Two Best Friends Cross a Line

Lynn and I have been best friends for as long as I can remember. His mom and mine were friends from the beginning of elementary school and we always spend time together. We still do actually.

We never had any thoughts about going any further than just being friends, even if literally everyone around us thought we were a couple. I never saw her that way. Yes: I knew she was attractive, but she was just my buddy. Nothing more.

When we were little we used to go on holidays together with our parents. We always had the best of times. Once we went to high school we never stopped imagining what it would be like if we went to the same university to live together in the dormitories. We did actually for the first two years of college, then we started to get sick of the fact that we always had roommates around or that it was quite small. We then decided to take our friendship to the next level and rent an apartment off-campus. It was the best decision I've ever made.

People around me thought it might be weird, living with a girl who is not my girlfriend, but I could only see the benefits. Lynn was an excellent cook, which made dinner quite easy for me. She had a lot of dance practice during the week and on the weekends so there were more than enough hours for me to spend on me time or to invite my friends. Also, if I wanted to hang out with Lynn, I just had to walk into the living room and there she was.

There were quite some difficulties tho. Especially when it comes to bringing girls or boys home. I wasn't the type to fool around with multiple people but Lynn definitely was. I always made them pancakes in the morning - usually I was making them for myself and it would have been rude not to make some for them - but I always felt quite uncomfortable with it.

One night I came home from a late class. I opened the front door, put my bag on the floor and kicked my shoes off. It smelled amazing. I looked over to the kitchen and noticed Lynn was cooking a homemade meal.

'Hey' I said whilst I walked into the kitchen. Lynn looked up and smiled at me. 'Hi. I'm making pasta. You hungry?'

I nodded. 'Imma go change.'

I walked into my room and decided it was just time for me to change, I also wanted to take a quick shower and wash off the busy day I just had. I looked for my pair of loose joggings in my closet and decided on a big oversized hoodie. I walked into the bathroom and threw my clothes in the laundry basket. I put on the shower and whilst waiting for it to get hot, I checked myself out in the mirror.

My body is not that bad but also not amazing. I work out a few times a week so I am comfortable in my own skin but I'm not a stud or anything. Lynn always tells me otherwise. She always tells me how handsome I look and how I should not be this insecure about myself. I just can't help it. Maybe the fact that I don't have much experience with girls doesn't help me with my insecurities.

As I was just about to step into the hot shower, the bathroom door opened. I stood frozen and I did not know how to act. I noticed how Lynn stood in the doorway also completely frozen. I followed her eyes, who were gazing at my dick. When I realized what had happened, I put my hands in front of my dick so that she wasn't able to see it anymore.

'Oh my god' Lynn said. 'I am so sorry. I did not know you were in here' she mumbled as she closed the door and walked away. I was not sure how to act, should I go after her or not say a word? I decided to just hop in the shower and try to act like that didn't happen at all.

Ofcourse, when I was in the shower, my mind wandered about what just happened. Even though Lynn and I have been very close for many years, we had never seen each other naked. Now that she has seen me naked I wondered what she thought of me. I felt my insecurities kick in and found me asking myself if she'd like what she saw or not.

I dried myself off - ignoring the fact that my dick got a little hard thinking about Lynn seeing me naked - and got clothed. I walked into the kitchen like nothing had happened. Lynn sat at the kitchen table with dinner ready and two glasses of wine next to it.

'Smells great,' I said. Lynn just smiled at me. I tried to guess how she felt by looking at her face but I could not tell. She either was not uncomfortable at all or was great at hiding it.

Dinner was not weird at all. We talked about our day and laughed, like we always do when we eat together. Nothing special. I decided to let it go and not think about what happened before anymore.

Later that night, when I was chilling in my bedroom, I heard a slight knock on my door. 'Yes' I answered. Lynn opened the door with a smile. 'It's the weekend' she said. 'I bought some beer, thinking we could like, play games or something.'

'Sure' I said whilst putting my playstation to rest. I went to the living room with Lynn and we played board games all night. The last time I checked the time it had been 9:30, right now it was almost 2:00. We played millions of board games and finished a whole lot of beer.

'Why do you always win?' Lynn said with a pout on her face while she put the game back into the closet. I sat down on the couch and laid my feet on the coffee table.

