Mommy's Pajama Sissy -- Part 9

Tammy never shared with me all the details of his date with Steve. But it was very clear to me that Tammy had had an amazingly romantic and passionate evening.

But now Steve was gone, having moved to New York, and I could tell My Little Princess missed him, even though they had only been together on one exciting date.  But the last day of school was fast approaching and that was something good to look forward to.

At Tommy's high school, they have a fun tradition where the graduating seniors -- of which Tommy was one -- come to school in their pajamas on the last day of school.  Of course Tommy had never been one to get very involved in school activities.  He never went to football games or pep rallies or things like that. So I wasn't sure if he would even want to participate in Senior PJ Day, as they call it.

Well, he DID want to participate. And he wanted to participate in a very special way.

"Mother," he said to me. "I've been hiding all my girlish feelings from everyone for so long, always pretending to be someone that I'm not.  Well, tomorrow is PJ Day -- and it's the last day of school forever. So I want to go to PJ Day as Tammy.  The real me.  In a nightgown.  And if people don't like it, well fuck 'em!"

Tammy had never used language like that in front of me before.  It showed how strongly he felt about what he wanted to do.  So I gave him my full support.

Senior PJ Day arrived and we both got up extra early.  We took extra time getting Tammy ready for "her" very first appearance at Tommy's high school.  I warned Tammy that people would be shocked and that he would probably get some pretty strong reactions from people.  But Tammy was determined.

We hadn't discussed it before, so I asked Tammy, "So what exactly are you going to wear today.  Which nightgown have you chosen?"

Tammy replied.  "I have a favor to ask. Can I borrow your white night gown and robe set?"                                                                                  "You mean the one with the eyelet and lace trim? And the buttons down the front?  I haven't worn that one in years.  Well, I guess you can borrow it.  But, it's a bit...grown up and...romantic to wear to school."                                                                                                    "I understand. But it's what I want to do." And with that, I dug out the nightgown set from deep in my lingerie drawer.                                                                                           Tammy put it on and he looked absolutely stunning.                                                                               Ten minutes later I was driving him to school.  His hair and make-up were perfect. He wore just a bit of perfume.  As we pulled up to the front of the school, I asked one more time, "Are you sure you want to do this?"                                                                                             

 "I've never been more sure of anything." And off he went to the entrance of the school.

All morning I worried about My Little Princess being at school looking like a bride on her wedding night.  I kept me cell phone with me in case I got a call and needed to rush to school.  But no call ever came.  At 1:00, I drove back to the school to pick up Tammy, as the last day always ended early.

"How did it go?!?!" I asked excitedly as Tammy climbed into the car.

"It was great!" Tammy said with a smile.  And he proceeded to tell me all about his day. 

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."

Mommy's Pajama Sissy -- part 7

 

Tammy was having a magical time at the fancy tea dance, being led on the dance floor by his handsome date, Steve.  Tammy allowed himself to be carried away by the experience, resting his head on Steve's shoulder.  And when Steve leaned in to kiss Tammy, Tammy didn't resist at all.  Deep kisses continued on the dance floor as the band played a slow, romantic song.

"I'm going to miss you when I leave for New York on Monday. Do you think you will be able to visit me?" Steve said.

That question triggered something in Tammy's head that he decided to act on.  "Steve," Tammy whispered in his ear as they danced, "I haven't been completely honest with you."

"Oh, really?" Steve replied, having no idea what he was going to hear next. "Well, now might be a good time to set the record straight. I'm ready. Let me hear it."

"Well," Tammy said softly into his ear. "For one thing, I'm not really 22 years old like I said last night. I'm 18."

"Yikes!" Steve responded with real surprise. "That makes me much older than you. I really shouldn't be dating 18 year old girls. Well, at least you're...legal.  I'm going to need to think about this. But in the meantime, please lay off the champagne.  You shouldn't be drinking."  Tammy agreed.  "Was there something else? Steve asked.

