With Guidance from Grandma

My grandmother lived in California, so I didn't get to see her much growing up. She would visit once a year to spend a few weeks with her son's family (My dad). It was on one of these visits when my grandmother found out about my lingerie fetish.

I used to borrow my mom's lingerie. I thought I was pretty sneaky, and nobody knew about it, but I would later find out my mother had known almost from the very beginning. I guess I shouldn't have taken the sexiest things she owned! If I wasn't so stupid, I would have realized her best stuff would be the most obvious to be noticed if it were to go missing.

My senior year, my grandmother came to visit and watch me graduate. Being a senior and near the end of school, the seniors were allowed some liberty with excused absences. I decided to take advantage of this unofficial practice on a Friday. My parents had gone to work, and my two brothers were out. Even though my grandmother was in the house, I decided to take the opportunity to slip into some of mom's things and hang out in my room. If my grandmother wasn't visiting, I would normally roam the house like any normal boy to watch television, eat breakfast, or whatever else a typical day entailed, except I would be wearing mom's lingerie.

Quietly I slipped into my parents' bedroom and opened mom's lingerie drawer. I picked my favorite pink nightie that fell about thigh high. For panties I chose a white pair that was all lace.

I had been shaving my legs and groin for a few years. Actually, I kept all my body hair closely shaved. I was skinny and hairless. If only I had breasts, you almost would believe I was a girl. I always thought I would make a good girl, but I also loved my dick. I knew how to make myself feel good and had no desire to lose my "best friend."

With my "booty" in hand, I crept back to my own bedroom. Quickly stripping, I briefly admired my hairless body. Mom agreed to my request for a full-length mirror when I was ten, she knew the real reason I wanted the mirror, and it wasn't whatever long lost excuse I had given her.

I watched my reflection as i slipped on those white lace panties, my cock barely concealed. I was fully erect. I loved how I looked. I was a sissy and loved pretty things. Next, I slipped on the pink teddy. My cock and balls ached for release.

Restricted to my room, I felt like a caged animal. Like any caged animal, I wanted out. The thought of leaving my room dressed in my sexy lingerie with my grandmother in the house excited me even more.

What would my grandmother do if she caught me? I imagined she would make me keep wearing my mother's things all day. Would she humiliate me for wearing girly things? Would she tell my parents or my brothers? I didn't immediately realize it but all of those scenarios were making me more and more horny.

Horny people rarely make the best decisions. I decided to risk going to the bathroom. Since our house wasn't very big, it was hard to sneak around anywhere. It didn't matter, me and my best friend were going to risk it because it was a horny decision.

I quietly opened the door to my bedroom and peeked down the hall towards the kitchen. Unfortunately, my grandmother was sitting at the breakfast bar. The good news was her back was to me. The bad news, I had to walk toward her to get to the bathroom. I was quite certain I could make it without her seeing me. Quite certain...

As I crept out of my room, my heart raced. Halfway there, the floor creaked. I knew the floor creaked but this time it sounded like a siren blaring. My grandmother heard it too. I watched as she started to turn around. I had two choices, sprint for the bathroom or scamper back to my safe space in my room. Guess what I did.

My eyes focused on the bathroom door rather than my grandmother. It seemed an eternity for me to get to the bathroom. Once there, I quickly closed the door. My heart felt like it was going to explode.

"Oh my god, oh my god, OH MY GOD!" My mind screamed. "Did she see me? How am I going to get back to my room?"

I looked around the bathroom to see if there was something I could wear to cover myself. The only option would be the towel hanging next to the sink but it would at best cover just my groin, but my still fully erect cock would be difficult to conceal.

I was so horny! I decided to just masturbate to try to come down off of my sexual high which led the stupid decision that got me into this predicament. Maybe after masturbating I could make a smarter decision. In the mirror, I watched myself stroke my cock. With one hand I hiked up the hem of the teddy, with the other I pulled my cock out of my white lace panties. I quickly brought myself to the edge of orgasm...

Suddenly, there was a knock on the door "Are you okay?" my grandmother asked through the door.

My hand stopped stroking. I stood there wondering what I should do.

"You okay in there honey?" she asked again.

I had only closed the door. I hadn't locked it. If I didn't answer she would open the door and catch me in a worse predicament than just wearing lingerie.

