My Sissy Diary
- 3 years ago
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Author’s Note: Thanks for reading my Valentine’s submission! When finished, please take a few seconds and rate this story – one click is all it takes. And, if you have a minute, leave me feedback and tell me what you liked or didn’t like. Cheers!
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On occasion someone will ask me about my favorite Valentine’s Day memory. I usually reply it’s from the sixth grade when Jeff Hill asked me to ‘go with him.’ It lasted all of four hours and we only held hands, but he was my first love. That may seem to be a flippant answer but I’m reluctant to share my most favorite with the casual acquaintance.
But, for you, I’ll make an exception.
It was my freshman year in college and I had been dating this guy (I’ll call him Dave) for almost a month. From the moment we got together, I knew something was different about him. Maybe it was the way our personalities meshed or maybe it was the right combination of pheromones, whatever it was, we hit it off and I was walking on air. It’s as if I’d known him for years. The only problem was I didn’t know what to give him for Valentine’s Day.
You see, I was being a little guarded about my feelings for him. After all, it was my first year in college and my main focus was on school, not on some guy three years older than me. And after the debacles of my high school romances I’d made a vow to myself to not rush into a relationship. Of course, fate intervened at a house party in early January and it became crystal clear we were attracted to each other. He called two days later to ask me out.
We’d been on quite a few dates in a short amount of time but had never progressed past some serious kissing and a little light groping. I knew he wanted to take it farther but since I wasn’t giving any indication I wanted more, he never pressured me and would stop when I asked him – a perfect gentleman, through and through.
The truth is, a part of me did want more and after a couple of weeks I started daydreaming of what Dave’s body would feel like naked next to mine. It’d been quite a few months since I’d had sex and I craved that full feeling you have when someone’s inside you. However, the little voice in my head kept reminding me of my vow.
Valentine’s Day that year fell on a Sunday and we had a brunch date. A few days before I was out shopping trying to find an appropriate gift. All of the Valentine’s themed gifts marketed for couples hinted at a more serious and intimate relationship than we what we had at the time. I liked Dave a lot but I didn’t know if it was just infatuation or something more serious, and I certainly didn’t want to send the wrong message. I finally settled on a coffee mug depicting some cute critter holding a red heart-shaped balloon among a crowd of other nearly identical critters with a caption at the bottom that read ‘You’re one in a million!’
Lame, I know.
That evening I was in my dorm room plodding through Chemistry homework when my roommate, Sheila, my best friend since middle school, came in and closed the door softly. With an odd smile on her face, she leaned back against the door and stared off into space. I asked her what was up.
‘Oh, Michelle,’ she said dreamily, ‘when Dave gives you his Valentine’s gift you’ll want to marry him!’
It took my brain a moment to process what she said. Apparently, Dave had run into Sheila at dinner time, asked a few questions about me and told her what my gift was. As she knew me better than anyone else, she knew it was a perfect way into my heart. I pummeled Sheila with a barrage of questions but she wouldn’t give as much as a hint.
This only added to my arousal.
On Saturday night, Dave and I went to a movie he picked out. I don’t recall now what the movie was, just that it was one of those pleasant romantic comedies and we both enjoyed it. I do recall it was bitter cold that night as February nights in Michigan are prone to be and we got to his car to find the windows frosted over, inside and out. We sat in his little hatchback in the parking lot waiting the defroster to kick in and do its job. To kill time we started making out.
I should mention at this point Dave is a really good kisser, knowing when to go soft and gentle and when to go deep. When he’s on his game, his kisses are soulful and full of meaning, and he was definitely on his game that night. Our bulky winter coats prohibited any real groping but I’m sure if we weren’t wearing them we’d have been all over each other and I wouldn’t have been responsible for my actions. Those warm butterflies which usually inhabit my stomach when I’m with someone I like had set up shop noticeably lower.
‘So…, do you want come over or should I take you back to your dorm?’ he asked after the car warmed up.
I was warmed up, too, and didn’t want to the evening to end just yet. ‘Let’s go to your place for a while.’
I admit I cooled off a little on the ride over, but once we got there I reheated quickly. We started out on a loveseat but ended up on the floor with me on top. It’s a blur in my mind how we got there but I’m certain it was my doing. There we were in the semi-darkness, breathing hard between bouts of kissing, my thigh pressing against his hardness and I’m estimating his size. We became very still and very aware of our situation as we stared into each other’s eyes and I debated what to do next.
