tagLesbian SexSydney's Adventures Ch. 3

Sydney's Adventures Ch. 3


I'd been living in the sorority for a couple of months now and it was a great time. I had one of the upstairs rooms, which I shared with three other girls who were all really nice. The only problem with the room, or so I thought initially, was that there were only two queen-sized beds; I shared one with my best friend, Cindy, and the two other girls, Jenny and Ariana, shared the other bed. Cindy and I had been roommates in the freshman dorm and had applied to join tri-delta together (which is where we met the other two girls).

I had never had sex with another woman before, but the morning after the sorority's pledge party I had woken up, covered in cum, in a bed with Cindy. We fooled around a bit that morning and I discovered that I was decidedly bi-sexual and didn't mind sharing a bed with Cindy at all. Judging from the occasional moans and groans I heard, I don't think that Jenny and Ariana minded the living arrangements either! Still, they were more into boys than Cindy and I were and when the day before Valentine's Day rolled around they both had dates while, much to our dismay, Cindy and I did not. We decided to make the best of it though, and go out with each other. We drew straws and I got the long one, meaning that I had to be the "boy" for purposes of the date—I had to make the reservations for dinner and get ready somewhere besides our room (we couldn't get ready together because then there would be no surprises on the date!).

On the morning of Valentine's Day I woke up and hopped into the two-person shower, which Jenny was already in. While helping wash each other's backs we talked about our plans for the day; Jenny said that she and Ariana figured that their dates would last all night, and that we shouldn't expect them back until the morning. On my way out to class I relayed this information to Cindy—it was nice to know that we had the room to ourselves all night!

My classes seemed to drag on forever. In psychology we did some sort of personality test with the arrogant Dr. Arton; I didn't really concentrate much on it because I was thinking about my date tonight with Cindy. I had made reservations for us at a little Italian restaurant that was supposed to be very intimate. In my backpack I had already stashed some makeup and jewelry, my favorite red velvet dress (by Bebe) and a pair of strappy, black high-heeled shoes (9 West). I was going to change in the girls' room across the hall from my own; the four girls in there were freshman like us and didn't mind if I joined them while we got ready for our dates. I met Cindy at Ms. Somers' music class and we sat in back together and enjoyed the Brandenburg Concertos. We couldn't keep our eyes (or hands!) off each other and I think we gave some guy sitting in the back row with us quite a show. We were both giddy with excitement as we walked back to the sorority house.

Since I wasn't allowed in our room all afternoon I stayed downstairs and watched TV in the common room. A couple of girls were watching an episode of the Young and the Restless and Victor was doing something horrible to Jack. Of course that seems to be true of just about every episode.

About two hours before I was supposed to pick Cindy up for our date I headed upstairs to get ready. The first thing I did was wax my whole pussy—peach fuzz was beginning to grow in from the last time and I wanted to be as smooth as possible for Cindy. Then I took a shower washing and conditioning my hair. When I got out I stepped into a flurry of activity with five naked (or nearly so) bodies flying around the bathroom getting ready. Some girls were getting into the shower while others were putting on makeup or trying on clothes, seeing what looked best and asking for opinions. Somebody had put on Britney Spears 'Oops!…I Did it Again' and we were all singing along over the roar of hair dryers and the shower. After rubbing body oil over myself to keep in the shower's moisture, I managed to fight my way to the mirror. I stopped for a moment to admire what I saw there. My dirty blond hair was still wet and plastered to my body and you could hardly make out the golden highlights. My blue-green eyes were sparkling with anticipation over the night to come and my full lips couldn't help but twist up at on the ends in a smile. My 38d breasts jutted out from my chest with the impressive perkiness of youth. They had only really developed over the past two or three years and I still marveled at their fullness. Cupping them in my hands I held them together, enjoying their softness and substantial heft. I tweaked my nipples and watched them harden. I make it a point to tan topless (and naked if possible) so that I have a nearly perfect tan except for a tiny 'V' in front and an even smaller one in back from my thong bikini bottom. My flat tummy has just the vaguest hint of a six-pack and I keep my long legs and round ass in excellent shape by playing field hockey on the university team.