"Uh... yeah..." I felt my cock start to spasm. I tried to contract the muscles as if I were trying stop peeing but that made it worse.

"Do you need anything?"

"Uh..." my cock erupted! "I... I'm okay..." It was all I could do to prevent myself from grunting or moaning.

"Just let me know if I need to do anything for you."

"Okay, grandma... I might be a while though."

"Okay, I'll be here..."

Even though I just shot a huge load in the sink, my cock was still hard. I looked around the bathroom again hoping I overlooked something. My choices were pretty simple though: naked or pink teddy. Either way I was fucked. Grandmother was going to know her grandson was a fucked-up sissy. My cock got harder. Deciding to face the consequences of my actions, I at least tried my best to conceal my erection in my panties. Opening the bathroom door, I peaked out. Not seeing her anywhere, I decided to make a sprint for my bedroom.

Halfway there my grandmother steps out of her bedroom door which is one door down the hall from my room. Our eyes locked and for a split second I freeze in place. There is no doubting it now, I've been caught.

"Oh my..." my grandmother smiled.

Regaining my senses I quickly scamper into my room and gently close the door. I was hyperventilating. I felt dizzy so I sat on my bed. My cock was now rock hard. Let there be no mistake. I was mortified. I never felt so embarrassed in my life. At the same time, I was THRILLED. Goosebumps covered my body and I felt that with just the slightest stimulation I could cum again.

It was at this moment in my life I realized I was fucked up. What kind of guy gets horny wearing lingerie? Even worse, who gets even more excited that his grandmother catches him in the act? As I sat there contemplating the depravity of my mind, there is a gentle knock on my door which makes me jump.

"Brian?"

"Yeah?" I answered reflexively.

I guess she took that as an invitation to open the door. It wasn't, and I had no way to cover myself as she entered. The only thing I could do is place my hand over my groin to attempt to hide my fully erect cock. A normal guy caught in this situation would probably go limp immediately. Me? I was getting more excited by the second.

"Oh!" Grandmother said in mock surprise. She just stood there looking at me. The silence was killing me. What was her response going to be? So far, the only thing she had done is smiled at me in the hallway and now she just stood there. Her eyes scanned me up and down briefly although it felt like an eternity.

When she stepped towards me, I snapped out of my mental paralysis. I looked up at her and all of a sudden I became very afraid. I started shaking and tears filled my eyes.

She sat on the bed next to me, putting her arms around me she pulled me into a warm and gentle hug. "Shhh. It's okay baby. Don't be upset."

Even though all her actions so far had been positive, I couldn't help myself. I burst out crying like a baby. Grandma just sat next to me, holding me affectionately. When I finally stopped crying, she released me but didn't move away.

"You okay now?" she asked when I looked up and our eyes met. I just nodded my head. Knowing she wasn't mad started me on a path to actually being able to breathe normally.

"There is absolutely nothing wrong with you wearing lingerie. It's not for all guys, but there are more than you think. Okay?"

Again, I nodded my head.

"Do your parents know you wear your mom's undies."

"No, ma'am." My voice returned but it was weak and pathetic.

"Okay. Don't worry, I won't tell them. It will be our secret. Okay?"

"Thanks grandma."

The next week and the day before graduation, my grandmother took our family out for dinner. At dinner she gave me a watch for a graduation present. It was one of those watches that was not manly nor feminine. On the back she had it inscribed with "Be Yourself, Love Grandma Lacy."

I smiled knowing she had to be referencing my affinity for wearing lingerie. "Thank you, grandma. It's the perfect gift."

"Time waits for no man... nor woman." She smiled.

I felt my groin flutter with excitement. Was she going to go there now? In front of my family?

We both stood up to hug each other. As we embraced, she whispered "I have something else for you. Shhh." When we broke our embrace, she winked at me and smiled.

I was thankful to be able to sit down and hide my growing erection under the table. Without a doubt, I knew what kind of present it was. One that wouldn't be appropriate to show in front of my family. I was rock hard; my head was swimming.

My grandmother was sitting next to me. She recognized my plight. Her hand patted my thigh under the table. Leaning close she again whispered, "Calm down Brandy."