God! How I wanted him!
I wasn’t quite ready to have sex with him but I wanted to do more than just kiss. I made up my mind. I tugged at his shirt, freeing it from his jeans and pushing it up. The skin of his body burned fiercely under my hand as I caressed him. I trailed kisses down his neck to his chest, swirling my tongue around his nipples. The feel of his rock-hard cock between us reminded me of my intentions, and I kissed down his stomach to the top of his jeans.
Dave had become incredibly still and hardly seemed to be breathing as my fingers fumbled with the button-fly of his jeans. Exposing just the tip, I kissed the wet, slippery head and he moaned his approval. Emboldened, I pushed his jeans and briefs down to his knees and wrapped my hand around his shaft. The heat of his chest paled in comparison to the heat of his cock. The skin was taut and smooth and I marveled at the electric tension humming just below the surface. When I held it lightly I could feel each beat of his heart as his cock pulsed. I leaned in and wrapped my lips around his fleshy head and heard a sharp intake of breath.
It felt good to have a cock in my mouth again after so many months, but it felt even better that it was Dave’s. I’ve always loved the feeling of control I have over a guy when I’m sucking him off. I licked and sucked Dave until he gave a strained groan and pulled me up. He kissed me deeply, his exposed cock pinned between us and I knew he stopped me before he came in my mouth. His consideration made me want him even more and I ground my crotch against his rigid shaft, my tongue plunging wildly into his mouth.
His hands roamed from my ass up to my head and around to my breasts crushed between us. My butterflies were long gone and had been replaced by something warm, wet, and urgent between my legs. It wouldn’t be long before I would be past the point of no return and unable resist from fucking his brains out. I sat up suddenly, my hands on his chest, my hips moving automatically, my pussy lightly rubbing on his shaft, and knew what I had to do to defuse the situation.
I slid lower and took him between my lips again, this time to finish him off. My hand and mouth worked feverishly in tandem and, incredibly, his cock grew harder to the point of bursting. With a gentle squeeze of his balls, jets of cum pulsed into my mouth. I swallowed and another two spasms shook his cock, and I tasted more of his seed. I swallowed again and laid my head on his stomach, reveling in what just happened.
I’d given numerous blow jobs before but this was the first time I had ever swallowed. Before, I
‘d discretely spit into a tissue but something about Dave made me want to swallow. He didn’t taste that different from the others so that wasn’t it. It’s hard to explain but somehow swallowing made me feel closer to him. I lay on his stomach soaking up his warmth when another first occurred:
He lifted my face to his and kissed me, his tongue probing my mouth gently.
Not one of the other guys ever came close to kissing me after I sucked them off. I wrapped my arms around Dave and kissed him deeply. He rolled me onto my back and explored my body with his hands, every hill, every valley, driving me to the edge of reason. If I wasn’t careful I was going to be spending the night, and I didn’t want that, not yet. I gently pushed him away and looked at the clock.
It was after one in the morning and he was going to be picking me up at ten for our brunch date, so I made the excuse I needed to get some sleep. Truth be told, I spent the next several hours awake in my bed, my body buzzing with adrenalin, my mind replaying what happened over and over, my pussy aching to be touched. I considered masturbating but choose instead to bask in the exquisite agony that is delayed gratification.
In the morning the lips of my vagina were full and puffy, my folds wet and slick, and I knew I would come with little manual stimulation. I was extra careful in the shower to not get myself off. In some way I thought it would be unfair to Dave if I did.
Dave picked me up on time, prompt as always, and we enjoyed brunch and each other’s company, talking just like before. We were both completely at ease, as if the previous night hadn’t happened, except it had, of course. On the way back to his place, my butterflies returned, flitting low and deep within my engorged sex.
Something wonderful was in air as we walked in, the smell of fresh baked cookies. For my gift, Dave presented a metal container filled with delicious homemade chocolate-chip cookies and fudge. Stunned, I asked when he baked and he confessed he made them after he’d dropped me off. I figured he was up until after three in the morning baking for me. It was such a simple thing, really, but it was from his heart and at that moment I knew exactly what Sheila was talking about – a part of me did want to marry him.
