Pandora's Box

"You looked good all dressed up tonight," she said as she stroked my cock gently.

"Thank you. You did too."

"Did you like being all pretty tonight?"

She stroked my cock a little faster and popped her hand off the head of my penis as she squeezed it a little tighter.

"Yes," I gasped as I caught my breath and she held tight to the base of my now, erect and sensitive cock, teasing my shaft and head with her free hand.

"Did you want to fuck that guy?"

"No."

"No? Are you sure? You looked like you wanted to fuck him?"

"No," I gasped again as she began to massage my balls between strokes. One hand went up and down the length of my cock and the other rolled my balls between the palm of her hand and her fingers.

"Did you want to blow him?"

She looked me directly in the eyes as she asked, then leaned forward and blew her warm breath over the head of my cock.

"Well, did you?"

"A little, maybe."

"Don't lie to me," she said and licked me from base to head. "You wanted to blow him, say it."

"Okay, I did." I said the words between breaths. "Alisa, you're killing me here."

"Say it."

She teased me with her words as her hands continued to tease my cock. "Tell me you wanted to blow him. Tell me you wanted his cock in your mouth."

Her hands continued to glide up and down my cock. She stopped for a second and teased her fingers over the head of my erection, then scratched her nails up and down my shaft again and again. Chills ran up my spine and I bucked up into her hands for more.

"Please, Alisa, stop teasing."

"Say it."

"I wanted to blow that guy. I wanted his cock in my mouth. Happy now?"

I bucked up again and reached for her waist.

"No, no, no. No touching for you. Put your hands down."

I looked at her. She'd never acted like this before. I had no idea what had come over her, but I'd be lying if I said it wasn't a major turn on for me.

In just a few seconds, she switched positions and was straddling my chest with her ass toward my face. I couldn't believe what she was doing to me. Hell, I couldn't believe anything she was doing. It wasn't at all like her to take charge and talk dirty.

"Well, you're going to have to make do with me. If you bring me to orgasm with your mouth, I'll let you come. If not, I'm going to edge you over and over again before I decide if I'm going to allow you to come tonight."

"Jesus, what has gotten into you tonight?"

"Does it matter?"

"No. No, it doesn't."

"Good, now stop talking and put that mouth and tongue of yours to work."

With that, she pushed back, and sat on my face.

Her scent was so strong and musky. I could tell how turned on she was by both her scent and the wetness that coated my face as she leaned back and covered half my face with her ass and pussy. My nose was literally sliding between the cheeks of her ass as my tongue fought to reach her clit and she rocked just far enough forward to keep it out of my reach.

I licked and sucked whatever part of her I could reach as she teased me by lifting just out of reach of my mouth and then sitting back down, only to pull away a few seconds later. All the while, she was bringing me to the edge and stopping.

"Oh, fuck...fuck...fuck...:" I cried out as her skilled hands had me so close and then released me before I could fully let go.

"Not yet," she teased and sat back down on my face. "Not until you give me a little pleasure."

"Back up a little," I begged.

"Too easy," she said and began to stroke my cock again as she squeezed and released my ball sac, causing me to cry out again.

"Fuck! Oh God, please."

I stuck my tongue out and lifted my head high enough that I was able to lick at her pussy several times before she gave a little moan. Then, she sat back and allowed me to enjoy her fully. I suckled her labia, licked her slit, dived deeper between her lips, and stuck my tongue into her hole. She was so wet, so salty and tangy, I loved the taste of her pussy. I ate her ass and pussy until she came. As a bonus, before she fully recovered, I played with her puckered little hole before sticking my tongue into it and tongue fucking her ass.

"Ohh....yeah...yes...there...yes..." she cried out and wiggled her ass on my face as I pushed my tongue into her as far as I could.

True to her word, she worked me over and over before allowing me release. When I came, she scooped up some of my cum, lifted her ass from my mouth and fed it to me.

All in all, it was an amazing night.

I couldn't believe it was almost a full year since I dressed up and Alisa and I went out that night. Now, some of those same thoughts, feelings, and needs seemed to rush up on me and I needed to address them soon. There was a burning desire coursing through my blood. An overwhelming thought that wouldn't leave my head and a demanding need that wouldn't leave my body.

