“Allie honey, I’m on my way out. Hopefully the conference won’t last too long so I won’t back late tomorrow. My roommate Jessica called as she walked out the door, lugging a large piece of leopard print rolling luggage. She and I had been rooming together since I’d started at the university last fall. She was a junior and I really appreciated all of her great advice, she seemed so knowledgeable about everything.
“Okay, have a good time!” I shouted back to her, and then lingered just inside my bedroom door as I waited to hear it close. Once the deadbolt turned, I tiptoed out of my room then down the hall to her bedroom. But still I didn’t step a foot inside until I heard the car start and pull out of the driveway. A smile crept to my lips when I realized that I was finally alone. I had waited for this moment for awhile now and finally I reached forward and palmed the door to her bedroom open.
I walked slowly inside, taking the moment in. I loved her room, as well as the en suite bath. It had always seemed like a scene from an old movie; like Breakfast at Tiffany’s. I walked around the bed, running my palm along the plush fabric of her duvet then up over the ornately carved posts of the four poster bed. I felt a familiar tingle as wetness pooled in my panties as it brought to mind the sounds I stumbled upon just a few weeks before.
(It was late and I had gone to the kitchen for a glass of milk, but as I came back to return to my room I was enticed by breathy muffled moans coming from Jessica’s room. I slipped up to just short of the door and discovered it cracked just a bit. I couldn’t see much but I heard plenty. It confused me because I knew that her boyfriend had come and gone much earlier that night. My roommate was laid on the bed naked from what I could see and I dropped my eyes immediately, only to catch myself peaking again. Her hair was wet, her eyes were tightly closed, and she moaned quietly alternating with chewing furiously on her lower lip. I realized she must know that I’m down the hall and she didn’t want me to hear her.
“A little too late for that, isn’t it Jess?” I thought to myself, grinning as I blushed deep and hot. I allowed my eyes to travel downward where I could make out her hand kneading her full breast in her fist, tweaking a large distended nipple. Without a thought my hand traveled to my own breast and I allowed my fingers to graze my own nipple through the fabric of my camisole, gasping at the intensity of a simple touch. I slipped my fingers below the seam to caress the naked flesh of my own breast. I was so turned on!
My eyes returned to where she lay on the bed and only then did I see the large purple toy she held in her hand. It buzzed in a low rhythm, causing my knees to quiver. She gripped the end and rubbed the tip along the lips of her pussy and up to hover over her clit. Her moans grew louder for a moment but then she paused, reining herself back in. Then I was entranced to watch as she moved it down and pushed the tip and then its full length inside of her pussy. Pumping it in and out of her forcefully, she brought herself to a glorious orgasm. At the intensity of it all my knees almost gave out and it wasn’t until I saw her start to come to her senses that I turned and scurried back to my room, closing my door silently behind me.
That night I’d allowed myself to stroke my own clit gently grazing the outside of my own tiny opening with my fingertips. But when I felt how tight the opening itself was I was too afraid to push anything inside of it. There was no way anything would fit inside of me, especially not that monster that Jessica had, (it would tear me apart) but I couldn’t help but wonder. I went to sleep dreaming of what it would feel like to use that toy on my own virgin pussy. Sleep eluded me most of that night and I awoke the next morning exhausted, knowing I had to find a way to get my hands on that toy.)
Well my moment finally arrived a fitful three weeks later when Jessica was invited to attend a conference for work. The travel itself meant she had to leave out early in the evening today and she wouldn’t be returning until hopefully late the following night as well.
I then found my way to her nightstand, to the second drawer where I learned she kept it. Reaching in I quickly found it, and then withdrew the large toy. My tiny hand barely wrapped all of the way around its base and I stared wide eyed, second guessing my plan. Laying it down on the bed I watched it warily as I removed my clothing, folding them neatly into a pile at the foot of the bed.