A different part of me wanted something immediate, something much more physical. Moist heat spread from the center of my body. I wanted – no – I needed some part of him inside some part of my body and I wasn’t going to be too fussy about which parts. He just stood there, smiling at me until I grabbed his hand and pulled him to the bedroom. The instant the door was closed I was on him like some ravenous animal.
My lust was spilling out of me, literally, as my panties were soaked. His hands ran over my skirt, caressing my ass and I pulled him closer to me, encouraging him. We sank to the floor, his fingers working the buttons on my blouse and the clasp of my bra until my heaving breasts were free. First his fingers, then his mouth teased at my nipples until they ached. I held his head tightly against my chest while his tongue lavished me and he undid my skirt.
He kissed his way down to my stomach and with one sure move pulled my skirt off. He looked me in the eye, checking to be sure this was what I wanted. I gave a slight nod and the next moment he was carefully rolling my pantyhose off and the only thing between him and my swollen pussy were my cotton panties. A second later those were gone and I lay before him, totally exposed, totally vulnerable. If he wanted to fuck me I wouldn’t have stopped him, I would have welcomed him.
I waited.
Instead, he leaned down and kissed me softly on the stomach, followed by second kiss lower and a third lower yet. It was my turn to be breathless as I realized I was about to be eaten out for the first time in my life. A brief moment of anxiety struck me as I worried how I tasted. That anxiety dissipated quickly as his kisses moved lower still, my legs parting automatically for him as if his face belonged there naturally. The instant his lips grazed my clit a shudder ran through my body and I experienced my first orgasm that wasn’t self-administered.
His mouth continued lower and I felt his tongue part my lips and plunge deeply into my pussy. I moaned softly as his tongue, so magical in my mouth, played so magically over my sex, exploring every crevice, every nook and every cranny. When his mouth returned to my clit it only took a few flicks of his tongue before I came again, my thighs squeezing his head.
Dave came up for air and we kissed, yet another first as I tasted my own juices on his lips. His fingers played lightly over my body, exciting my nipples. The urgent need to be fucked was gone, replaced by a feeling of inner warmth and peace. I could feel his hardness against my side but I wanted to wait and told him so.
‘That’s all right,’ he murmured, his fingers playing across my pussy. ‘There’ll be plenty of time for making love later. For now I just want to taste you again.’
Making love. Coming from any of the other guys I’d been with, that phrase would have been comedic relief. But from Dave, those were exactly the right words to say. I knew when we did have sex, it wouldn’t just be fucking, it would mean so much more.
I rolled Dave onto his back and disrobed him, kneeling between his legs, lovingly sucking his beautiful cock. With firm but gentle hands he turned my body around until my pussy settled on his mouth. His fingers dug into the soft flesh of my ass as we ate each other out.
Even now I can close my eyes and recall everything about that experience: the scent of his skin, the hard smoothness of his shaft, his hot breath on my inner thighs, the salty slickness of his pre-cum, the slippery velvet of his tongue in my pussy, the tightening of the skin around his balls as he approached orgasm, the touch of his lips on my clit, the twitching of his cock in my mouth when he came, the shaking of my body as a third orgasm, my strongest yet, thudded through me.
Every nerve hummed happily as I rolled onto the floor. A chord had been struck deep within me, resonating through my entire body and I knew I’d never be the same. I’d never been so alive! I could sense the earth turning beneath my back, hear the ticking of a clock in the next room, feel the heat radiating from the body next to mine. I laughed in sheer joy once I caught my breath. No one had ever made me feel so much and no one has since, except for Dave. He still does on a regular basis and my body resonates to this day.
Sheila’s prediction came true – I did marry him. This coming February will be the twentieth Valentine’s Day we’ve spent together and I’m amazed at how fast the years have passed by. Twenty years of fun, of romance, of laughter, of life. To celebrate I’m planning something special this February 14 so we’ll have more memories to last another twenty. Maybe someday I’ll share it with you.
So, the next time you ask a woman about her favorite Valentine’s Day and she tells you the brief tale of Jeff Hill and the sixth grade, look for the twinkle in her eye and give her a knowing smile. You’ve heard the whole story now.
And that lame mug I gave Dave? He uses it to this day.
Josephina
- 15.08.2022
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