Sissy's Sleepover, Pt. 03

Dear Reader,

Earlier in this story, sissy Jamie's mother planned a sleepover and invited three attractive girls. He was nervous about revealing his feminine persona but the young ladies turned out to be very warm and supportive. When it was time for bed, Pamela chose to sleep with him.

Sincerely,

Whippet

--

"Pamela," said Mother. "You and Jamie can use my bedroom tonight. It's larger and the en suite bathroom will give you privacy."

"Thank you, Mrs. Handley," said Pamela. "That's very thoughtful of you."

Pamela fetched her overnight bag and I showed her into Mother's bedroom.

"It's charming!" she said upon entering. "I love the floral wallpaper and the soft lighting."

Then she added, "Jamie, I'm going in the bathroom to get ready for bed."

I was already dressed for bed. The girls had given me a beautiful peignoir set which I had been wearing all evening. I loved the gown's sheer mesh bodice and crocheted floral appliques. Its matching robe had billowy lace sleeves with dainty embroidery. The satiny fabric against my skin made me feel so wonderfully feminine!

When Pamela emerged from the bathroom she was wearing a G-string and an open cup brassiere. I nearly fainted!

She slowly pirouetted for my benefit. I gaped at her voluptuous bosom and full round derriere. Her breasts were milky white and the nipples were erect. She smiled at me invitingly.

I was too shy to approach her or even to speak. Her raw sexuality overwhelmed me and I began shaking.

"Shall we get in bed, Jamie?" she asked warmly.

I was terrified and didn't know what to do.

When Pamela saw the fear in my eyes, she took my trembling hands into her soft grasp.

"What's wrong, Jamie? Do I frighten you?"

I nodded my head and whimpered, "I want my Mommy."

"Oh, you poor scared sissy. Of course you want your Mother. I'll get her."

--

I was still standing next to the bed when Pamela returned with Mother.

"Jamie," said Mother. "Pamela tells me that you're afraid of her. Is that what's wrong, Sweetie Pie?"

"Yes, Mommy," I said as I began sobbing.

Mother sat on the bed and drew me onto her lap. Then she dried my tears with a tissue and pressed my face to her soft bosom.

"Is it because you're afraid of sex, Honey?"

"Yes Mommy," I admitted bashfully.

"Jamie," she said. "Pamela is a nice girl and she wants to help you when you get a stiffy, Sweetie. Just like Mommy does. Isn't that right, Pamela?"

"That's right, I want to help you, Jamie," said Pamela warmly.

Then Mother said, "May I show Pamela how I help you, Honey Boy?"

"Okay, Mommy," I said nervously, "but I don't have a stiffy right now."

"That's alright, Darling," she replied. "You will."

"Pamela will you please turn off the room light and sit with us?" she added.

"Yes, Mrs. Handley," said Pamela.

I felt better already seated on Mother's lap with only soft candlelight illuminating the room.

"Now, Pamela," Mother continued, "Please lift Jamie's pretty nightie while I massage his sissy clitty."

I gasped when Pamela lifted the hem of my gown. No one except Mother had ever done that.

"It's alright, Sweetie. Mommy's here," whispered Mother.

Then Mother gently touched my little weenie. I was nervous about having Pamela on the bed next to me but when Mother pressed my face to her bosom and massaged my willie I began to relax. Soon I was moaning and my dickie was getting hard.

Mother stroked me a while longer while my passion grew and then said, "Do you like Pamela, Jamie?"

"Yes Mommy. She's nice and she's very pretty," I replied.

"Would you like Pamela to touch your boy clitty, Jamie?"

"I guess it might be alright," I said hesitantly.

"Ask her, Sweetie Pie," said Mother.

"Miss Pamela, would you please touch my clitty?" I parroted.

"Of course, Jamie!" she replied warmly.

Then Mother handed off my willie to Pamela. Her fingers were soft and moist just like Mother's and I loved her gentle touch.

Pamela stroked me just like Mother and then asked, "May I kiss Jamie, Mrs. Handley?"

"Of course, Pamela," said Mother, "Jamie is wonderfully submissive. He'll do whatever you want."

Pamela kissed me deeply. My passion grew as she thrust her tongue through my yielding lips.

Then I heard Mother say, "I'm going to bed now, Jamie. You be good girl and obey Pamela just like you would Mommy. Okay?"

"Yes Mommy," I said. "I'll obey."

I heard the door close as Mother left me alone with Pamela.

--

"Let's get under the sheets, Jamie," said Pamela when Mother had gone.

"Okay Mommy," I said out of habit. "Oops, I mean Miss Pamela!"

"It's alright, Jamie," she said and then asked, "Do you want me to touch your stiffy again or shall we just cuddle?"

"I don't know, Pamela," I replied meekly. "Can you please decide for us?"

"Alright, Sweetie," she cooed. "I think you've had enough excitement for now. Let's cuddle."

"Will you please spoon me, Miss Pamela?" I begged. "That's what Mommy does."

"Of course, Honey. I'll spoon you."

I soon fell asleep in Pamela's tender embrace.

--

I awoke in the morning with a raging boner in my panties. Pamela was awake too and she sensed my need. Apparently she had needs of her own as well.

Pamela gazed calmly into my eyes and said, "You understand about intercourse. Right, Sweetie Pie?"

I nodded nervously.

"Will you let me make love to you, Honey Bunch?" she asked sweetly.

I was frightened of having my little weenie inside Pamela's hungry pussy. So I whimpered, "I want Mommy to be with me."

Pamela fetched Mother again and the two women lay down on either side of me.

"I'm here, Honey Boy," said Mother. "Now be a good girl and let Pamela use your dickie."

"Okay Mommy," I said timidly, "but will you hold my hand, please?"

Mother took my hand into hers as Pamela mounted me.

Then Pamela lowered her moist pussy lips to my throbbing willie and penetrated herself. She began moaning as her slick vagina slid up and down my hard sissy rod. Soon her passion swelled and she began breathing deeply. Then she screamed as a violent orgasm rocked her body.

"That was wonderful, Jamie!" said Pamela excitedly as she slumped onto my chest.

"See, Jamie?" said Mother sweetly. "You gave Pamela an orgasm. Aren't you proud?"

"Oh yes, Mommy!" I replied excitedly.

Then I asked, "Miss Pamela, was I supposed to have an orgasm, too?"

She responded very sweetly, "You're my sissy lover now, Jamie. If you'll be a good little pansy and promise to obey me I'll let you climax in my pussy."

"Did you hear that, Mommy!" I squealed. "I belong to Miss Pamela and she'll let me make cummies inside her!"

"That's wonderful, Darling!" said Mother. "I'm so happy for both of you!"

"Can I cum in your pussy right away, Miss Pamela?" I begged.

"Of course, Sweetie", she said with a smile. "You must wait until I climax before you spurt though."

Pamela mounted me again and my heart flip-flopped with joy when she ravished me for the second time. Before long her passion soared out of control and another powerful orgasm shook her body.

Then she said, "Okay Jamie. It's your turn."

I was the world's happiest pantywaist as I spewed a huge load of sissy cream into Pamela's steamy hoo-ha!

--

That concludes the story of sissy Jamie and his wonderful sleepover. I hope you liked it and that you'll post a comment.