For a moment I stood naked staring at my reflection in the mirror of her dresser. I scrutinized every detail and freckle, hating my body. While I did gain slight hips and breasts after puberty in all other aspects, I was behind. My breasts where definitely present but not full like Jessica’s, my frame was much slighter, and it didn’t seem to grown as much hair down there as she did either. I frowned, knowing there must be something wrong with me. I brought my hands down over my breasts where my tiny nipples stood at attention. Goosebumps emerged over every inch of my exposed flesh as they traveled lower over my hips then down over my pussy. The tiny smattering of hair there was darker than the blonde shade on my head but much softer in texture. My legs began to shake and I pulled the duvet back, climbing up onto the sheet, laying back into the fluffy pillows.
I lifted the toy to eye level and twisted the base feeling it hum to life. The vibrations were violent so I quickly dialed it back to about halfway then closed my eyes and lowered it slowly against my sex. The moment it touched my flesh a tiny moan escaped my lips. Oh, it felt heavenly! My stomach clenched deliciously and I slid it down further, grazing my tiny clit. My tight little pussy became molten, quivering and immediately craving more. I allowed the moans to echo freely off the empty walls as I pushed it harder massaging it heavily against my clit. I felt a growing urge in my belly but it scared me so I pulled it away.
“No, don’t stop.” A gruff voice came from the doorway.
My eyes shot open and I immediately opening my mouth to scream until I realized that I knew the voice. “Christian? Is that you?” In stepped the tall slim form of my life long best friend, Christian. He and I became friends as a result of the long standing work relationship that our fathers had. Their many projects over the years eventually led to long playtimes for Christian and I, and eventually he was ultimately motivated me to pick the college that I did. He and I said in my parent’s living room while he promised to keep an eye on me and help me to stay on track with my studies. Although he was two years my senior, we were incredibly close and it wasn’t odd for him to randomly show up, letting himself in. In all of the situations he had caught me in this was by far the most intimate. I reached down and grasped the sheet, pulling it up to cover my nakedness which also caused me to drop the still vibrating toy on the bed.
“Wh-what are you doing here? I stammered. He strode in without an answer; his eyes trained on the toy, and he picked it up. I couldn’t read the heat behind his eyes and I blushed deep red. “Um Christian, I was just…” He put his fingers to my lips, “I know what you were doing, Allie. I can show you how to make it feel better; will you let me show you?”
The look in his eyes was still heated but he wasn’t angry. I trusted him, and I knew he wouldn’t do anything to hurt me. So, silently, I nodded and he smiled.
“Good girl.” He quickly pulled the sheet back down and away from me, “Now lay back please.”
Watching him intensely, I did what he asked and laid back onto the pillows once more.
“Perfect, now open your legs for me… a little wider, just like that, hun.” He lifted the toy and began to trail it along my thigh, then over my stomach. I moaned softly then my eyes shot to his face and I blushed. He smiled, “Don’t be embarrassed sweetheart, this is meant to feel good. Don’t be afraid to moan as much as you like, I love to hear it.”
I started to smart back but pulled back and, chewing my lip, closed my eyes again. He brought the toy along the same trail he had marked before then continued a downward path to my sex. As it met against my clit once more I jumped but held my legs open and moaned deeply.
“Good girl.” He whispered.
Pushing the vibrating head against me firmly he soon had me writhing beneath him, starting to pull away.
“No Allie, don’t pull away. Just feel it, trust me, it’ll be worth it.” He grinned with a hidden secret behind his eyes, and he began to press harder. My moans became louder and louder as the urge began to grow larger once more.
Breathlessly I squirmed and panted at him, “Christian, I…oh, God…Christian!”
In a moment every nerve in my body exploded and my entire being shattered. The intensity of the moment caused spots behind my eyes and my back arched as I moaned loudly. Afterward, I lay silent for a few minutes, and then finally opened my eyes to see him standing above me smiling broadly.
“How was that?”
I sat up on my elbows, “That was amazing…but…”
His eyes immediately darkened. Oh my, he thinks he’s disappointed me.
“No! It really was awesome; I mean I’m still shaking. But I was really wanting to feel it inside of me; even more now in fact.” In that the cloudiness behind his eyes melted and he looked at me curiously.
“Wait Allie, you’re still a virgin right?”
I couldn’t answer through my blush so I only nodded.
“Wouldn’t you rather, I don’t know, do that with a person instead of a …?” He gestured toward the toy which now lay silent next to me on the bed.