For the record, my name is Brian. Although she hadn't said a word about our encounter the previous week, grandmother was now purposely making me uncomfortable with her teasing. There was no way I would be able to calm down.

Somehow, I made it through dinner and back home without anybody noticing the constant bulge in my pants. That evening, grandma didn't say anything else to make me uncomfortable. Nevertheless, I stayed hard the entire time wondering what my other present might be. Eventually everyone retired to their rooms.

The next day was Friday. Graduation was going to be at eight o'clock that evening. My parents went to work as normal. One of my brothers no longer lived at home and the other was staying with a friend so grandma could have a room to herself. That morning, I knew I would be alone with my grandmother and I would probably get whatever present she had.

As soon as I heard my parents leave for work, I jumped out of bed. I had on normal pajamas. Well, mom bought silky pajamas for guys, but she would find the most effeminate colors and designs she could. My brothers made fun of me wearing them but at least one of them admitted he liked the feel of the fabric. You would think I would have figured out my mother knew my secret but she never confronted me about her lingerie and I was too embarrassed to discuss it with her.

Back to the moment at hand... I made my way to the kitchen to eat breakfast. That is where I found my grandmother.

"Good morning, grandma."

"Good morning, Brandy." She smiled.

"Why are you calling me Brandy." I said, I felt the heat of embarrassment rising in my neck. Quickly I was in full blush.

"Well, you like to borrow your mom's undies, right?" She smiled.

"Sometimes." I hesitantly admitted.

"Just sometimes?" she asked with a smile.

"Well, maybe a little more..."

"I'm gonna guess you do it every time you are alone, don't you?"

I lowered my head as I confessed "Pretty much, yeah."

"Don't be embarrassed by it. Like I told you. You aren't the only guy to wear panties. I'm glad to feel comfortable enough to admit it to me because I bought a few things for you. First though, you need to go take a shower, make sure you do whatever it is you do to remove any hair you have. When you are done come to my room. I'll be waiting."

As you might expect, my cock ached from that point. She noticed the bulge in my very thin pajama bottoms. She was obvious in looking at it as she said "And don't be playing with that thing while you are cleaning yourself up. I'll tell you when you can do that later."

Did my grandmother just tell me not to masturbate? This can't be real. I was pretty sure I just heard her wrong. "Wh... what?"

"You heard me, don't be playing with your little friend there while you're cleaning yourself up."

"Yes ma'am." I replied in shock.

"Good girl."

My belly fluttered hearing her say "Good girl." I don't think it would be possible for my erection to get any harder than it did right then.

Stunned I headed for the bathroom as directed. My routine for my hair removal is pretty elaborate. I have hair cream remover for some areas, and I shave other areas. It is quite literally a forty-five minute process from beginning to end. My parents often berated me for my long use of the bathroom and shower on my "hair days". Mom gave me less grief than dad. I guess she knew what I was doing. Maybe dad did as well and that is why he often gave me a hard time about it.

Anyway, I applied the cream on those awkward to reach places like my ass and lower back. After waiting a couple minutes, I got into the shower and removed the cream and hair before I shaved my legs and groin area as well as my stomach and chest. When I was done shaving, I exfoliated all the areas where I removed hair which was just about everywhere. I had struggled with ingrown hairs for a while before reading exfoliating will prevent it. After some trial and error over the years, those pesky bumps rarely showed up on my skin.

While I was showering, I didn't hear my grandmother enter the bathroom when she removed the clothes I had brought to wear after my shower. I noticed right away my clothes were gone as I exited the shower. It reminded me of being "trapped" in this very bathroom wearing a pink nighty and white lace panties.

After I dried off, I wrapped the towel around my waist before opening the door.

"Leave the towel in the bathroom." I heard grandma call out.

"Oh my god, oh my god, oh my god!!! She wants me to come to her room naked!" My mind screamed. I was too far gone. I was going to do whatever she said. Maybe if I wasn't the horniest I had ever been in my life, I would have made a different decision. Probably not though. Truth be told, this was my ultimate fantasy coming true. I often dreamed about getting caught wearing mom's lingerie and then being forced to do whatever the person who caught me told me to do or my secret would be revealed to the world. With my hands in front to conceal my full erection, I walked towards my grandmother's room, my head was dizzy with excitement!

