be ice-breaker talk. I put that box of big-sized High Heels in the play bedroom so I think locking him into some of those will make it hard for him to bolt and he'll love it."
Saturday came fast as Charlotte and I worked and put our new house together in order. We went for a run together, got back and showered before the 'new one' was going to show up. Again, I had to resist showering with her but we'd still have been going at it when he arrived. Bianca arrived about 12:45pm and got herself a drink while we dressed. She was wearing some of her 'call my Mistress' leathers.
I selected a fairly flirtatious, deep cut top, a satiny teddy, a short skirt, thigh highs and heels. Charlotte went with a bikini swimsuit and skirt and sandals. At 1pm on the dot, the doorbell rang.
I liked what I saw when I opened the door. He had his eyes cast down (already showing submissive deference) and was a slender young man on the short side. He'd fit into... size L in most women's lingerie and clothing I guessed. He was blushing already.
"Welcome to Annie's Realm, sissy. Tell me your sissy name and you may enter."
He swallowed hard, his eyes sneaking gaping looks at me. "C... Candy."
"Alright Candy, enter and become the girly slut you always dreamed of." Again, he was hesitant but he stepped through. "Take your boy costume off and leave it on the chair there."
He began stripping and only hesitated when he was down to his boxers. His cock was small but very stiff at this point.
"Girls, finish him off!" I say with glee as I close and lock the front door. Biance and Charlotte saunter, cozy up against him and before they can pull his boxers off, he moans and cums.
They wait until he's pumped his full load in his boxers and then carefully take them off of him.
"I'm so sorry, Mistress Annie," he began, very distraught. I waved him to silence.
"Honey, it's understandable to get excited. Let me help you." I quickly put his soft little cock into a small chastity and clicked the lock shut.
"Wha.. I don't..." he began to babble.
"It's for your own good, sweetie. This will keep you focused and obedient or you'll wear that home." I went and carefully picked up his boxers. "Now, because you were so 'eager' we're jumping ahead a little. Lesson one will be Eating Your Own Cum."
His eyes grew wide but Bianca and Charlotte laid it on thick and kept rubbing their curves against his body, telling him how sexy it was for guys to eat cum and how much it would turn them on.
Surprisingly, Candy got on board pretty quickly and licked and sucked his whole load out of the boxers.
"Good girl! I'm impressed. Next time it will be out of panties, or straight from the cock!"
"On to play dress up!" I announced, dropping his wet boxers on his clothes pile which Bianca would quietly hide later. I led Candy up to the play bedroom where I'd laid out several panties, stockings, the high heels, bras, corsets and a bustier.
"What looks most girly and sexy to you, Candy?"
She pointed to pink satin panties so I helped her step into them, pulling them up slowly and then snug over her bottom and caged clit. (I always starting thinking of sissies as she by this point). I suggested a matching satin bra and gave him some large, heavy false breasts to place in them. Usually I'd use adhesive to her chest but we'd skipped all the hair removal. Another time perhaps.
Candy couldn't wait to get all girly dressed, putting on thigh highs and the high heels. She began to prance around and gaze at herself in the mirror. Her body had a lot of 'natural talent' which if guided and shaped meant she could be very girl-like in her body and features. Such potential!
This is when Bianca started taking flash pictures with her phone, uploading them to the cloud.
"Wait! Don't.. Nobody can see me like this!" begged Candy, distraught.
"Don't you think she really wants to be Naughty at Work? teased Charlotte, ignoring Candy.
to be continued?!?
Okay, that's eleven for me. Who can beat that?
"Hello! Annie's Sissy Help Line!" I said cheerily after connecting to the incoming call.
"Um, hi, uh, I'm so embarrassed," came the lilting but male voice.
"Don't be worried, sweetie, you privacy is assured and I understand. Tell me what I can help with."
"I... I wanna be a sissy so much but I don't have the courage to try it."
"Well, do you live with a female relative, girlfriend, or wife?"
"No, I'm single and live in my own apartment."
"And you just don't think you can take the plunge by yourself?"
"That's right."
"Well, if you lived in (CITY NAME WITHHELD), I could help you out."
"Really? I do, I mean I live in a suburb but I'm really close. Would you?"
"Sure, sugar, I'd be glad to. It'll be a wild ride, but I'll get you past all your fears. I'll text you my address and come over this Saturday at 1pm."
"Uh, do I have to pay?"
"First time is free. If you like it, we can come to an arrangement," I said smiling, seeing the money roll in from yet another "sissy student".
"I'll be there! Thank you! Thank you so much! This is amazing!!"
"Looking forward to it, sweetie. Bye bye!"
It was about time for dinner so I put the Help Line on to auto-answer. I'd recorded a few sexy monologues of myself and sissies usually called to hear those and cum in their panties.
My new roommate, Charlotte was in the living room with the mover and lots of boxes.
"Where should I put this?" asked the mover. It actually was one of my boxes. I'd only moved in two days earlier.
"Oh, you can put that in Annie's Room," directed Charlotte. We'd been friends for years and often 'more than friends' so rooming together had all sorts of exciting possibilities.