It wasn't only the idea of the clothes and of dressing feminine again. I'd actually wanted to place an ad for a hookup. I grabbed my phone from the bed and opened on the ad with every intention of deleting it. I read it over and over again.

Male sub/bottom on LBI, NJ. Looking for some dominant male company. I like to dress up and look pretty. Let me know if you're out there and looking for what I have to offer.

Then I laughed at myself. What were the odds that someone was on the island and interested in what I was offering? Less than slim to none came to mind. I tossed the phone down, but I didn't delete the ad. I decided to wait until I spoke with Alisa. Then, I did exactly what I knew I would do since earlier this morning.

I found myself in front of the dresser and rifling through Alisa's things. Before I knew it, I was standing, staring in the large master bath mirror, dressed in her light blue lacy bra and pantie set. I smiled at the idea that the color set off the blue in my eyes. How fucked up am I?

My answer to that came when I walked into the master closet separating the bathroom and the bedroom and started looking through her clothes to see what would fit. Most of her summerware were shorts and capris. Those would not fit me at all. But she did bring a few summer dresses. One by one, I sorted through them. Finally, I found a tropical colored wrap dress that might fit. It would be short on me since I was 5' 11" and about five inches taller than Alisa, but I didn't care.

My body's muscular, but I'm thin waisted and built more like a runner or biker than a bodybuilder. When I put the dress on, I looked at myself in the mirror. I had to loosen the belt a few times before I got it to fit my waist and leave just enough of a V neck to meet my needs. There was no way I was going to be able to wear any of her sandals, so I found my white flip flops and wore them.

I decided it wouldn't hurt if I wore it around the house. No one could see in and if they did, they wouldn't think twice about it. Just some tall lady with short, wavy blonde hair, walking around in a pretty tropical dress.

I picked up my phone and nervously checked to see if I had any messages. Nothing. I was disappointed and relieved at the same time. I wanted her to message me back so we could talk, but at the same time, I wasn't sure what I was going to say.

Making my way downstairs, I realized that I was pretty hungry. I put on some music, opened a beer and pulled out the leftovers. I made a salad and tossed the seafood pasta into the microwave for a few minutes. I was eating my salad and picking a shrimp from my pasta when my phone binged. I practically jumped out of my chair in excitement.

"Hey babe...how was your day?" It was Alisa texting.

"Great beach day. How was yours?"

"Not that good. Everybody thinks the coffers are overflowing and I get to tell them, it isn't so. I swear they think the university has unlimited funds."

"Well, you do get a lot of generous donations. LOL"

"Yeah, and we also get a lot of costly repair and upkeep charges, not to mention a huge payroll that is due every two weeks. They seem to conveniently forget what they make and the bonus monies that were given out at the end of year last term."

"Of course they do."

"I'm going to grab something to eat with the Dean and then head back to the house. What's your plan for dinner?"

"Salad, leftover pasta, beer...ice cream!!"

"LOL..enjoy!"

"You too."

"Xo."

"Babe, before you go, I need to talk. Can we chat?

I didn't need to text another word. My phone rang a second after I hit send.

"What's up? Are you okay?"

"Yeah. I'm fine," I hesitated.

"You don't sound fine. Tell me."

"I'm sitting here, eating dinner, wearing your clothes."

"Okay. And..."

"And, I'm feeling the need for more than that."

"And, you're calling to let me know or to have a discussion?"

"Whichever I need to do. You know I'd never do anything you weren't okay with me doing."

"What is it you want to do?"

I could hear the concern in her voice. I had to tell her the truth, but I was afraid she'd be hurt, or worse, disappointed in me.

"I wrote a personal ad for craig's list. I've been thinking about posting it."

"Thinking about, wanted to or want to?"

"Still want to."

"Will you share it with me?"

"Yes. Definitely. It says, Male sub/bottom in LBI, NJ. Looking for some dominant male company. I like to dress up and look pretty. Let me know if you're out there and looking for what I have to offer."

There was silence between us for several seconds.

