memory-box
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Memory Box

Memory Box

by Smoothandlovely
20 min read
4.72 (5100 views)
gay malecrossdressingoral sexanal sexromance
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Memory Box

The fading evening light came through the large window facing the open field with the old, dirt road leading to the woodlands as I sat at the dressing table in my sister's bedroom deep in thought. She had moved out several weeks ago, heading for San Francisco and a new job at a start-up AI firm and since our father passed away three years ago she had been the only one living in the family home. Dad left the house to both of us in his will and we had an agreement to share the upkeep and not sell it unless it was mutually agreeable to do so. The place had quite a few memories for me but since I had my own place in another city, I would not be living there so it was an easy decision to agree to sell it once Jackie moved away.

I had no plans for the next week so I took the opportunity to spend a few days looking around the house by myself, talking to the various resident ghosts, walking through what is left of the woods that I remembered from childhood, letting nostalgia run its course while exorcising some of the memories that still lurk in the dark recesses of the not-too-distant past. Jackie knew of my plans so before she left she made a point to leave a small box for me on her bed, neatly wrapped in pretty paper with soft colors, shiny ribbon and a matching bow. She always had a flair for the dramatic and a wonderful sense of style, and nothing allowed her the opportunity to showcase her passion than when she prepared gifts for the family and her close friends on special occasions. I smiled and laughed to myself when I first entered her room to find the package and an envelope near the bow with my name handwritten on it in flowing script. I knew that whatever was contained in the box would be nice since the days of giving presents that serve to embarrass each other were long gone. I opened the envelope and read the card slowly so I could savor the moment, one of the last of its kind in this hollow place.

"Dearest Brother,

I trust that your trip home was uneventful and that you will enjoy your visit. The empty house will be strange for you at first but I expect that your memories will keep you company and provide comfort for you as mine have done for me over the last couple of years. We shared many good times here together and I will always remember them and us as we were then.

This box is not what it may appear to be at first so please don't be disappointed when you open it. It is not from me per se, its contents coming mostly from your memory boxes that I found while going through the various cubbyholes in your room. I left it here as my personal gift to you and I know that you will understand it soon enough. Please consider it as a small token of love and affection for someone special to me and with whom I shared so much, for so long.

Love always,

Jackie

PS: After you leave and have some time to process your thoughts, please call me to tell me all about your stay."

The more that I thought about the unopened box after reading the card, I became apprehensive as well as curious. Jackie was a unique soul; open, loving but mischievous. She was two and a half years my senior, but we were close enough in age that when we reached our late teens we became close friends as much as siblings. As the years passed we found it easy to talk openly and frankly about anything and everything. I learned about her love life from high school through college, and her sexual experiences, disappointments and bad break-ups; I confided in her when I first came out and had to deal with the pain and heartache of losing some friends and facing scorn from others because of it. She never waivered in her love and support for me even when our parents struggled with my lifestyle choices, although I knew that there was a limit to how much she would take. At times of extreme stress in her life, she could come across as a bit of a cold bitch but these periods never lasted long with me.

I placed the card on the dressing table and looked into the mirror, inspecting the smooth skin but also noticing the sad eyes. I didn't expect the past to be such a heavy weight although I knew that some of the memories contained in this house would not be easy to relive. Jackie's note was warm, but it also was slightly melancholy.

Removing the bow and ribbon, and unwrapping the paper was something that I did carefully unlike the holidays from childhood which left only scraps of paper littering the floor. Opening the box then revealed several small bundles of soft-pink colored tissue paper, taped closed, each with its own small bow. I took them out, placed them on her bed according to size and wondered which to open first. I was curious and excited by what I might find hidden in these little parcels.

I chose the largest first and when I peeled away the paper I found a sheer, literally see-through, white satin robe which immediately triggered a memory that gave me pause. As I held it in my hands I was amazed at the softness of the fabric and how it rested upon my hands like a second skin. It was exotic in its look and erotic in its feel, truly lovely unlike the memory it summoned up.