'Because I'm the best' I said with a smirk. Lynn said down next to me and gave me a playful push. I laughed at her. She sat next to me and laid her head on my shoulder. I wrapped my arm around her.

'Sam?' she said quietly. I nodded.

'I don't want it to be awkward between us after I saw your dick.'

I laughed at the way she expressed herself. Lynn had never been subtle but sometimes when she said something I couldn't help but laugh. 'No, I am serious' she said.

'But why are you so ashamed of your body?' she suddenly asked me. I was shook by this question and felt quite uncomfortable.

'Ehh' I stammered. 'Why do you ask?'

'Because you're handsome.'

'You always say that. Do you really mean that?'

Lynn looked up at me and smiled. 'Of course, why else would I say it?'

I shrugged my shoulders. 'To make me feel better?'

'If I just wanted to make you feel better I'd do some whole other things to you' Lynn said with a smirk on her face. I gave her a playful push and she laughed. 'You with your sex jokes' I said.

'About that, how are the girls? Are you getting any action?'

'I don't wanna talk about that' I said and I took a sip of my beer. Lynn loosened herself from me and sat straight up next to me. She looked me in the eye. 'Why not?'

'Because I have a pathetic sexlife.'

'I bet you don't. When is the last time you had sex?' she asked.

I felt my cheeks getting red. I do not want her to think of me as a loser so I hated this topic. 'When I was with Claudia' I said shyly. Lynn's eyes got big. 'But that's like.. A year ago.'

'I know' I said. I felt uncomfortable.

'And when's the last time someone touched your dick? Or that you kissed someone?'

'Lynn..' I said, trying to make her stop this conversation. I felt stupid. She did not respond and looked at me hopefully, waiting for a reaction. 'Also Claudia.'

'So you haven't done anything with a girl in a year? Don't you miss it? Aren't you like.. horny all the time?'

I felt my cheeks get even more red - if that's even possible. 'Yea..' I mumbled.

Before I knew it, Lynn pushed her lips against mine and started kissing me. I did not know what to do or how to react. Why was she doing this?

'Lynn, what are you doing?' I mumbled against her lips.

'Just go with it' she said. She kissed me again. This time I let it happen. I felt her soft lips on mine and I kissed her back. First without tongue but soon enough she slipped hers into my mouth. She was a great kisser actually. As our tongues were intertwined I wondered how this was the first time we had ever kissed and why it had never happened before.

She crawled onto my lap, one leg at each side, and kissed me with even more passion. Her hands were on my shoulders and mine were on her back. She grabbed my hands and lowered them on her body, onto her ass. She laid my hands there and put her own hands on my chest. My hands grabbed her ass firmly as I kept kissing her.

I immediately felt my dick grow in my pants. I assumed Lynn felt it too, because she started to grind on me.

What the fuck were we doing? Is this okay? In all those years of friendship we had never done anything like this and I did not know what I thought about it. How I felt about it was made perfectly clear in my pants.

Lynn broke our kiss and looked at me. She scooted herself backwards a little on my lap and laid her hand on my grown. I let out a soft moan as she did this.

'Lynn..' I said. She stopped me by kissing me again. Whilst she kissed me with that amazing tongue of hers, she pulled my pants down - which wasn't easy with her still on top of me. The only thing standing in the way between my dick and the air was my pair of boxers.

She broke our kiss again and leaned backwards a little. She pulled her top over her head and unclasped her bra, which released her boobs right in front of my face. I stared in awe at them. That Lynn was beautiful was not new to me, I had always known that. Being a guy I of course had always noticed that she had amazing boobs. I just had never seen them naked. And here they were, in front of me. I immediately took one in my mouth and sucked on her nipple. Lynn moaned, the sound which made me even hornier than I already was.

As I put the other boob in my mouth, Lynn pulled my hair. Her breasts were not small but not big either: a perfect size for me. I loved them. My hands moved to her shorts, which I unzipped and pulled down. She stood up and released herself from them, along with her panties. There she stood in front of me: butt naked.

She crawled into my lap again and kissed me. I started to feel her down there with my fingers, slowly massaging her clit. I saw how her eyes rolled back when I did this: what made me even hornier. By now my cock almost jumped out of my boxers.

I put two fingers inside her wet pussy and Lynn moaned. 'Fuck, Sam.'

Her saying my name like that was it for me. I pushed her off of me and laid her on the couch als I started fingering her real hard.