Snapping out of my reverie I let my breasts go and began blow-drying my hair. Once it was nearly dry I stopped and changed into my dress. Since it was very low-cut in back and had spaghetti straps there was no way I could wear a bra—even a strapless one would have shown. And anyway, I love the feeling of my unconstrained breasts bouncing and jiggling with every step I take! Even without a bra though, you could definitely see my cleavage because my boobs were pressed together by the tight-fitting, stretchy bodice of the dress. I mentioned that the dress was low-cut in back and when I say low cut, I mean low cut. You couldn't quite see the cleavage of my butt cheeks but it was close! The only modest thing about the dress was that it was floor length. Still, the bottom was tight fitting and there was a slit on the left side that reached my upper thigh; every time I took a step I exposed a generous amount of leg and nearly uncovered the matching red velvet thong I slipped on underneath the dress. Going back to the mirror I decided on some fire engine red lipstick, which matched the color of my dress. I went all out for Cindy putting on foundation, blush, eyeliner and mascara. I wore two ruby stud earrings. Finally getting back to my hair I went for an elaborate up do. It took me a couple of tries, but with perseverance and enough hair spray I finally got it just right. I left a few tendrils on either side of my face to frame it. The final piece of the ensemble was a black velvet choker to match my black 3" heels. I looked at the clock and discovered that I was about five minutes late in picking up Cindy. Hurrying across the hall I couldn't believe that I had butterflies in my stomach as I knocked on her, I mean our, door.

"I'll be right there!" I heard Cindy yell from the other side. After a few minutes of nervous anticipation the door opened a crack and Cindy slipped out without letting me see what was inside. Not that I would have noticed anyway, because I couldn't take my eyes off of Cindy. She looked stunning in a "little black dress", pantyhose and high-heeled shoes. She had a beautiful ruby and gold necklace that matched the red and blond highlights in her hair and, like me, she had simple ruby stud earrings in her delicate ear lobes.

"Wow, you look fantastic!" we both stammered at the same time. I reached for her and we embraced in the hallway, our breasts crushing against each other, our tongues seeking and finding one another in a long, wet kiss. We must have held each other in the hallway for at least five minutes as our tongues and hands explored each other's mouths and bodies and I could feel her hard nipples pushing into my breasts.

"Mmmmm…we really should…mmm…get going if we…mmmmm…want to make it…to…mmm…dinner…" I managed to get out.

"Can't we…mmmm…just…stay…mmm…here?" She asked, sliding her hand through the slit in my dress.

"No…we have to…ohhhh…at least make the…ahhh…the pretense…of going out." Cindy had found my velvet covered pussy and was sliding her fingers back and forth across it. With a burst of willpower I pushed Cindy away from me. "Come on, the limo should be waiting for us downstairs."

"A limo huh? You must really want to score on this date!" Cindy said grinning from ear to ear.

"Yeah, I don't know where I'm going to find the money for it, but you are definitely worth it! Now come on!" Taking her arm in mine I escorted her downstairs where the limo was indeed waiting for us.

The chauffeur helped us in and we snuggled together in the back seat.

"Where do you lovely ladies wish to go?" he asked, lowering the privacy partition.

"La Dolce Vida" I told him.

The driver raised the privacy screen and we pulled out.

"Now where were we before you drug me out here?" Cindy asked putting her hand on my bare leg.

"Wait a second!" I protested jokingly. "I'm not the kind of girl who goes all the way on a first date you know!"

"Well I am, and I'm the 'girl' for this date—you did get the…long…straw after all!"

"In that case," I slid my hand between her thighs "I should really…" I stopped in amazement. "Stockings?! You're too much! I thought you were just wearing pantyhose!"

"Pantyhose? On a date like this? No my dear, only silk stockings are good enough for you." She positively smoldered with passion and satisfaction as she sat back in her seat with her legs slightly parted.

With that I leaned over her and began kissing her hard while my hand continued snaking up her dress. When I reached her silk panties she sighed into my mouth.

"Open your eyes," I told her.


"Because I want you to see me devouring you."

Slowly she opened her eyes as we resumed kissing, and it was like our souls connected in that moment. There was no past, no future, only the two of us in the present. I lost myself in the depths of her emerald green eyes and time seemed to stand still.

The heat and moisture I could feel radiating through the thin silk covering her pussy brought me back and I eased the fabric aside with my thumb. Her eyes, still open and looking into mine, went wide with surprise and delight and then became half-lidded with lust when I began sliding my fingers up and down her juicy slit. Finding her engorged clit I gently massaged it while Cindy arched her back in ecstasy.

