My Best Friend's V Day Massage

When she didn't tell me to stop I started to rub her firm ass in circles. Maybe if she wasn't into this sexually I could always say this was just a part of the massage. I cupped her ass and she let out a moan. I did it again and so did she. I couldn't believe it, this was finally happening. I spent the next couple of minutes enjoying the softness of her skin and panties. I experimented and found the touches that seemed to earn the loudest response from her. When I slid my hand down towards her other cheek I grazed the middle of her cheeks. She shifted into my hand and moaned louder. The angle was a little more awkward to touch her cheek that was against the bed. My palm would brush up against her inner cheeks and she would jolt against my hand.

I had left my right hand at the edge of her shorts, waiting to see if I could take things further. She started to grind her ass back against my hand, adding extra pressure and contact. There was a moment with each rotation of her hips that my fingers were almost inside of the front of her shorts. With each rotation, I would slide my hand deeper inside of her shorts. As my hand got closer she started to breath heavier and thrust back harder into my hand.

The last thrust lifted her shorts back so that they were nearly fully pulled back. I could see her black panties and half of what they held within. With my eyes locked on my goal, I crested my fingers up onto her panties. The texture of them acted like speed bumps or slicks of oil in the road. The see-through sections tickled against my skin. I could feel small sections of her skin and pubic hair through the mesh and I lingered at each of these sections. When I reached the silky gusset in the middle my fingers slid down towards her waiting pussy. My hand cupped her pussy and we both exhaled at the same time.

The fabric was damp with moisture and clung tightly to her pussy lips. I started at the bottom of her lips and ran my finger along the crease where they met. When my fingers reached the top, I rubbed against the nub of her clit. She jolted her hips forward at the contact. I moved my fingers back to the bottom of her pussy. I decided to experiment and do it again, only this time I pressed deeper into the fabric and slowly trailed my fingers upward. Her plump lips parted slightly as I pressed into her lips. When my fingers reached her clit this time I touched it with more than just a glancing caress. She rocked again against my hand at the contact.

So far, I had only been using only one hand as I pressed how far Violet was willing to go. I had been so focused on only pushing one boundary at a time. While I continued to rub her pussy and clit through her dampening panties I went back to rubbing her ass as well. I slid my hand inside of her panties through the side of her panties and started to cup her bare ass. Violet always had smooth skin, when I massaged her, I guess that included her ass too. Her skin was warm and smooth to the touch and I couldn't get enough of rubbing and cupping it.

Violet was breathing heavier and started to hump against my hand, driving my fingers as deep into the folds of her pussy lips as the panties would allow me. I pulled my hand away from her pussy and she let out a disappointed sigh. I didn't disappoint her long. I flipped the hem of the shorts up so that I could see her pussy better. The shorts were so open that now almost her entire pussy was displayed before me. I put my hand back on her upper thigh and slid it inside of her panties along the top and side of them. Her pubic hair was short and soft; the closer I got to her pussy the more her pubic hair became slick with her juices.

It was a bit of an awkward angle but I could reach her pussy from the side. I curled my fingers out and pressed down, sliding them in between her lips. I was still enjoying rubbing her ass but it was nothing compared to the feeling of sliding my fingers in between her lips. She was so wet that when I curled my fingers back to open her pussy my fingers lost their grip and slid free. I tried it again, this time pushing my fingers deeper into her folds before spreading them open. I saw hints of her pink pussy through some of the mesh design that surrounded the gusset. Between feeling how wet she was and getting a glance at her pussy my dick was throbbing against my pants. I wanted nothing more than to free it but I was afraid that if I stopped pleasuring her than the spell would be broken and the passion would flutter out like a candle in the wind.