I sat on the bed and looked over at the mirror on the dressing table, noticing a faint glow reflecting from the setting sun coming through the window. The room was now dimly illuminated and a surreal calm hung in the space like a fog without the benefit of a gentle breeze to disturb it.

I glanced down at the robe in my hand, fighting against the feeling of being transported to a place in the past that I did not wish to visit again but powerless to avoid. Standing up, I placed the robe on the bed and walked to the dressing table, stopping to look into the mirror and the soft glow that emanated from it. What was reflected in the mirror was not my sister's room but another bedroom with lighter, more modern furniture, and two men, one being me but at a younger age. The second man was someone I recognized as one of my college professors, sophomore year art history if I remembered correctly. In his outstretched hands he held a sheer white robe, the one on the bed. As he slowly moved toward me in the reflection, he offered the robe to me in a manner suggesting that I put it on. I sensed the same apprehension that I felt at the time and the confused look on my face indicated my surprise and uncertainty.

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Without much thought about what I was doing, I slowly removed my shirt, jeans and shorts, and after placing the clothing on a chair, I walked to the bed to pick up the robe and slipped it on. The sheer fabric felt cool and made my skin tingle with erotic energy that almost crackled in the dim glow of the bedroom. Glancing in the mirror I saw my reflection in a see-through robe standing with my back to my professor who rested his hands on my shoulders as he bent down to kiss the back of my neck. Looking closer I saw that I had an erection almost poking out of the robe and I could feel, or imagine that I felt, the robe being lifted and another stiff penis pressing against the crack of my butt.

I could feel hands sliding down my arms and moving around to my stomach before continuing down to gently gasp my stiff dick. A hand then firmly took hold of my balls while his rock-hard cock inched closer to the opening of my anus. Silently and slowly, I bent forward, spreading my legs in the process and placed my forearms on the dressing table which brought my face closer to the mirror, and allowed me to look intently at the scene on the other side. I saw the younger version of myself leaning onto the dressing table while staring into the mirror, watching the reflection of my college professor as he commenced sodomizing me. Despite the pain, his stiff dick continued going in and out of my ass, stretching my anus, probing my insides relentlessly as he moaned and spoke to me, telling me what he planned to do to me and how much he enjoyed fucking his sissy bitch. After about ten minutes of thrusting, he let out a cry and pushed his cock balls deep into my ass and shuddered, releasing torments of hot semen into my bowels. We remained locked together like two dogs sharing a knot as he held me tight and let his cum drain into me. Eventually, he was satisfied and pulled out without fanfare, allowing semen to flow from my anus down my legs. As he walked away into the darkness, I straightened up and felt the sticky liquid running down my legs to the floor.

I removed the robe as I walked to the bathroom to clean up. There were no streams of semen running down my legs now but there was a dampness, possibly the perspiration from anxiety, that lingered on the skin between my legs. As I washed up I remembered this after-school meeting with my professor at his apartment. He gave me a nice sheer white robe to wear while he sodomized me, spoke nicely while calling me his sissy bitch, and then, after the semester ended, I never heard from him again. I told Jackie about this first encounter with him and how I felt used, simply a fuck-toy for an older, more seasoned and controlling man. She was quick to point out that women endure this type of treatment almost daily but then went on to console and comfort me, telling me to be more selective before spreading my legs for someone, smacking my ass to make the point. I laughed out loud and realized how much I missed her guidance, rough edges and all.

Folding the soft transparent robe, I placed it back on the tissue paper. If this was to be a journey down memory lane orchestrated by my sister, then let it begin. Not bothering to dress, I sat on the bed naked and picked up the next parcel. Carefully I unwrapped the paper while wondering what I would find and took a deep breath when I saw the lemon yellow, women's high-cut, Brazilian bikini bottom with side ties. Oh my god, they looked as lovely today as they did the day I bought them for what was to be my first spring break in grad school. I remembered showing them to Jackie when I brought them home and if I remember correctly her first words were, "You fucking slut!"