When I entered her room, I was stunned for multiple reasons. First, and foremost, grandma was wearing a corset that pushed up her very large breasts but did not cover them. Her hard nipples and large areola were clearly visible. She also wore a garter belt and stocking. Her black lace panties barely covered her completely shaved pussy.

The sight of her made my body tremble. I literally fell to my knees as I felt my orgasm burst to the surface.

"Grandma!" I half yelled half moaned. "I can't stop... ohhhh!"

My cock erupted. Cum flew all over the floor. I never even touched myself, but I was in the middle of the most intense orgasm I had ever experienced. Even grandma was surprised by the intense response my body had to seeing her.

"Oh my." That was grandma's favorite expression when she saw something she really liked. "Oh my, indeed."

When my cock finally stopped shooting, I looked up to see her staring down at me. "I'm so sorry!" I whimpered.

"You should be. I told you not to cum. You aren't allowed to cum until I tell you to."

"I'm sorry. I couldn't stop it."

She crossed the room to sit in a chair by the window. This chair was placed there at my grandmother's request because she liked reading by natural light. Once she sat down, she gestured for me to come to her.

"Bend over and place your chest on my lap."

Unnoticed by me until now, she held a riding crop in one hand. I hadn't noticed because her DD breasts had commanded my entire attention previous to this moment.

As I assumed the position, I reiterated my apology. "I'm sorry, I will clean it up. I won't do it again!"

"All well and good Brandy, but you don't get to escape your transgressions without punishment."

Once I was in position she said, "Ass in the air young lady!" When I pushed my ass higher, I felt the first sting of her crop.

"Ow!" It truly and really hurt. It was worse than any spanking or any other kind of punishment I ever had. The next two strikes were even more painful. Tears rolled down my cheeks.

"Now you know what punishment is like. Don't displease me again."

"Yes ma'am." I sobbed.

"Get that bottle of cream on the dresser. I was prepared for this moment."

I retrieved the jar, handing it to her.

"Assume the position." This time when I lay my chest on her lap, I felt coolness on my ass as she applied the cream. "This will take the sting out of it."

She applied the cream liberally and took her time rubbing it into my ass. I started to enjoy her touch. The pain began to subside. When it did, my excitement began to grow. This did not go unnoticed.

As she continued to rub my ass, I felt a finger slide between my ass cheeks, her finger gently crossed over anal opening. It felt fantastic.

"Ohh... mmm" I said in surprise and then pleasure.

"My little sissy likes her ass played with, doesn't she?"

"Oh yes. It feels so good."

This continued for several minutes. She never attempted to penetrate; she was just massaging every inch of my ass. When the cream had been completely rubbed into my skin, she stopped.

"Time for your other gifts."

Taking that as my cue, I eased myself off of her lap. I knelt in front of her without being told. Noticing my gesture of submission she smiled. She didn't immediately stand up. Instead, she just stared at me.

"So, Brandy, I take it you have done some reading or more than likely watched some porn on the internet related to being submissive. Am I correct?"

"Yes, ma'am."

"Look at my little Brandy. So eager to serve. We have so much to discuss!" She smiled at me before lifting her bare foot towards my head. I had read how foot fetish often played a part in the submissive role. Without hesitation, I opened my mouth, offering up myself to further subservience and humiliation. My cock began to grow hard again. "Such a naughty boy. Go ahead, suck Mistress Grandma's toes for her."

"Yes, Mistress Grandma." I said obediently before I leaned forward to lick and suck her delicate feet. Luckily she took very good care of her feet. At sixty years old she still looked very sexy and desirable, especially to a horny eighteen-year-old virgin.

"I must say, I didn't quite expect this so soon. I figured you would be easy to control but your desire to jump immediately into such a submissive role is a pleasant surprise. Since you're my granddaughter, I will take it easy on you... at first. But you may be getting into something you didn't bargain for."

"I'm yours to do with as you please." I said with conviction. She may not have believed me, but I had dreamed about being dominated by a woman from the moment I was exposed to that concept. I was willing to do anything she asked. Over the next few years, she would push me to my limit, but she never broke me.

"Oh child. So sure of yourself. I've broken men tougher than you. They all thought they could handle me. I hope you have a lot of your grandfather's DNA in you. He was the only one I never doubted could take whatever I dished out."