"Well, yes," Tammy started. "This is a bit hard to explain, but I wasn't exactly born this way. I mean, gender-wise.  I haven't always been a girl like this."

"Are you saying that your trans?" Steve whispered back to Tammy. "Wow, that is a surprise. But you're so...feminine. I would never have thought. I suppose you transitioned when you were young.  Wow, there is a lot to learn about you!"

To Steve's credit, he seemed more concerned with Tammy being 18 than the fact that his date was a transwoman.

"It's not exactly like that," Tammy whispered back. "I...I...I," Tammy stammered.

"You what?" Steve prompted, struggling to keep his voice at a whisper.

"Steve, I'm a boy," Tammy explained simply.  Steve went a little pale. 

They retreated back to their table where Steve said, "Look, there is a lot we need to talk about but we can't talk here. I was planning to take you out to dinner later, but maybe we should just go back to my folk's place and talk in private there.  Is that OK with you? Tammy agreed and off they went.

Mommy's Pajama Sissy -- Part 6

When Steve returned from the rest room, I made an excuse that I saw friends across the room that I wanted to talk to.  That gave Steve and Tammy some alone time.  When I returned about 15 minutes later, Steve said that he needed to leave so we said our good-byes and he left.                                                                                                                 "Well?" I said to My Little Princess.                                                                                                              "He asked me out for tomorrow.  And I said yes." Tammy replied with a bit of embarrassment in his voice.  I squealed with delight at the news and gave Tammy a bit hug.  Tammy gave me the details.  Steve's family belongs to a fancy country club just outside of town. There was a "tea dance" scheduled for Sunday -- tomorrow -- afternoon.  Steve would pick up Tammy at 2:00 and head over to the club.                                                                                    "Oh what fun! I think the little black dress we bought yesterday would be perfect.  Don't you agree?" I said.                                                                                                                                                                 "I guess so," Tammy replied uncertainly. "I don't really know about any of this..."                                                                                                                "Oh, don't be nervous. We'll make you the prettiest girl at the dance and you will be full of confidence. But for now, we should get home so you can get a good night's sleep before your big date tomorrow!"  And so we left. 

Sunday morning was very busy with getting Tammy ready for his big date with Steve. After breakfast, we spent all morning making Tammy look his prettiest.  We did his hair and his make-up.  He wore some of the new underwear we had bought at the mall just two days ago.  He slipped on his pretty new black dress, its straps accentuating Tammy's delicate shoulders, its neckline plunging intriguingly low.  I lent Tammy a chucky necklace and some strappy black sandals that went well with his outfit.                                                                                     "Mother," Tammy asked as he was admiring his own reflection in the mirror, "Don't you think I need to be honest with Steve about....everything? I mean, it doesn't seem very nice to be tricking him this way."                                                                                                                                               "Well," Mother replied, "I think you will need to figure out what needs to be said and when over time.  Don't worry about it too much right now.  Just try to have a good time and enjoy the experience. But if you decide at some point that you want to give Steve the truth, well that will be up to you.  But be thoughtful -- actions have consequences."                                                                                        Tammy was still thinking about his mother's advice when, at 2:00 sharp, Steve pulled up to the house in his BMW and off they went.                                                                                                                       Well, Tammy had never been to a fancy country club, let alone a tea dance, even as Tommy.  The experience was thrilling for him.  The valet parked Steve's car and Tammy entered on Steve's arm.  Waiters were passing trays of champagne and Tammy took one and drank it quickly.  Steven found a little table near the window where they sat and chatted. Older couples -- friends of Steve's parents, Tammy figured out -- would stop their to say hello to Steve. Each time Steve would proudly introduce Tammy as "his friend."  Everyone was friendly and polite.

When the jazz ensemble started playing again after a break, Steve asked Tammy to dance, and Tammy agreed. Tammy was really starting to relax, having had three glasses of champagne by this point in the afternoon.  "Why did they call it a tea dance if all they served was champagne?" he wondered to himself, as Steve led him to the dance floor and wrapped his arms around his pretty date.