My body has changed a bit over the years but not that much that I couldn't look as sexy today as I did then. I slipped them on and adjusted the ties, then proceeded to gaze into her full-length mirror while I turned and modeled my summer swimwear for an audience of one. I admitted to myself that I could still pull it off and became aroused as I watched the model in the large mirror.

When I looked at the dim glow in the small mirror on the dressing table, I was drawn to look closer at the scene that played out on the other side of the glass. It was a brightly lit hotel room with sliding doors open to reveal the ocean in the foreground after the pool, waves breaking on a white beach, and people partying around the pool bar. As I settled into the scene I could see several couples in the room, young women laughing, some naked and some topless, and naked young men gathered around a large chair where one of their group was sitting while someone else was on their knees performing fellatio on him as entertainment for the group. The person kneeling was wearing yellow bathing suit bottoms down around one of their ankles and it all flooded back.

It was the third day of spring break in Cancun, and there was a lively mixed crowd with very few inhibitions. After lunch by the pool followed by margaritas and tequila shots, a large group went to a fellow's hotel suite to get out of the sun for a while. A couple of the girls went to take a shower together and wound up naked and very involved with each other in the bed afterward, and some of the guys got aroused watching the display. Bathing suits came off and I wound up kissing a few guys before winding up on my knees with a handsome guy's cock down my throat. The first one led to a second and by the time I was on my third blowjob, my bottoms were peeled off and my ass was being fingered by I don't know who. My stomach soon held three loads of semen and there were a couple of other fellows who still waited for a turn with my mouth. Another guy was spreading lube on his erect penis, and I knew what that foretold.

A young blonde guy, number five I believe, took his place on the chair and I looked at his handsome face before I bent down to lovingly kiss his erect penis. I took it deep into my mouth, letting the head begin to gently inch down my throat and it was then that I felt strong hands on my hips and my anus being spread apart by a large stiff dick causing me to gasp and moan out loud. I groaned in pain and aside from the cheers from the assembled group I heard a voice simply say, "Shut up cunt!"

Oblivious to the pain of the probing and thrusting, I felt soft hands caressing my head as I worked on the lovely cock in my mouth. Soon they gripped my head from the back to hold me firmly as the young blonde shot loads of hot semen into my mouth with the quantity forcing it out the sides. I swallowed repeatedly and savored the sweet taste as it lingered long afterward.

The sodomy was rougher than I usually like but once I settled into it I found it enjoyable as well. When the young blonde got up from the chair a gorgeous slim girl took his place. She grabbed my head and pressed it into her vagina which smelled of sex, and had me use my tongue to lap up the semen that was dripping out as well as to stimulate her clit. When I finished I was worn out and had ingested enough semen to fill me until a late dinner.

I rose from my knees, scooped up my bikini bottoms and walked toward the bathroom to wash up. On the way I encountered the young blonde and he gave me a gentle kiss on the lips and thanked me for what I did. It was a sweet gesture, a one-of, that I greatly appreciated and he asked if I would join him and some of his friends for dinner. The offer made me laugh and I told him that it was nice of him to ask but I would have to see how I felt since I was quite full at the moment. He laughed at the joke and said he understood but that I should consider it an open invitation just in case.

I sat at the dressing table as the feelings of nostalgia swept over me causing a tear to run down my cheek. As I wiped it away I thought about the young blonde who appeared to like me and with whom I had one or two nice meals and a lot of fun but who, at first, neglected to share with me the fact that he was seeing someone back home. I told him that I would not come between two people who were in a relationship but he could call me if the situation changed; he never did.

When I returned from my holiday Jackie could tell that something was bothering me even though I had fun stories and great photos to share with her. Eventually I told her what happened and she did not offer advice or consolation, but said prophetically, "That sucks but it's life and best to move on."

With a sigh, I slipped out of the bikini bottoms and rewrapped them in the tissue paper. I thought to myself that one day I would unwrap them again and wear them on the beach for some lucky guy. Yes, one day.

There were two small parcels left but one was much smaller than the other and that was the one that I chose to save for last. I unwrapped the larger one and was greeted with a surprise and a note. The surprise was unexpected and somewhat unfamiliar but intriguing to say the least.