Just then the driver opened her door. "We're here ladi…" he stopped mid-word as he noticed that Cindy's dress was pushed up around her waist and my hand was buried in her bald pussy. "Uhm…excuse me…I'm sorry…I…er…I thought you noticed…uhm…we had…ah…stopped." The chauffeur was turning bright red with embarrassment.

"Oh, it's ok." I said, giving Cindy's pussy one last caress then licking my fingers off in front of the chauffeur. "I think that we are ready to get out!" I offered my hand to him and he helped me out of the car while Cindy hurriedly pulled down her dress. "Thank you," I said as the chauffeur turned to help the flushed, but at least covered, Cindy.

"You are EVIL!" Cindy whispered to me. "I'll get you for this!" Turning to the chauffeur she thanked him and we headed inside.

The restaurant turned out to be perfect for what we wanted. The walls were made of brick and there was a fireplace on one side of the dining area with a roaring fire. The tables were covered with long, cream-colored linens and each had candles and two red roses in a crystal vase. We were shown to a tiny table for two in a secluded niche next to the fireplace. A low wall separated us from the main dining area and provided us with a little extra privacy.

"Oh this is perfect!" Cindy exclaimed as we sat down. "I love it!"

"It really is nice isn't it? I'm glad you like it. And I'm glad that we're celebrating Valentine's Day together."

"Me too." Cindy leaned across the table and gave me a peck on the lips. "You've done a great job on our date so far."

"Except when we got here!" I said with a mischievous twinkle in my eye.

"Yeah, except for that. And trust me, you will pay for that!"

"Well I certainly hope that someone will pay. Dinner isn't free you know!" Somehow our waiter had materialized next to our table without us noticing. "This champagne," he continued with a slight Italian accent, "is on the house though." He poured two glasses. "Part of the Valentine's Day special."

"Oh, thank you very much," I said taking my glass.

"My pleasure. Here are the menus and a wine list. I'll be back to take your order in a few minutes. Until then, enjoy the champagne."

"I'm sure we will. Thanks." With that he nodded his head politely and disappeared back into the dining room.

"I propose a toast," Cindy said holding up her glass. "To the best Valentine's Day I've ever had, and to the most wonderful girl I've ever met."

"I'll drink to that." We clinked our glasses and took a sip of the excellent champagne—dry but with just a hint of strawberry fruitiness. "So, what have some of your other Valentine's Days been like?" I asked her.

"Oh you know, the usual. Horny high school boys in cheap tuxes trying to feel me up. I even got dumped by one boyfriend on Valentine's Day. And then the jerk wanted to get back together the next week! I guess his date wasn't all that hot."

We giggled and chatted about our past experiences and, before we knew it, the waiter was back at our table. "Are you young ladies ready to order?"

Before I could say anything Cindy answered, "Yes, I think we are. Sydney, since you're the boy on this date, would you order for me?"

"Sure thing," I stammered, picking up a menu for the first time. "I'll have…" I felt somebody's bare foot moving up my leg and quickly looked over at Cindy. She had the proverbial 'cat that just ate the canary' grin on her face and she let me catch a glimpse of the stocking she was holding in her hand. "Ahem…excuse me…Cindy will have the…" I could feel her foot burrowing between my thighs, "…pasta primavera, and I'll have…" Cindy hooked her big toe underneath my panties and pushed them aside, "…the spaghetti carbonnara." I closed the menu, relieved that I was finished ordering because Cindy was caressing my increasingly moist pussy with her toes.

"Wait, don't we want some salad?" Cindy asked with a wicked smile on her face.

"Oh, right," I grudgingly agreed and opened the menu again. "Could we get the insalata mista to split?" I said picking the first salad I saw.

"Of course Signorina. And would you like some wine?" the waiter asked.

"Oh definitely!" Cindy replied to the waiter. Turning to me with that wicked grin she continued, "I told you I was going to get revenge Sydney!"

"I'm afraid I'm not too familiar with wines. What would you recommend?" I asked the waiter, trying to block out Cindy and her wriggling toes.

"Well, since you are both having cream-based pastas I would suggest a white wine, perhaps a chardonnay."

Cindy's toes were continuing their wonderful dance across my pussy and I could barely concentrate on what the waiter was saying. I could feel her big toe gently probing the entry to my pussy. Just as the waiter was pointing to a 'Gr something Hills' wine Cindy slipped her toe into my pussy. I could feel my pussy lips stretch to admit her and, when the thick part of the toe was past, I swore I heard a little 'pop' as my lips contracted, pulling her toe deeper into my pussy. I tried to stifle my groan, but some sort of grunt managed to slip out.

