Our first time [MF]

Before I start this story, I wanted to say thankyou for all the kind feedback on my last few posts. I really enjoy writing these and the fact so many of you enjoy reading them makes it even better!

Check my profile for my others stories.

I’m going to save some of the more wild and hot stories for another time and write about a more personal and sensual story this time, I want to talk about all my experiences on here, not just the crazy ones.

This was very very early in my relationship with Mary, we had only done a very small amount of stuff and it was all her doing thing to me, I hadn’t even seen her naked yet.

We were at her house and watching friends on netflix, the one with all the poker I can strangely remember, I was in my normal attire. Just a plain white tee, and comfy tracksuit shorts. Mary was in jogger shorts and had a tank top with a bra on underneath. We were cuddling and getting comfortable. Mary had her head resting on my chest and I could smell her hair, it smelt of whatever shampoo she used, it was coconutty. I rested my arm on her side and put my hand just above her ass, on her trouser line.

After sitting like this I got the courage to slip my fingers under her shorts. I did it and she didn’t stop me. However it was only about 15 seconds later she stopped cuddling me and sat up, sitting across me. She lowered her laptop screen down and I could tell from how she was looking at me she was nervous.

“Is everything ok?” I asked.

“There’s something I want to talk to you about” Mary replied.

My heart sank, was she breaking up with me? Had I gone too far? Did I make her uncomfortable?

“I really like you” Mary followed up, I was still tense, the way she said it made it sound like she was going to follow up with a ‘but’.

“And I want to open up to you, there’s some stuff about me I haven’t told you because I’m worried you’ll not like me anymore if I tell you.” She said

“Hey, Mary” I said as I held her hands “I really like you too, if you want to talk, I want to listen to you”

She became visibly less tense, however I was still a bag of nerves, I wasn’t sure what was coming.

“Before I met you, something happened to me”

For personal reasons, I don’t want to go into detail here. Mary told me how she was sexually assaulted before I met her and how she was really finding it difficult to open herself up for me. We hugged and we cried, we watched more friends and laughed, of course my opinion of her hadn’t changed. If anything I held her in a higher regard and she was battling something and she opened up to me. We grew closer and I knew that I wanted to help her in anyway I could.

A few days passed and it was the weekend, I was back at her house. We had dinner, sat with her family and watched some TV before heading upstairs.

We walked to her room and I sat down on the bed, she came in after me and closed the door.

“I want to show you something” she said.

“Of course, what is it?” I replied

She put her hands to waist and grabbed the sides of her shirt, she lifted it up and over head. She revealed her bra to me, it was a sexy black lacey piece. It really looked good on her.

“Wow, I -” I was speechless, I couldn’t say anything, before my brain got into gear, Mary unbuttoned her jeans, she put her hand to her side and pushed her jeans to the floor with a little wiggle of the hips to help them down.

She was standing infront of me in just her underwear. This was a big moment for her and I could tell. I reached out and held her hand, and pulled her closer to me. We hugged and embraced one another. We kissed and my hands explored her half naked body. I ran my hands from her shoulders, down her back and sides and to her ass. I gently squeezed her cheeks. My god, it was at this point I knew I was an ass man. She stood back from me slightly and took off my top which she threw on a heap with her clothes.

She came closer to me again and I reached once more for her booty. I couldn’t get over how amazing it was to feel her. We kissed some more and I fell backwards onto her bed, she stayed on top of me as I fell. This brought her tits right onto my chest, they were weighing down on me in her sexy black bra. She eventually sat up.

“After our talk the other day, I know I want this. I really fucking like you, I know I can trust you. I’m so happy you were patient with me, without even knowing you proved to me that this actually means something to you” she said. She reached back and unhooked her bra. Her straps slid down her arms and she revealed her tits to me. They were the most amazing thing I’ve ever seen, we smiled at one another as she grabbed my hand and placed them over her boobs. I gently squeezed them, and she nervously giggled at me.

“It looks like you like what you see” she said

“I could go blind right now and be happy forever” I replied. We kissed some more before she made her way down to my trousers. She loosened them and pulled them down. Obviously I was absolutely rock hard, she had given me head before, but it was always in the dark and she didn’t want me to watch. But now I could see her doing everything. She worked my shift with her hands as she licked around my head with her tongue. She took me all inside her mouth and out again. This was 20x better than anything she had done before. I don’t know if it was just the fact I could see her or if she changed her technique. But this was amazing. She kept going and going and I was never going to stop her.

However she did eventually stop. She rose up from my lap and kissed me before standing up. Slowly she started pulling her panties down, she had clearly just shaved as it was all smooth until I saw her pussy. She dropped her panties to floor and stood infront of me completely naked. I could see she was slightly trembling.

“Wow, Mary, I don’t know what to say. You’re incredible!” I said

I held her hands and she was still shaking.

“I will follow your lead” I said “we can take this at any pace you’re happy with” with each word i could feel her relax more and more. She sat next to me and we kissed.

I placed my hand on her knee and she did the same to me. She made the first move and starting sliding her hand up my thigh, I followed suit and did the same. She reached the top of my thigh as I reached hers. She grabbed hold of my cock and I moved my hand across the face of her vagina.