I shrugged trying to appear nonchalant. “Well, um, I had never really thought about that.”
He nodded, “Well, you know you really should find someone that you trust for your first time, and then you can always use…that…later on.”
Well, he did have a point. But how would I find someone who would do that with me? A motion caused me to look over and I noticed him lightly stroking himself through the jersey material of his shorts.
“Wait, you want to…?”
“Yes Allie, I want to fuck you. I want to be the one to fill you up for the first time. I’ve wanted this for awhile, and you do trust me don’t you?”
I stared at him blankly but nodded. He slipped the waist of his shorts down, revealing his erection to me. I nodded in response but watched it warily as it hardened even more.
“Don’t worry, it will fit. It will be tight at first and it may hurt just a little but it hurts for everyone the first time. I’ll do everything I can to make this easier for you, if you’ll let me. But the question is, will you? Will you let me be your first?” I was still trying to wrap my mind around the fact that he wanted me, and I found if I thought about it, that I wanted him too; badly. I chewed my lip thoughtfully and finally nodded with confidence.
“Yes, Christian, I will.”
My response caused him to smile broadly and he leaned down to cup my face in his hands, bringing my face to meet his. He had always been pretty open about his sexual escapades and I had longed to be one of those girls for awhile. Tonight, my fantasy would finally be fulfilled.
He deftly stripped down to his birthday suit and climbed onto the bed beside me. Rolling over without a word he ran his hand through my hair then moved it down to cup my jaw. Once there, he used it to guide my face up to meet his as he kissed my lips tenderly.
I attempted to reign in my inner goddess’ sheer joy as she was currently dancing around a fire in her own reenactment of the guy from that Castoff movie. I brought my focus back to the kiss and allowed myself to be swept up in him and the sensations he was causing. He had begun to softly stroke the roof of my mouth with his tongue while pulling my hair into his fist, resulting in a soft tug. How did he know how these simple things would make my body react, we’d never really talked about this. My subconscious interrupted sharply. ‘That’s because he’s done this before you half wit. He’s good at this from plenty of practice, not because he knows you. Don’t be so naïve.’
I realized that she was right, of all of things that he and I shared with one another, the many adventures he’d had were definitely among those secrets. But I refused to let her derail me and I put in my proverbial ear plugs to shut her out then went back to focusing on him and the moment he’d caught my body into.
After nibbling on my bottom lip he began to nip his way from my lips to my jaw, then to my earlobe then from there he traveled down to my neck. When he grazed a particularly sensitive place my back bowed up against him, pulling my head back and in turn giving him more access to the exact part of my body that I’d apparently attempted to shield from his mouth’s tender assault. My hands wound their way through his hair and tugged firmly as the sensations grew stronger.
While he did keep one hand under my jaw, he allowed the other to roam down to my naked breast where it barely filled his palm.
I blushed embarrassed and murmured weakly, “I know they’re not very big…”
He paused and seemed to stare at me confused for a moment, “Allie, honey, what? These?” He gestured to his full hand, which squeezed lightly. “Oh no, don’t you even doubt for a second how perfect they are.” To emphasize his point, he leaned down and kissed the tip of my nipple lightly, eliciting a gasp and a moan from my lips. “You are beautiful, hun. Do not let anyone tell you any differently.”
I couldn’t help the smile that crept onto my lips, “Beautiful, you think so?”
He nodded and paused bringing his forehead to mine and staring deeply into my eyes. “Allie baby, you are you the most beautiful girl that I know; you’re gorgeous. Now shut up and let me make love to you.” I nodded weakly as he began to more fervently kiss my neck while his hand continued caressing my breast.
He fingers had begun to deftly travel along the tender flesh of my nipple, randomly pinching and tugging it lightly. He guided me back onto the pillows and he allowed his hand to travel further down, trailing the sensitive flesh between my breasts, down over my rib cage, the over my navel, pausing to circle lightly.