I placed my fingers back in between her lips and slid them towards her entrance. I took a moment to rub the area around her entrance and then slid my ring finger inside of her. My ring finger found her entrance first. The heat radiating out from her pussy was a contrast to the cold air coming in through her open window. I slid the first digit of my ring finger inside of her. I had never felt a tighter pussy before. If it wasn't for how wet she was then I doubted I would have been able to get my finger in her at all. I knew she wasn't a virgin, but also that it had been almost a year since her last time having sex. Violet stopped thrusting against me, her chest rose and fell rapidly. I pushed more of my finger inside of her until about half of it was in. I paused for a few seconds, letting her get used to my finger inside of her, and getting used to all that was happening myself.

I curled my finger, pressing it along the sides of her inner pussy, causing her to shudder. I kept on probing the inside of her as far as I could. The angle and tightness of her made it harder to be able to move my finger around. I explored her pussy walls, remembering which touches caused a pleasurable reaction. I slid my finger back towards her entrance to where just my fingertip was inside of her and rubbed her clit with my thumb. When she exhaled at the contact I slid my finger back inside of her tight hole. Doing the two actions back to back caused her to interrupt her exhale with a moan.

While still fondling her ass with my other hand I alternated between working my finger in and out of her and rubbing her clit. She would rock her hips to meet my finger as I slid inside of her. Her wetness coated my hand, helping me be to slide deeper inside of her.

After a while, my hand started to cramp up from having to twist it to be able to reach inside of her. I was used to my hands cramping up from all the times I would massage her for hours at a time. I had always worked through the pain then, so I was confident that I could endure it now.

I played with her ass and pussy for an unknown time. All I know is that the movie changed scenes several times. I wasn't trying to get her to come right away, I was more than willing to take my time and figure out what she liked. I wondered if from now on this was how we would spend our nights together, me fingering her all night. I probably would still have to give her back massages so I made a note to look into hand stretches and exercises.

Violet rolled over onto her back, pulling free from my hands inside of her panties. I wondered for a moment if that was the end but then she spread her legs out for me. I pulled her shorts open and reached up to pull her panties to the. The top of her pussy was lightly coated in pubic hair. For some reason, I had always suspected that she kept her pubic hair well groomed. Seeing that I was right didn't take away from how sexy her pussy looked. I had always wondered what her pussy would look like, I would masturbate to pictures of her and try to envision how she would look with her pants off. Her pussy lips were plump, tight, and protruded slightly from her mons pubis.

I spread her lips out and stared into the pink folds of her inner lips and into her opening. The pink of her pussy made me think of pink rose petals. Moisture gathered at the bottom of her pussy and along her lips. I ran my finger along the bottom of her pussy to collect the moisture. I trailed my fingers from the bottom of her pussy and along the edges of her pussy lips in a circle. I completed another circle and then slid my finger inside of her. She inhaled sharply as I started to push my middle finger inside of her. She exhaled with a shudder when I had my entire finger in her.

I pulled my finger nearly all the way out and then slid it back in. I tried to finger her slowly. At first, I was helped by how tight her pussy was, but the more I fingered her the faster I went. The sounds of her arousal, my throbbing erection, and her increasing amounts of wetness spurred me on to go faster. Her pussy walls were still tight and hugged my finger, but now I could bottom out my finger with a light press, her vaginal muscles pushing and pulling on my finger.

Violet started to hump against my hand, urging me to go even faster. As her movements increased so did her breathing and the sound of her moans. The next time I pulled my finger out I added another one. It was a tighter fit but she was so wet and thrusting up against my hand so much that she took in both my fingers after I barely pushed in. She cried out when my fingers bottomed out inside of her. I continued to slide both fingers inside of her, trying to go deeper with each push.

Her thrusts started to intensify and she humped against my hand erratically, making it harder for me to nail down the rhythm. I gave up on trying to synchronize with her humping. I curled my fingers up and rubbed along the top of her pussy in a come-hither motion. She started to buck up against my hand, her lower body lifting from the bed. "Daniel," She cried out my name as her orgasm hit her body. Her tits were thrust up as her chest rapidly rose and fell. I stared at her large tits, the part of her body I had always fixated on the most. I didn't want this to end without touching them. As she humped against my hand I grabbed her tit with my other hand. The nub of her nipple pressed through the cotton of her shirt. I brushed it with my thumb and then cupped her breast. It was the biggest tit I had ever held and I couldn't fit it all of it in my hand.