"I have to ask, is there any particular reason for you feeling this way right now? I know there's not always a reason, but a lot has changed for you, for us. I'm wondering if you think it's related."

"It might be. I've been thinking about that too. I think I'm feeling a little off my game since the job thing. I feel like I need to allow myself to experience my submissiveness more freely. I want to submit, give in to someone else's control, and be dommed. I don't want to hurt you, but I really need this and it's something that we can't share together in the way I need right now."

Again, there was silence. Then I heard her take a deep breath and leave out a long sigh.

"Please, please, please...be careful. If you decide to post it and if you do get a reply, no matter what time, you call me and tell me what your plan is and text me the info."

"I love you, babe. More than you know."

"Ditto. Please be careful."

"I will. I promise. Are you sure you're okay with this?"

"You know how I feel. Text me the info. Send me the contact number you get and the meet address. Send a pic of the place or the person if you can." She laughed as she heard me groan. "Babe, keep your phone with you and on at all times. It would help if you could message me once or twice and let me know you're okay. Otherwise, you know the agreed upon rules."

"Safety first. Condoms, condoms, condoms."

"Well, maybe not three condoms!"

I smiled. "I love you. Anything else you want or need to know?"

"Just one more thing..."

"What's that?"

"Which of my outfits are you wearing?"

I laughed.

"Your tropical looking dress and some really nice undies that will never fit you right again."

"No doubt my expensive ones."

"No doubt."

"The Dean's calling me. I have to go. Be careful. Be safe. Call me later."

"I will. You too. Love you."

"Love you too. Bye."

We no sooner said goodbye then I hit post on my ad and closed my eyes, hoping for a reply.

I stayed in the dress until after dinner then I ran up and changed. I made sure to hang the dress back neatly and hoped nothing was stretched or out of place. Not that I thought Alisa would care about the dress. I was about to change out of the bra and panties when I decided not to. I pulled my cotton t-shirt and shorts over them and went back down stairs.

I ended up watching a movie on one of the pay for view channels and went to bed early. I checked the ad once before falling asleep and then I didn't think about it again. In fact, I completely forgot about it the next day. Not really, but I tried to focus on other things.

It wasn't until I was on the beach, late in the afternoon, that my phone started buzzing.

Private Message: Very interested, extremely private, highly dominant male, wanting to play with pretty boy/bottom. Tonight, ten o'clock, Loveladies. Message me back if still interested.

"Fuck!"

I was so excited and shocked to get a reply that I said that much louder than I expected to. I looked around to make sure no one heard me. Thankfully, everyone was doing their own thing and not paying attention to me. Now what was I going to do?

My thumbs hovered over my phone as my brain tried to form a response. There was too much nervous energy coursing through me. I couldn't concentrate. I sat there and watched the waves hit the shore as I told myself to breathe in and exhale.

When I calmed myself down, I thought about what I wanted to say. It took me a few minutes to put it together coherently. I told myself to be concise. Don't give too much info. Ask to change the time and see how he responds. I was always aware that there was a chance of someone playing games online or not being who you thought they were. It was difficult to really be sure about anything in a situation like this. I was more aware in that moment, than ever before, of why Alisa was afraid for me.

Well, here goes nothing. Let's see how he responds, I thought to myself as I began to type.

Private Message: Dear very interested, extremely private, highly dominant male wanting to play...Yes, still interested. Nine would be better. Are you able to change the time?

Private Message: Yes, I am "able" to change the time, but I won't. We both know that if you're able to meet at nine, you're able to meet at ten. Don't test me sub. I'm real, very real as you will see tonight. And, I'm not playing with you if that's what you think. At least I'm not playing with you, yet. Attached is the address, see you at TEN.

"Shit!" I laughed to myself.

I was kind of turned on by his answer. I liked that he saw through my ploy and read it for what it was. I was even more excited by the dominant nature of his comment. I read it again...Don't test me sub. I'm real, very real as you will see tonight.

"Shit, gotta love that."

Private Message: See you at ten.

Private Message: That's better. Limits?

Private Message: Not many.

Private Message: Send me your "not many." And your safe word.

