Previous Chapter Back to Content & Review of this story Next Chapter Display the whole story in new window (text only) Previous Story Back to List of Newest Stories Next Story Back to BDSM Library Home

Review This Story || Author: Wrt4ffun

A Lesbian Sissy Story

Chapter 2

                                                                 A Lesbian Sissy Story                                                              

                                                                  part 2

.For the few of you who liked this concept here is Chapter 2.

When the alarm sounded Tommy was still clutching the damp panties that his mom, or more accurately Miss Beverly, had dropped on his face. They still smelled good even though he had spent much of the night sucking at the silky garment and dreaming of pretty ladies. He had spent a restless night because Miss Beverly had warned him that he would be punished for any stains on his sheets. He awoke with a very hard cock.

He carefully touched himself and felt a few shivers but did not want to spoil the moment. It would be nice to cum but he enjoyed the tension even more. Being hard and lustful was a lovely feeling. Not wanting to disobey Miss Beverly he squeezed his balls tightly to quell his lust and left his bed.

He went to his closet to get dressed but found it empty. His dresser was empty as well. The only garments in his room were a pair of pink panties and a little yellow dress hanging on the doorknob. Well, he certainly could not go parading about naked so he stepped into the panties and felt another lovely shiver as the silky texture of the fabric caressed his swollen penis. He slipped into the yellow dress

and looked at himself in the mirror. He rather liked the look. If his hair was longer

he could easily pass for a young girl awaiting the development of her breasts.   

Remembering his instructions  He brewed a pot of tea, toasted a muffin and spread some strawberry jam on top. Holding it all on a tray he knocked gently at Miss Beverly's door.

"Yes, you may come in."

Tommy entered to find Miss Beverly sitting high in her bed. Her white satin robe was draped about her shoulders but did little to hide the fullness of her ivory breasts nor her outstanding pink nipples. This  was the moment he realized that she would never again be just 'Mom.' Had he really once been fed from those devine orbs?

tommy swooned and nearly dropped the tray but suddenly found himself on his knees beside the bed without spilling anything.

The pretty lady was barely able to stifel a giggle but managed a coy smile as she reached for her tea.

"Oh! Tammy, my very sweet girl, you brought muffins too?"

"Put the tray down and give Miss Beverly a kiss."

Tommy noted that he had been renamed and referred to as a girl but he really didn't care as he moved closer to Miss Beverly and felt her full mouth engulf his own. Her deft tongue slid between his lips and licked all around.

Bev broke the kiss, began to sip her tea and completely ignored the boy. Tommy felt both lust and confusion as he watched the pretty lady on the bed finish her breakfast and light a cigarette.

"'Tammy, honey, you look so nice in your new outfit. How about we go shopping soon and get you some more dresses and panties? Maybe I could invite Larissa to come with us. For now, I think the yellow really suits you and I will get you some cute heels to match all your frocks."

"But, these are clothes for girls," said Tammy.

"Yes, sweetie, but they also look very fetching on sissy boys.

"Do you think I am a sissy?"

"I'm quite sure of it darling. You steal my panties, sleep with them and then beg me milk you. It's obvious that you lke your new frock. Just look at how your little pricklet

is making such a tent in your new dress."

"Stand and twirl for me. I want to see how it looks when you move."

Bev reclined on her bed smoking and sipping her tea while she had Tammy model his new outfit. She played a CD by 'Pink' and asked him to dance for her. At first, the boy had been shy but with her encouragement he was eventually vamping and flirting like a very cheap stripper. Bev clapped at his performance and invited him closer.

"Raise your dress, honey, I want to see your girly cock. Just bring it out the leg of our panties. woudn't that feel good?"

"Yes", said Tammy,

he boy scampered to the bedside and beheld Miss Beverly's perky breasts as well as her pretty feet.

They were smooth and white with newly painted nails of crimson and little flecks of gold embedded in the polish.  His penis jumped straight out from beneath his short dress with drop of precum right on the tip. Miss Beverly took a firm hold of his shaft and squeezed tightly.

{I'ts a pity it is so small. Tammy. Let's see what we can do about that."

Now, Tammy was not at all under endowed for a boy his age but Bev thought it would be best if he believed it in order to make his transition into the sissy lifestyle

easier. She waved her pretty foot before him and then brought it beneath his dress. She ran her soft sole along his hard dick until he began to gasp and thrust forward.

Knowing that Tammy was on the edge Beverly pulled her foot away.

"Wow! That did make difference, didn't it?"

"That's really not bad for a girl your age."

"You really like Miss Bev's tootsies don't you? But, honeybun, I have been wondering whose toes were more tasty. Mine or Larissa's?'

"I think you would be the best judge of that. Don"t you?"

Tammy blushed but could not form an answer. He merely walked toward the foot of the bed where ten colorful and sensual toes were waving in the air. His eyes grew wide and his cock was now standing so firm that Bev wondered if she had gone too far. She did feel some pride that she could have such an effect on him but she was not some incestuous pervert. She was a perfectly good mother that just wanted to have sex with her best friends daughter and help her son to become the sissy he was clearly meant to be. The boy, however, would require some attention and education for things to go properly. She would propose a trade. She would leave Tammy in the care of Celeste and gain her permission to take Larissa on her next business trip.