"Ah, you know this one then? It is a very good wine."

"Sure." Cindy's big toe was wriggling around in my drenched pussy while the rest of her toes were squirming all along my slit like a caterpillar walking.

"An excellent choice Signorina. If you have any other…needs…" I could swear he paused knowingly "…please let me know and I would be delighted to help you in any way that I can."

"I told you I was going to get you back!" Cindy whispered as the waiter walked away. "And what do you think of the waiter? He seems pretty cute, don't you think?"

"Uh-huh" was all I could manage as her toes continued dancing in my pussy. She was now concentrating on the big one, pushing it in, then pulling it out. I could hear a vague squishy sound and I could feel my juices dribbling past my swollen lips and down my butt.

"Sydney, do you know what one of my favorite nursery rhymes was?"

"Uh-uh," was all I could stammer out as I felt a familiar tingling starting deep within me.

"Go ahead, guess!"

"Roses are red?"

"And violets are blue. But no, that's not it. Try again!"

"Ring aaAAAA…" Cindy's toe plunged into my pussy and I could feel the tinglies expanding, "…round the rosey?"

"Nope. It's 'This Little Piggy'. You know how it goes don't you? This little piggy went to market." She plunged her big toe into my spasming pussy and wiggled it around. "This little piggy stayed home." She wiggled the next toe up along my dripping slit. "This little piggy had roast beef." Another one wiggled. "This little piggy had none." Yet another went and I could feel my orgasm building. "And this little piggy," she began inching her little toe up my pussy until she found my clit, "ran wee wee wee all the way home!" With that she began flicking her toe back and forth across my engorged clit, sending me crashing into an orgasm. I gripped the table as hard as I could to keep from screaming as my pussy spasmed around Cindy's toes. My cum spurted over her foot, covering it in my juices and began trickling down my thighs. I could feel it pooling around my ass, creating an enormous wet spot on my dress and the plush, red velvet chair beneath it. I couldn't think as her toes continued their magical dance in and along my pussy and I felt a second orgasm rip through me.

"Please stop. I…I don't think I can take anymore…" I gasped out.

"But Signorina, I thought that this was the wine you wanted?" I couldn't believe that our waiter had returned already!

"How long have you been standing there?" I asked, blushing furiously.

"Only a few minutes." Looking at the growing bulge in his pants, I could tell he'd been there long enough. I must have turned the same shade as my dress. Trying to cover for my embarrassment he gestured to the bottle of wine and politely asked, "This was the wine you wished for I believe?"

"Yes it is." I had no idea.

"Excellent." He began opening the wine and I took the opportunity to check him out. Dark hair and eyes. Olive colored skin. Charming smile. Cindy was right—he was cute in that 'dark stranger' kinda way, although he wasn't particularly tall. He handed me the cork, which I had no idea what to do with, and poured a small amount of wine into my glass. I took a sip of the wine, which tasted vaguely of pears or apples and oak with a rich, buttery finish.

"Yes, this will do quite nicely."

"Very good," he said, and poured us two glasses. "I will be back in a moment with your salad."

"Look, he even has a cute ass!" Cindy whispered, perhaps a bit too loudly as the waiter departed.

"Shh!" I said, feeling my blush renewing.

"I think that you have embarrassed us enough already," Cindy said, wiggling her toes, which were still caressing my pussy "I doubt that I could add much!"

The rest of dinner proceeded without event, although Cindy and I both flirted shamelessly with the waiter. He must have had a good time with us too because he told us dessert was on the house! If we hadn't been anticipating the rest of our night back at the house so much we probably would have jumped the poor guy. As it was we both 'accidentally' brushed up against the still-large bulge in his pants on the way out. "We'll be back soon," I whispered into his ear as we left the restaurant.

The limo was waiting for us in front of the restaurant and we piled in, eager to get back to our room. We made out in the back again, slipping each other's thongs off, but we didn't have much time before we arrived back at the sorority house. We jumped out, paid the driver (including a generous tip!), and hurried upstairs to our room. Cindy stopped me outside our door and pulled a black velvet blindfold out of her clutch purse. Without a word she slipped it over my eyes and then opened the door. She brought me into the room and had me sit on a chair just inside the door.

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