Mommy's Pajama Sissy -- Part 8

When Tammy and Steve arrived at Steve's parents' home, Steve quickly poured himself a stiff drink.  They had already started having a conversation about exactly who Tammy was and Steve was beginning to come to terms with the fact that the beautiful girl he had been French kissing on the dance floor wasn't really a girl at all.

But Steve wasn't angry or upset.  He really mostly seemed confused and conflicted.  He had fallen very hard for Tammy and it was a struggle to incorporate this new, shocking information with what his eyes and emotions were saying.

"Do you want me to go?" Tammy asked at one point when Steve seemed to be out of questions and the silence hung heavily in the room.

"I don't know.  I don't think so. Maybe if we just spend a little time here together we can figure out what exactly we are feeling and what we should do next," Steve suggested.

So they sat quietly together on the couch for a few minutes.  Steve broke the silence saying, "God, you even smell fantastic."  That comment broke the tension and Tammy giggled a little.

"Steve," Tammy started, "I think you like me as a girl. And I know I like you. So maybe, just for the rest of the evening, we could both go on pretending that I'm really a girl."

"But what would your mother say? Do you think she wants this to be happening?  Do you think she wants you, her son, hanging out alone with an older man who, just a few minutes ago, was kissing you on the dance floor?!?"

"I think my mother has the hots for you just as much as I do. If I wasn't here, I bet she would want to be! But I'm guessing you have that effect on girls' mothers," Tammy offered. "So no. I don't think my mother would have any problem with me being here with you tonight. I think she would be happy that I've having this sort of experience with such a nice and handsome man."

Steve didn't have an answer to that. So Tammy continued, "So, if I really was your girlfriend, what would we be doing right now?"

"Making out, I guess. Is that what you want to do?" Steve asked.

"Yes!" Tammy breathed as he wrapped his arms around Steve's strong neck and kissed him hard.  And Steve kissed him back. Steve pushed Tammy down onto the couch and climbed on top of him.  Their kissing and their breathing became harder.  As did something in Steve's pants.

"If I was really your girlfriend, what would you want me to do now?" Tammy whispered.

"I'd want you to pull down my zipper and take out my dick and start to stroke it," Steve replied. And that's what Tammy did.  Tammy was amazed by how huge Steve's cock was -- many times bigger than his own little one.  And it seemed to grow bigger with each gentle stroke.

"May I put it in my mouth?" Tammy asked.  Steve could only nod.  Tammy kissed the end of Steve's rock hard dick, and then licked it, and then pulled it into his mouth.  Steve's eyes were closed and he was making quiet moaning sounds so Tammy figured he was doing it right.  "Oh that feels so good," Steve moaned.  "So good."

After playing with Steve's dick in his mouth for about 10 minutes, Tammy said, "I want you to make love to me. Treat me like a real girl and fuck me.  Please."

"Let's go upstairs to my bedroom," Steve replied.

When they got there, Steve stripped naked. "Are you going to get undressed?" Steve asked.

"Oh, no. I don't want to be naked. I need to be wearing girl's clothes to feel like a girl," Tammy explained. "Give me a minute." And Tammy exited Steve's bedroom.  A moment later, Tammy returned wearing a black satin and lace nightgown. "How's this?" Tammy asked with a smile as he twirled in front of Steve.

""Did you take that from my mother's lingerie drawer?!" Steve asked with some distress.  Tammy nodded yes with an enormous smile on his face. "Oh, God, I'm going to be in therapy for years because of you." Under the silky nightgown, Tammy was still wearing his bra and padding, so he had the shape of  a woman and Steve couldn't help but be excited by the image of a sexy woman standing before him. 

"Wow," said Steve, "You look amazing. I am so turned on right now." And with that, the two lovers climbed into bed.  Steve positioned Tammy on his side, with his bottom facing Steve.  Steve lifted the hem of Tammy's nightgown, exposing his soft little bottom.  Steve applied some lubricant and warned Tammy that it might hurts a little since it was his first time. Steve began to gently work his giant, rock hard dick into Tammy's virgin sissy pussy.  With each stroke, Steve's cock penetrated deeper and deeper into Tammy. Soon, Steve's thrusts became harder and quicker, his moaning louder, his grip on his feminine lover tighter. And as Steve came inside of him, Tammy's own little penis also exploded into the soft, silky fabric of the nightgown that was rubbing against him.  

For Tammy, the experience was quite painful -- but also exquisite. Allowing his body to be given over for the pleasure of a real man. To feel a real man plant his hot sticky seed deep inside his body. To surrender completely to the needs of the woman that lived inside of him.  It filled him with a sense of happiness and fulfillment unlike anything he had ever experienced.

As Steve's dick began to soften, he started to withdraw from Tammy's backside. Tammy reached around and grabbed Steve's ass. "No," he said. "Please leave it inside of me for just a bit longer."

As they lay there, still wrapped tightly together, they both fell asleep for a few minutes, both feeling exhausted and content.

When they awoke, Steve kissed Tammy again and said, "I think I need to drive you home now, darling."