Tammy knelt at the foot of the bed and noticed that Miss Bev's feet became prettier the closer he got. He leaned forward and found the aroma intoxicating.

He tasted one toe and then another. He took them one by one between his lips. He began to love the sensation as they wiggled within his mouth.

Bev  lit another cigarette and began gently rubbing the fabric of the satin panties that covered her very moist pussy.

You're a good girl,Tammy, now lick between my toes."

With dreamy thoughts of Celeste and Larissa Bev brought herself to a satisfying climax. She rested for a moment then sat up to see that Tammy still had his mouth on her feet. He was most ardent as he placed soft kisses all over them.

""Stay right there, honey buns, I have a special treat for you."

Beverly rose to pinch the tip of Tammy's straining penis and then leap from her bed leaving the needy prick waving in the air. She returned wearing her new high heeled mules. They were red with five inch heels and a wide leather vamp that left her toes exposed. She used a gentle hand to guide Tammy into postion. She stood before the kneeling boy, tossed her hair and then slowly removed her panties.

"They're very wet. Just the way you like them."

"Taste them and make yourself come for Miss Beverly."

"Use your hand, honey, I want to see your pearly drops all over my new shoes."

Tommy was in awe. He took the panties and held them to his face while the gorgeous vision above him did a little shimmy dance that caused her breasts to bounce. It did not take long before his pearly drops were splattered all over Bev's new shoes. They both took a moment to enjoy the sight as his cream slid slowly over the smooth leather of Bev's shoes and onto her painted toes. 

:You're just too delicious,Tammy. I think we have had a good bonding as Mistress and servant but for the fun to continue you must agree to be my sissy maid and dress like a girl for me. Do you see what fun good girls get to have?"

"Yes, Mom, that was really nice."

Bev gave the boy a sharp slap on his face.


"Who am I darling?"

""Miss Beverly?"

"Yes, that's right and who are you?"

""I'm Tammy."

"That's my good girl."

"Since you like ladies panties so much  I think we should start at Victorias Secret. some sexy panties and pretty dresses would make you a most desirable sissy. The boys will go crazy for you. Wouldn't you like that?"

"But, I don't like boys", said Tammy.

"I want to be a girl so I can be like you and Celeste. I saw you together once and it was beautiful."

"Bev had been unaware that Tammy knew of her intimate relationship with Celeste but thus far her plan was showing great promise.

"Tammy, baby, I have make a trip next week and I was thinking that I could have Celeste look out for you. You would have to stay in her house, do everthing she tells you and continue to dress as a girl. Could you do that for me sweetums?"

"Er, I, Sure. I  like Celeste a lot."

""Oh really, and what do you like so much?"

""She's  hot. I love her clothes and her  legs and sexy shoes. She has a really nice butt too. Do you think she would let me kiss it?"

""Oooo, you naughty sissy, Celeste is going to love you but we'll have you get you

properly trained so that you can be of use to her. She can be very impatient, domineering, and a bit arrogant as well."

"Are you sure you want this Tammy?"

Tammy remembered a time when he was home last summer. He had dropped some chips in the kitchen and was on his knees picking them up when Celeste strode in to get another bottle of wine. She had been wearing a short black dress with matching five inch pumps.

The woman had stepped right on his hand and just stood there looking down on him with an amused smile. He did not recall any pain because from his lowly position he could see her lacy stocking tops. The lady quickly found the wine while the boy remained on his knees collecting chips. As she left Celeste stopped again and slowly brought the toe of her pump between his legs and gave a few taps while licking her lips. Tammy did recall that he could not take his gaze from her superior smile.

:'Better go upstairs, boy, unless you want to make a bigger mess," she said with a chuckle.

He had done just that. Filching a pair of Bev's panties Tammy had jerked off twice with them as he relived the incident with Celeste. Arrogant, bitchy and beautiful?

That didn't seem so bad if he could stay with Celeste.

The trip to the mall was exciting for both of them. Bev drove with her skirt pulled high feeling very confident and sexual as she observed the bulge in the tiny shorts that Tammy wore. She led him through the mall and he stood by quietly as she purchased several panties in just his size. Skirts and dresses required some fitting but the cute sales girl seemed to understand and gave a wink as she led them to where Tammy could try on his new frocks. Bev paid for five dresses on her card

and along with her receipt was a phone number and the name Melissa. Bev smiled sweetly and promised she would call. The last stop was at a shoe boutique where a slightly plump but pretty lady was very amused to fit Tammy with several pairs of heels and frilly socks. Bev liked the woman's attitude and secured her contact number as well.

Later that night Bev had him model each of his new dresses and dance for her.

When the final CD ended Bev ordered him to bed. He begged to stay with her and she relented with some conditions.Tammy agreed and stood by the bed as Miss Beverly took a lace from her running shoes and tied it tightly about his balls. She then found a ribbon and wrapped his cock until it became very small. Only then was allowed into her bed.


"Now, there will be no leaky girly cream all over my sheets."

"Good girls don't go around leaking in their panties nor pretty dresses."

"You like your pretty dresses don't you, Tammy?"

"Yes, Miss, they feel good.'

'I thought they would, now, let's go to sleep."




Review This Story || Author: Wrt4ffun
Previous Chapter Back to Content & Review of this story Next Chapter Display the whole story in new window (text only) Previous Story Back to List of Newest Stories Next Story Back to BDSM Library Home