After the mover headed upstairs with my box, I came over and gave Charlotte a little pat on the tush. She looked amazing in her leggings and crop top, her white jog bra peeking out trying to contain her large breasts.
"I've got another sissy client on Saturday," I mentioned as began to get nosy with her stuff. I saw a stack of DVDs hand-labeled as BJs finished by swallowing every drop voluntarily. We had similar tastes. "You up for helping out?"
"Sure, I could use the distraction and 'exercise'. Bianca will be here too but she's always up for it," she purred back. I was tempted to start feeling her up right there but the movers were on the clock. The one came back down from upstairs, nodding to me with a smile before heading to the truck outside. He was a finely built younger man with mahogany skin.
"I wonder if he'd like to play. Having a real cock around has all sorts of uses..." I mumbled to myself.
When he came back in with another box, Charlotte stopped him. "Hey, Carl, do you want to come over Saturday afternoon for a lot of kinky group sex?" I think that was the first time I'd seen a black man blanche a little out of shock but he clearly warmed up to the idea quickly. I saw his pants shift and he was a blessed man.
"I'd love to. Just you... two?"
"And another guy. You okay with that?"
"Yeah, I like it all."
"You're in. Show up at..." she began and looked at me.
"2pm" I finished. Carl certainly had pep in his step for the rest of the move-in.
Later, Charlotte and I were cooking dinner and discussing plans for Saturday.
"A total newbie? Starting him with dress up, I assume, but how far do you think he'll go? Pegging?"
"When being dressed up by a pair of Lesbians, I think he'd love to be on the receiving end."
"Do he tell you any of his Sissy Fantasies?" She strained the pasta and I finished spicing the sauce.
"No, but that can be ice-breaker talk. I put that box of big-sized High Heels in the play bedroom so I think locking him into some of those will make it hard for him to bolt and he'll love it."
Saturday came fast as Charlotte and I worked and put our new house together in order. We went for a run together, got back and showered before the 'new one' was going to show up. Again, I had to resist showering with her but we'd still have been going at it when he arrived. Bianca arrived about 12:45pm and got herself a drink while we dressed. She was wearing some of her 'call my Mistress' leathers.
I selected a fairly flirtatious, deep cut top, a satiny teddy, a short skirt, thigh highs and heels. Charlotte went with a bikini swimsuit and skirt and sandals. At 1pm on the dot, the doorbell rang.
I liked what I saw when I opened the door. He had his eyes cast down (already showing submissive deference) and was a slender young man on the short side. He'd fit into... size L in most women's lingerie and clothing I guessed. He was blushing already.
"Welcome to Annie's Realm, sissy. Tell me your sissy name and you may enter."
He swallowed hard, his eyes sneaking gaping looks at me. "C... Candy."
"Alright Candy, enter and become the girly slut you always dreamed of." Again, he was hesitant but he stepped through. "Take your boy costume off and leave it on the chair there."
He began stripping and only hesitated when he was down to his boxers. His cock was small but very stiff at this point.
"Girls, finish him off!" I say with glee as I close and lock the front door. Biance and Charlotte saunter, cozy up against him and before they can pull his boxers off, he moans and cums.
They wait until he's pumped his full load in his boxers and then carefully take them off of him.
"I'm so sorry, Mistress Annie," he began, very distraught. I waved him to silence.
"Honey, it's understandable to get excited. Let me help you." I quickly put his soft little cock into a small chastity and clicked the lock shut.
"Wha.. I don't..." he began to babble.
"It's for your own good, sweetie. This will keep you focused and obedient or you'll wear that home." I went and carefully picked up his boxers. "Now, because you were so 'eager' we're jumping ahead a little. Lesson one will be Eating Your Own Cum."
His eyes grew wide but Bianca and Charlotte laid it on thick and kept rubbing their curves against his body, telling him how sexy it was for guys to eat cum and how much it would turn them on.
Surprisingly, Candy got on board pretty quickly and licked and sucked his whole load out of the boxers.
"Good girl! I'm impressed. Next time it will be out of panties, or straight from the cock!"
"On to play dress up!" I announced, dropping his wet boxers on his clothes pile which Bianca would quietly hide later. I led Candy up to the play bedroom where I'd laid out several panties, stockings, the high heels, bras, corsets and a bustier.
"What looks most girly and sexy to you, Candy?"
She pointed to pink satin panties so I helped her step into them, pulling them up slowly and then snug over her bottom and caged clit. (I always starting thinking of sissies as she by this point). I suggested a matching satin bra and gave him some large, heavy false breasts to place in them. Usually I'd use adhesive to her chest but we'd skipped all the hair removal. Another time perhaps.
Candy couldn't wait to get all girly dressed, putting on thigh highs and the high heels. She began to prance around and gaze at herself in the mirror. Her body had a lot of 'natural talent' which if guided and shaped meant she could be very girl-like in her body and features. Such potential!
This is when Bianca started taking flash pictures with her phone, uploading them to the cloud.
"Wait! Don't.. Nobody can see me like this!" begged Candy, distraught.
"Don't you think she really wants to be Naughty at Work? teased Charlotte, ignoring Candy.
to be continued?!?
Okay, that's eleven for me. Who can beat that?