She started slowly stroking me and I gently rubbed outside her pussy, she was wet. Not massively, but enough that it was smooth as I rubbed her. I found her clit and rubbed that too, going in a figure of 8 movement around her clit and around her vagina.

I was new to this and was doing my best to remember what every fingering guide I had ever read told me. Everything I had read flew out the window and I got in the moment. I did what felt right and it seemed to work. Mary quietly moaned as she started to jerk me off faster. The whole time were kissing, until I stopped and kissed her on the neck. I could feel her reaction to that through my fingers as I felt her whole pussy skip a heartbeat.

“I want you to go inside me” she said.

I nodded and without wasting a second I slid my middle finger into her. She tensed up and grabbed my arm. I thought she was going top rip it from my body. As I carefully pulled my finger out she eased up and let out a sigh

“Are you OK?” I asked.

“Yeah, I am, I think I am” she replied.

“If anything gets too overwhelming or if you want to stop, just tell me and we can” i told her.

She smiled and relaxed again. I slid my finger slowly into her again and this time she was a lot more calmer. My arm was safe. We sat and used our hands to pleasure each other for a good 10 minutes before Mary said “you can stop now, that was really nice thankyou. But I want to put my clothes on again” of course I stopped and she put her underwear back on. I grabbed to put my boxers back on and she stopped me.

“Just because I’ve had enough, doesn’t mean you have” she said. “I want you to finish, show me how you get yourself off” without wasting a moment I masturbated for her until I came.

We spent the rest of the evening cuddling in our underwear watching friends until I had to go home.

A week passed and in that time I had fingered her again. This time getting her to orgasm with the help of her guidance and techniques.

The weekend came and it was the same as the week before, dinner, TV with her family and finally we got upstairs to her room.

It started the same as it did the week before. Before I even sat on the bed Mary had got into her underwear. I took off my top and we kissed. Rubbing our hands over each other as we made out. We both got naked and I started to finger her again. After like 5 minutes she got up and walked over to her desk. She opened her bottom draw and got out a box of condoms.

She walked back over to the bed and told me that she didn’t want to rely on me bringing my own, and as she wasn’t on birth control didn’t want to risk it. She had clearly planned this moment in her head and she knew what she wanted to do.

I laid back as she rolled the condom down my cock. This was the first time I had ever worn one and it was pretty tight. I adjusted it slightly so it sat better on me. Mary laid down on her back and opened her legs for me. I propped my self up above her and got ready to go in. Both of our virginities were about to go with a single thrust. I found her opening and slowly started to push.

It was no good, she wasn’t wet enough and it was too dry to push in. Mary spat on her hands and rubbed herself, trying to get herself wet enough for me to enter. I tried again and it was still no good, I managed to get most of my head in, but it was obviously not enough. Once again Mary spat on her hands and rubbed herself. I used my head to spread her saliva around her pussy, pushed in once more and still had no luck.

“Maybe you can try” she told me as she stuck her tongue out at me to indicate what she meant. I understood and shuffled backwards, lowering my head in between her thighs. I used my fingers to warm her up, spreading what natural lube there was around her opening before slipping in 2 fingers, they went in reasonably fine and I pulled them out again. I lowered my head again until my mouth was at her clit. I opened up and got my first ever mouth full of pussy. As I licked up and around her clit I felt a wave of pleasure flow through her, already she was wetter than she had been before. I slipped in my fingers a few more times until I was happy it was wet enough, using my tongue the whole time to stimulate her clit.

I got back up onto my knees and repositioned my cock above her vagina. Once again I used my head to spread her now 10x wetter pussy apart. I pushed and got my head in no problem, however with every extra inch I got inside, more and more dry condom soaked up what wetness she had. I got about three quarters of the way in before I realised it wasn’t wet enough to go the whole way. But that didn’t matter. I was inside her, I felt her pussy squeeze my cock. We looked at each other and both of us had a smile on our face. That was it. We were no longer virgins and neither of us could be any happier. I slowly exited and re entered her, using what small amount of her cum there was to make it as smooth as possible.

It was probably only a couple of minutes before we decided to stop. I took off my condom and Mary used her hands to make me cum again. This time, I returned the favour and couldn’t wait to use my tongue to help Mary orgasm, I went down on her once more and with her help I got her to cum too.

We laid down and spooned completely naked.

“John, you’ll never know how much this moment means to me” Mary said. She had a tear in her eye.

“I’m so glad we did this together” i replied “There’s not any other way I would have wanted this to go”

Eventually I had to leave and I got dressed and did so. We decided we had to get some lube to help us, I ordered some off amazon and the following weekend we did it again. The lube made a big big difference and everything went a lot smoother.

Throughout our relationship, Mary got a lot more confidence about herself, along with some therapy I helped her get into, she made the right steps to getting over what had happened to her and we really explored a lot together. With the stories I’ve already told and with the stories I still want to write, you can see that our relationship went to places that a lot don’t and it was all because Mary had the confidence to push herself into trying new things and trusting me to be patient with her.

This is probably different to a lot of stories on here, but it’s one I really wanted to tell. If I look back on my relationship with Mary its always the one that makes me smile no matter what. I really hoped you enjoyed reading, even if it was different to my other stuff.

Don’t worry, I’ve got another story coming soon involving her friends again so stay tuned!

Source: reddit.com/r/gonewildstories/comments/p82vxn/our_first_time_mf