Even writing it made me feel more submissive than I had in a long time. I could feel my neck and shoulders relax. I'd missed that feeling, that unique sense of calm that came over me in a D/s situation. Ten o'clock couldn't arrive fast enough.

As always, and as promised, I forwarded his messages to Alisa with all of the known details.

************

I watched as time seemed not to move. Why did it seem like fifteen minutes was so much longer when you were waiting for something.

When I came back from the beach, I took a quick shower outside to get the sand and lotion off me before going inside. I decided to make a light dinner before I went up to take a real shower, prep, and get ready for tonight. It had been so long since I went out in full dress that I wasn't sure how long it would take me to get ready.

After dinner, it was still too early to get ready, so I cleaned up the dishes and had a beer while I relaxed and watched the news. My mind started to wonder what the night would hold. I found myself imagining what he might look like. I decided to message him and see if he would share.

Private Message: Thought you might like to know in advance: Athletic build, pretty fit, runner type. 5' 11" weigh about 185. Blonde with blue eyes.

It took about ten minutes before he messaged me back. It wasn't what I had hoped for at all. But I did find it arousing.

Private Message: Nice. Thanks. See you at ten.

I had to give it to him, he was making things both interesting and exciting. His simple decision not to give me any info on his looks excited me. In my mind, he was already having a dominant influence over me. I could feel things begin to change. My mind began to go to that place of acceptance and I began to feel a sense of yielding throughout my mind and body. It was like I was consciously giving into the sense of "what will be, will be."

I felt different already, psychologically and physically. I was loving it and I hadn't even seen him.

I decided to wear the same outfit I'd tried on yesterday. It looked good on me and it made me feel attractive and maybe even a little sexy. Which were two things I hadn't felt in a while.

Finally, I couldn't think about it any longer. I had to keep myself busy, so I went up and began to set out my clothes. I took a nice long, hot shower. I lathered my face and shaved while under the hot shower spray. As I began to shower, I went to wash my cock and cursed myself for not having the courage to have the laser treatment all over. For some reason, having my cock and balls done was a little terrifying to me at the time. So, more lather and several more minutes were spent shaving not only my cock and balls, but my butt crack too.

I dried my hair and left some waves in it, using Alisa's round brush. Then, I borrowed a little of her pink blush and lip shine. I didn't need to wear full makeup because the sun had colored my skin naturally. Plus, I never really liked using the stuff. But tonight, I wanted to add a softness to my look.

Private Message: Leaving now. Should arrive in 15-20 minutes. Still on?

He responded immediately.

Private Message: Definitely. Enter through the side gate, deck stairs on the side of the house. See you then.

I grabbed my cell phone and my keys and was out the door. I opened the sun roof and turned on some music for the ride. It was the perfect end of summer beach night. The sky was dark, clear, and full of stars. The moon was close to being a full moon and really bright in the night sky.

The weather was perfect and there was a cool breeze coming in off the water. As I headed north on Long Beach Boulevard, I passed through several of the beach towns, each with its own charm. Over the years, I've vacationed in each town at least once, some, several times. I loved them all, but as our income increased, so did the cost of our summer rental.

The address he gave was a Loveladies address. I couldn't wait to see what his place looked like. Most of the homes in that area were either historic older beach houses or huge reno's.

I watched the house numbers as I entered Loveladies. As I got closer to the address he sent, the homes were getting larger and larger. He was on the beach side of the island. Finally, I saw the number listed in his message and pulled into the paved drive. There was a huge sculpted seagull in the center of the drive. I wasn't expecting that and was glad I didn't drive into it.

I quickly sent Alisa a text with the address and a pic of the house. She sent back our standard acknowledgement that she received the info, "K".

There was a white fence along the side of the house. I opened the gate and began walking back along the side of the house until I came to a set of stairs that lead up to the second floor deck. I took a deep breath, rolled my shoulders and started up the stairs. I could see a few, soft white lights around the deck, and I heard music coming from in the house.

Before I reached the deck level, a very large, very well built figure came into view. I couldn't really see what he looked like yet, but I could tell immediately that he was huge and he worked out way more than I did.