When her orgasm ended she fell back into the bed. My fingers slid out of her but my hand still rested cupping her tit. I sat there, too stunned at what just happened to move. I felt the frantic beat of her heart as my hand rose and fell with each of her breaths. A few minutes later her breathing evened out and her heartbeat slowed down. "Daniel," She said my name again, this time in a wisp of a whisper, causing those feelings I had for her to flare up. A minute later she started to faintly snore.

My dick was straining for release. I still had my hand on her breast, her softening nipple pressed up against the palm of my hand. I wanted her so badly but didn't want to touch her if she was sleeping. I slowly crawled out of her bed and walked to her bathroom. She kept her hamper in there. I reached in and pulled out a pair of her panties that were dark blue and purple. I leaned against the wall next to the hamper and pulled my pants and boxers down. I inhaled the faint aroma of her pussy from off her panties. There wasn't much of a smell and then I thought about my fingers. I sniffed them, the smell of Violet's pussy was stronger than any other girl that I had been with, it was a nice mix of musk and sweetness. Strong and sweet, her pussy matched her personality.

I wrapped the panties around my shaft and started to stroke. The smoothness of the panties combined with the fact that I just fingered Violet had me close to cumming after a minute. I closed my eyes and imagined that the tight silkiness wrapped around my shaft was me inside of my best friend and not just her panties. The thoughts of her looking up at me with her beautiful eyes while I plunge inside of her, of her riding on top of me with her tits bouncing with each thrust, or of me taking her from behind with her toned ass sticking up into the air put me over the edge. I grunted and then started to cum. I wrapped the panties around my head to contain the mess. Spurt after spurt of cum shot out of my dick and coated the panties. If there had ever been a time where I came more I couldn't remember it.

My orgasm seemed to take all my energy out of me and I had to lean forward to support myself on the wall. I rinsed the panties out in the sink and put them back where I found them. I was exhausted and barely made it back to her bed. I climbed back up into her bed and fell asleep on top of the pile of clothes.

I woke up in the middle of the night and Violet wasn't in the bed. She usually woke up before me but the sun wasn't out yet and this was too early, even for her. I walked down the hall to the living room and saw that she was sleeping on the couch. She had done this a couple of times before and it always confused me. I wondered if she was ok but wasn't about to face her wrath by waking her up. I went back to her bed and laid in her spot on the bed. The clean floral scent of her shampoo on her pillow was the last thing my brain processed before I fell asleep.

I woke up to the sounds her getting ready for work. I tried to cling to my sleep but couldn't. I could always fall asleep easily and was a deep sleeper, but once I woke up for the day it appeared the gates to the realm of sleep were slammed and locked behind me. I burrowed under the blankets and rattled against the gate as I tried to fall back to sleep.

"Wake up, we have to leave soon," Violet said. When I didn't get up there was a soft thud as something landed on top of my head. Even buried under the blankets she had managed to aim and throw a pillow perfectly at my head. I sat up immediately. The ongoing joke was that first she would throw a pillow at me, and if I didn't get up then it would be something more solid. We never got to the second mystery object, I hoped she was joking, but I wasn't about to test it.

By the time I put on my shoes and used the restroom Violet was ready to go and she told me to come on. We got in the car and she started driving me home. When we stopped at one of her favorite to go coffee shops, I wasn't surprised, she always made time for coffee.

I kept on glancing at Violet out of the corner of my eyes. She seemed to be ok, but I was also picking up a vibe that something was wrong. In all my fantasies of hooking up with her for the first time, I never really thought about the morning after. Sure, I thought about how after us hooking up it might lead to a friends with benefits situation or hopefully us dating, but I didn't know what I expected the morning after to be like. Something seemed off but I couldn't pinpoint why I felt that way.

The ride from her apartment to mine wasn't long which was both a blessing and a curse. I wasn't sure if anything was wrong and if I had more time with her I could figure it out, but when Violet was upset about something she would get quiet and say something eventually. Asking her about it would do no good. She pulled into my apartment complex and parked in front of my building. "Thanks for the ride home," I said.