'Holy shit' she practically screamed as I kissed her again. She moaned against my lips, which was so sexy I almost wasn't able to keep it together.

I suddenly felt her body tremble as she moaned my name again. 'Fuck Sam, you're gonna make me come!'

Her mouth created a perfectly rounded 'o' as her body was shaking under me. Her eyes rolled back and she moaned as loud as she could.

It was one of the hottest things I had ever seen.

'Fuck Sam' she said as she was finished. I sat up on the couch and Lynn sat next to me. 'That was amazing.'

'But'

I suddenly felt insecure. Didn't I do it right?

'I actually wanted to make yóú feel better, this was not supposed to be about me' she said whilst putting her hand on my groin again. I moaned as I looked at her. She smiled back at me and her eyes were sparkling. She then suddenly grabbed under my boxers, grabbed my dick and pulled it out.

Her touching my dick felt amazing. Nobody else had touched this dick in over a year but me and when she did, I realized how much I had missed it. Lynn started slowly stroking my cock as I looked at her. She bit on her bottom lip.

'Fuck Sam, who knew you had such a big dick?'

I felt my body tremble as she said those words. Who knew she was such a dirty girl?

'I kinda wanna taste it' she said, licking her bottom lip. Before I could respond, she had bend down and licked the mushroom tip.

'Holy shit' I whispered. She cupped my balls with one hand whilst the other was still pumping my dick. She started sucking the top. It created a sensational feeling.

'Holy shit Lynn you are so good at that.'

I noticed how she smiled whilst sucking me. I let my back fall down into the couch and enjoyed the view: this amazing, beautiful woman in between my legs, sucking my cocks and playing with my balls.

Before I knew it she deepthroated the shit out of me. I had never felt anything like that: my ex was not able to deepthroat. Lynn did it without any hesitation. It was the hottest thing I had ever seen and felt.

'Holy fuck, if you keep doing that, you're gonna make me cum' I said. Lynn smiled at me and took my whole dick inside her mouth: again. She sucked and made long strokes with her mouth, continuing to take it deep into her throat. I felt a sensational feeling coming up from my balls as she did that.

'Fuck I'm gonna come' I said. Lynn sped up her rhythm as I said that, which made me believe she wánted me to come. That did it for me and I let it all go. I put my hand onto her head and pushed it down as I felt an amazing sensation hitting me. Lynn looked up at me with her bright eyes whilst I was cumming all into her mouth.

'Fuuuuck' I said while I was still cumming. It was the most I had cummed for months and it felt amazing. Once I was done coming, Lynn swallowed and let go of my dick. She stood up, grabbed her clothes and walked away.

'Goodnight' she said with a smile, and she closed her bedroom door, leaving me completely in shock on the couch.

-----

It had been a month since Lynn had sucked my dick and we never spoke a word of it again. Our bond hadn't changed since that night: we just pretended like it never happened. To be honest I didn't quite know how to react to her the morning after, but she just acted like nothing had happened, so I just went along with it.

It was a wednesday evening and I was home alone. Lynn had dance practice which led to me ordering pizza and watching tv all night on my own. It was around 11 PM when Lynn still hadn't come home and I started to get a little tired. Normally I waited for her to come home so I knew she was home safe but I was just so tired that I decided to go to bed.

I woke up because I heard noises in the living room. I checked my alarm, which told me it was 2:30 AM. I figured it was Lynn and tried to go back to sleep. The noises kept coming and I wondered if Lynn was okay. I put on a pair of sweatpants - I only sleep in my boxers - and walked into the living room. It was dark but I saw a light coming from the kitchen. When I walked in there, I saw Lynn drinking a glass of water.

'Hey' I said. She turned around and I immediately could tell she was not okay. Her eyes were bloodshot and her face was wet with tears. Without saying anything I walked up to her and gave her a hug. She immediately gave in and hugged me tight. She cried on my shoulder for a while before I asked her what had happened.

'I failed my exam, which resulted in me having a massive fight with my mom' she said. Her mom was always super harsh on her: she wanted Lynn to only get A's or B's and was kinda mean to her when she didn't get any of those things.

'She said horrible things to me on the phone and I felt awful, so I put out my phone and started walking through the park' she sobbed. 'Then my phone died and I did not know where I was so I spent two hours trying to find my way home and here I am.'

She unleashed herself from my hug and finished her water.