Every nerve ending inside of me was on fire and I squirmed beneath him wanting…needing, but not sure what for. His fingertips glided down over my stomach and down across my hip bones, then they continued downward. He passed my aching pussy and ran the pads of his fingers along my inner thighs, gripping the inside of my leg and pulling them open; teasing me. I could feel muscles that I had never known before tonight clench, taking my breath away.
Then he finally touched me, although he only allowed his fingertips to lightly graze my clitoris before moving away. My entire body shuddered and he smiled proudly. I could feel my molten core simply melt, vibrating on its own, who needed that toy anyway?
I then surprised him my reaching down between us and gripping his cock with a strong grip and I was surprised at what I found. While it was hard as it looked it was also smooth, like velvet. I stroked it squeezing him more heartily as I came up until he sucked in a breath, “Allie, honey, I’m not going to last long with you doing all that. You’re pretty damn good at it.”
I beamed with pride and he looked deep into my eyes, “Are you ready?”
My breath hitched but I nodded, “I’ve never been more ready.”
To my surprised he sat up and reclined back on the pillows. Only when he began to guide me over toward him did I stop him, confused. “What are you doing? You want me to sit on your lap?”
He chuckled, “Well sort of, I want you to come over here and sit down onto my cock. It’ll help make it easier for the first time, and not to mention it’ll feel even better this way.” I looked at him cautiously but his eyes radiated truth so I followed his lead. He helped me to position myself over his lap and holding his cock in one hand and with the other on my hip he began to guide me downward.I placed my hands on the tops of his shoulders for balance and continued moving down until I felt the tip of him pressing against me. I knew by looking at him that he would be big but feeling him there made it real how much bigger he was and I looked into his eyes, worried.
He looked back intently, “Do you trust me?”
I nodded softly and he smiled “Good, then just follow my lead. Let me guide you. Now take a deep breath… good girl.”
With that I felt him push upward against me slightly with his hips and he steadily guided my hips downward. I felt the tip breach my tiny slit filling me and I fought the urge to pull away.
Then he inhaled deeply, “Okay now the head is in, this is the tough part. I will make this as swift and painless as I can, don’t be afraid to make all of the noise you need to. You are so tight, this is not going to be easy, but you will enjoy it more after, okay?”
For a moment I sat, letting my nerves get the better of me until I realized that he was waiting on my answer.
“Oh, um, okay.” I croaked softly.
He gripped my hip more firmly moving the other hand to my opposite hip and pulled firmly downward, quickly forcing himself inside of me. In a moment I was overwhelmed by a flash of pain but I didn’t move, afraid to make it worse. He continued pushing until he filled me completely. I froze, tears stinging the back of my eyes.
He kissed me sweetly, “I know it hurts, hun it will start to get better, trust me.”
With that he began to move inside of me, at first I put my hands on his chest to stop him but he didn’t stop working me up and down in small increments. Tiny whimpers escaped my lips every few moments until the pain began to ebb. Eventually I found that I was the one moving, which drew a smile to his lips.
“Does that feel good, Allie?”
I nodded and closed my eyes as I moved atop him up and down, chewing my lip feverishly at the intensity of the sensation. I lifted myself up then quickly lowered myself down until my pubic bone met his and he completely filled me, stretching me out as far as I would go. I winced slightly but schooled my expression so it wouldn’t show, and he groaned.
“My God, Allie, you are so incredibly tight. I won’t be able to stay for long!”
I took that as my cue, and I began to work myself up and down on his cock milking him and squeezing him tightly as I lifted myself off of him only to lower my hips back down. I felt the familiar sensation growing in my belly and I found myself bouncing in his lap until I exploded, slamming myself down onto him. This caused a chain reaction where he erupted in his own orgasm, filling me with his seed as he pulled me to chest. I moaned, loud and uninhibited while he grunted with his release.
Once the high began to fade I felt as if my entire body were completely sapped of all of its energy. He carefully laid me down rolling over behind me and pulled my back against his chest, then he wrapped the blanket around us and kissed my hair as I mumbled an incoherent thank you.
“That was amazing, and you felt so tight! Good night Allie, rest well hun.”
My eyes drifted closed as I reveled in the warmth of his chest against my back. I had been thoroughly fucked and I couldn’t wait to see where this would lead us.