"You're welcome, thanks for hanging out with me."

I leaned over and gave her a hug. She felt stiff in my arms so I pulled away. "Have a good day at work," I said as I climbed out of the car. I watched her drive away and then went inside.

I bounced inside so happy that I finally got to really spend the night with the girl of my dreams. I had taken a chance and it paid off. I walked into my room and changed out of my work clothes. Snapshots of what happened last night flashed through my mind. At the thoughts of her spread pussy and the feel of my fingers inside of her, I started to get hard.

I laid down on my bed in just my boxers and started to slowly stroke myself. Today was my first day off and I didn't have anything planned so I was going to spend most of my day relaxing. I took my time, slowly running my hand up and down my shaft. Even though I had a coffee I was still tired and I would start to drift off to sleep, only to wake back up and start masturbating again. I sniffed the fingers that had been inside of her, I could still smell her strong aroma clinging to my fingers.

I must have been on and off again masturbating and napping for almost an hour. I was finally getting close to cumming when my phone chimed with a message. It was from Violet and when I read it I stopped jerking off. "What happened last night was a mistake. I was close to falling asleep when it started and I don't like that fact. I am hurt that this happened and I'm going to need some time to get over it. Give me some space and let's pretend like what happened never did."

I read and reread the message. I had thought she was fully awake last night, otherwise I would have never touched her like that. I thought of her opening her legs for me and the sounds of her moans. I thought of how she had said my name right after she came. I thought she was awake!

During our friendship Violet had revealed a lot of dark personal stuff to me. She had been taken advantage of numerous times by guys who coerced her into sex or borderline raped her. I had always felt revolted by anyone taking advantage of someone who was so kind-hearted. Now I was another one of those guys who took advantage of her.

I felt horrible and hated myself for what I did. I stayed in bed most of the day, alternating between sleeping and staring at Violet's message trying to find the right thing to say to her. Violet was my closest friend who was always there for me, and now I did something that could ruin our friendship. I didn't get out of bed until five pm. I floated from room to room, not really knowing what to do with myself. I tried watching tv and playing some video games to distract myself but I couldn't get into them. I kept on thinking about what I did and how hurt Violet must be feeling right now.

When it was close to 10 pm I decided to try and sleep. I lay in bed, trying to not think about what happened, but the more I tried not to think about it the more I did think about it. I pulled my phone out and read the message again and then scrolled through our conversation log. Seeing our ongoing jokes and all the time we said we loved each other put a new edge on the pain, but it also gave me hope. She could have told me she never wanted to see me again, instead she told me to give her time. When I have a problem, I throw myself at it to try and solve it. I knew this wasn't something I could fix just because I want it to be fixed.

I set my phone down and tried to sleep for an hour but couldn't. I turned back on my phone and opened the find my friend app. When Violet set it to where we could see each other's locations at any time I was a little weirded out, but not enough to tell her no. It had come in handy often when she would see if I was at work and ask if I wanted a ride home. It showed that she was at home, probably in bed by now. Picturing her sleeping and relaxed calmed me down and I was finally able to drift off to sleep.

The next couple of weeks were rough for me. After a couple of days, I had tried to ask Violet if she wanted to hang out. She told me that she wasn't ready to see me yet. I had hoped enough time had passed but I was wrong.

I would see her posts and updates on Facebook and Instagram. She seemed so happy without me in her life. Seeing her smile made me think that maybe she was over what had happened, but if so then why hadn't she texted me?

It was February 13th, twelve days since the last time I was with Violet. I had started to make peace with the fact that Violet was out of my life. I may have been overreacting, but we hadn't gone this long without talking in years.

I was doing some reading for school when my phone chimed. I glanced at the screen and when I saw that Violet had messaged me, I snatched my phone off my charger. "Hey, are we still on for tomorrow?" Her message seemed so normal and out of place after nearly two weeks of silence.