'I don't know what to say' I said. 'I'm sorry that you and your mom are always fighting. What kind of things did she say?'

'She called me a screw-up.'

'Lynn, you are many things, but you are not a screw-up.'

She smiled at me. 'I'm sorry that I stayed away from home that long. I'm gonna take a shower. Thanks for listening to me.'

She gave a quick kiss on my cheek and left the kitchen. I walked into my bedroom and heard the shower running. I kicked off my sweatpants and got into bed. Not long after I heard a soft knock on my door. Lynn opened it and walked up to my bed. She was wearing nothing but an oversized t-shirt I gave her once.

'This is a weird question, but can I maybe sleep here tonight? I kinda don't wanna be alone.'

It was dark so I could not see her facial expression very well, but I also knew that when Lynn asked for anything, she really needed it. She never asked for help.

'Of Course' I said. She crawled into my bed and laid next to me. I put my arm around her and she snuggled up against me. I felt her wiggling against my dick for a second, which of course resulted in it getting hard, but I tried to ignore it.

We laid there like that for a while and it felt nice. Lynn was the one to break the silence.

'Sam?' she asked.

'Uhuh?'

'Why didn't we ever talk about that night?'

I immediately knew what night she was referring to but I wanted her to say it. 'What night?'

'You know.. The night I..' She sighed. 'Sucked your dick.'

I chuckled. 'I don't know. What do you wanna say about it?' I asked.

I felt Lynn moving closer to me and wiggling against my dick again. Was she doing this on purpose?

'I liked it' she said, surprising me with her words. 'Me too' I answered. She laughed.

We lied there still for a while again until I felt her fingertip brush over my dick through my boxers. I gasped a little but did not say a word, which invited Lynn to go further. She grabbed my dick through my boxers and started subtly jacking it off.

No one said a word, we just laid there in the dark in the middle of the night, Lynn jerking me off. She then pulled it out of my boxers, made her fingertip a little bit wet and slowly brushed against the mushroom tip.

'Fuck that's sensitive' I said. Lynn chuckled and continued doing it, which made me even hornier than I already was. 'How come you are so hard?' she asked

'It's not every day that a hot girl is touching my dick' I said with a smile. Lynn looked up at me. In the dark I could see the sparkling of her eyes very clear. 'You think I'm hot?'

'Of course' I answered.

She smiled and before I knew it, she kissed me again. This time I couldn't take it anymore. All the teasing, the slow touches. I wanted her, I needed her.

I pushed her on her back and layed on top of her, which made her jerk away her hand from my dick. She opened her legs and put her hands on my back. I kissed her, with tongue. She was mine and I was hers. I felt my dick against her pussy and I slowly started grinding. The only thing standing in the way being her panties.

I grabbed her boob through her shirt and felt she wasn't wearing a bra. I put her nipple between my two fingers and started rubbing it. 'Holy shit' Lynn moaned against my mouth. She pulled up her shirt and tossed it over her head. She then lied down again and kissed me. One hand in my hair, pulling it, making me want her even more.

I put my hand inside her panties and felt her pussy.

'Fuck, you are so wet for me' I said as I felt it. The minute I said it I wondered if it was too much of a dirty comment to make. Lynn smiled. 'I've always been wet for you, you just never saw it.'

Her comment pushed me over the edge and made me put two fingers all at once inside her pussy. She moaned my name real hard and arched her back while I did. Her free hand grabbed my dick and started jacking it off.

I started fingering her harder, which resulted in her recreating the tempo I did on my dick. I moaned. 'Fuck, Lynn, you are so hot.'

She pulled down her panties and I laid on top of her again. I pushed my mushroom top against her clit and slowly moved it. Her wet pussy made me glide smoothly all over it.

'Sam' she moaned. 'Fuck right there.'

I continued rubbing her clit with my dick until I couldn't take it any longer. I slowly slid my dick inside her as our eyes were locked. Her eyes rolled back into her head as she felt my dick entering her pussy. It felt so fucking wet, warm and tight: it was one of the best things I had ever felt. I slowly started moving and felt her amazing tight pussy around my cock.

'Fuck, you're tight' I said.

'You're big' she answered. We smiled at each other briefly before our faces turned into pure sex again. Her eyes stood horny as fuck and her mouth moaned my name and many 'fucks' and 'oh's' as I slowly pumped into her.