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The parcel contained a pair of cranberry-colored, tanga brief lace panties with a matching lace bra. I studied them but did not immediately recognize them as something of mine, particularly since I rarely wear bras, opting instead camisoles if I want something sexy. I moved on to the note and read it with curiosity and anticipation:

"I am confident that these items will not ring a bell with you because, unlike the other things in the box they are not anything of yours. These are from me! The night that I met Mickey when he opened his restaurant, I was wearing this lingerie set and I always believed that it brought me good luck in the romance department. Mickey loved them and asked me to wear them on special occasions so I did just that on numerous important dates and when I wanted to get my way with him.

"Now, don't get creepy on me since I have had many identical sets and while these have only been gently used, I washed before I wrapped them for you. I felt that they brought me good luck in my love life and hope they can do the same for you, if you choose to wear them. Plus, I am sure that you will think of me when you put them on.

Bonne courage."

The thought of wearing this set was irresistible so I gently slid the panties on and then slipped into the bra. Surprisingly the bra felt comfortable and I could feel my nipples tingle under the lace. Maybe I have been missing something all these years and I should rethink my intimate attire when I get back home. The panties were perfect and made me feel very sexy so I decided to wear the set a while longer. Thank you, Jackie.

Without fanfare I opened the last package and found a pretty gold anklet that was sent to me as a Christmas gift from the blonde fellow from Cancun. It had been more than six months since I had seen him and I had given up on the thought of ever hearing from him again. He sent this to me with a holiday card telling me that he had thought of me often and wondered if I remembered him and asked how I was doing. He included a business card with his cell phone number on the back, and said that if I were inclined to call he would enjoy speaking to me again. Yes, I would be inclined if he told me that he was no longer in a relationship, but those words were not part of his note. Regardless, my dear sister included his business card...just in case.

As I sat there, I looked into the mirror and watched as the scene from Cancun reappeared and morphed into a closeup view of the naked girls in the bed, whereupon one changed into a handsome young blonde man lying on his back and the other transformed into a pretty, young feminine man wearing a cranberry bra while straddling the other. They moved rhythmically, clearly engaged in sex and moaning with ecstasy. My body was tingling with anticipation and I wanted nothing more than to feel his lips on mine and the ache of him penetrating me.

I left the chair by the dressing table and went to lay down on Jackie's bed to clear my head of all the memories from the past few hours. Digging up all these things takes its toll, but it is a cathartic exercise nonetheless. Unconsciously I reached down and began to rub my penis through the panties while lost in thought and soon had a stiff erection. It would have been very easy to have an orgasm but I wanted something more and to stay sharp in order to focus.

I got up and went to retrieve my pants from the chair and remove my cell phone before returning to bed. I took a deep breath, picked up the business card and dialed the cell number on the back before procrastination allowed me to change my mind. The call was answered on the third ring, "Hello."

"Hi, Kyle. This is Philip, we met early last year in Cancun if you remember."

"Hey, Philip, it is great to hear your voice. Of course, I remember. You are a hard person to forget," he responded enthusiastically.

"It's sweet of you to say it but I'm sure it's an exaggeration," I blurted out.

"Really? You were wearing those fantastic yellow bikini bottoms and very 'outgoing' if I recall," he said with a laugh.

"Yes, you do remember. And you gave me wonderful kisses and shared a couple of very nice meals together," I replied.

We had a pleasant chat and talked about our lives since Cancun but never the elephant in the room. Not wanting to drag out unpleasantness, I put it on the table in a frank manner, "Kyle, when we left Cancun you told me that you were in a serious relationship and I said that I was not prepared to get into the middle of that, regardless of how I felt about you. When you sent me a nice gift this past Christmas with a card, you never said what was happening one way or the other. As much as I wanted to call you, my feeling about your relationship has not changed. I called today because I wanted to put some closure to what is happening between us so the best way that I know to do that is ask a simple question and hope for a simple straight answer. Are you still involved with someone or is that over?"

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