[MF] Giving my friend her “firsts” (Part 1)

Mary had been trying to flirt with me for over a year now. I had decided to play dumb instead of making an issue over it. It was easier to just pretend I didn’t get what she meant or deflect the topic entirely. I didn’t want to make things awkward. I’d known her when we were both much younger and we’d only reconnected a few years earlier. But she was good at flirting subtly, I’d learned since we started talking again. The subtlety made it easy to ignore.

But that changed one summer. I couldn’t just ignore it. She decided to me perfectly blunt with me, and I returned the favour. She told me that she’d had a crush on me for as long as she can remember. Even though we hadn’t spoken in many years, we ended up with a lot of the same interests and hobbies. I don’t know how much of that was natural or how much of it was trying to emulate me. Either way, that’s how it turned out.

I had explained to her that I didn’t feel the same way. There was a fair age gap between us and at the time that would make it impossible for us to be together.

But she tried again. Days after her 18th birthday. She told me that she was a kissless virgin and had wanted to change that for a while but never had the chance. She made me an offer I couldn’t really refuse. She wanted someone she cared about to be her first. She wanted that person to be me. Even if I didn’t want a relationship with her, she wanted me to ease her into the world of sex. I took a day to mull the idea over before giving her my answer. I’d do it.

At this point she had just turned 18 and I had just turned 29. That’s what I meant earlier about the age gap. But this was what she wanted. We both went in knowing the ground rules and accepting them. So, overall, I felt pretty good about this.

Mary had been to visit my apartment once before, when she was looking at colleges in the area and needed a couch to crash on for the night. But this visit was different. I knew she’d be nervous and that she wanted to take it slowly still. So I did my best to accommodate.

-NIGHT 1-

“I’m here,” she texted me from her car as she parked by my apartment building. I went down and let her in and we walked in silence to my apartment. I let her in and she sat down on the couch.

We gave each other a fairly normal greeting before I grabbed us each something to drink and sat down beside her. I could see her shaking from the nerves but trying to me happy and positive. I put on a movie for us to watch, partly to try and break the awkwardness, partly to help her calm down a bit.

I paid attention to the movie, mostly. But I could see she wasn’t. I kept seeing her look nervously over at me before turning back to the movie. I think she spent more time looking at me than she did at the TV.

About midway through the movie, I looked her way. I saw her hesitate before looking at me again. I slipped my arm around her as we looked at each other. My other hand went to her chin and I could see the mixture of nervousness and excitement in her eyes. I tilted my head slightly and closed my eyes. I was just able to see her follow suit before I leaned in and kissed her.

It was obvious she had no idea what she was doing. Her lips were closed and pursed. I opened my mouth and my tongue hit the barrier of her lips. But she took the hint and opened her mouth against mine. We made out for quite a while. Her hands roamed my back and my chest while mine stayed to her back and sides. I didn’t want to push things too fast for her.

Eventually she started leaning back on the couch, I followed to keep the kissing going. Soon she was on her back and I was on top of her, but slightly off to the side. I could feel my bulge pressing against her thigh and I was certain she could feel it too. I always wondered what went through her mind as she felt it pressed against her. Was she curious about it, since she had no experience? Was she happy that she was able to get her crush to excited for her? I don’t really know and I never thought to ask.

As we laid there on the couch we co to yes to make out. My hand stayed outside of her shirt but moved to her stomach and worked their way up. She seemed to shift herself and arch her back as if she was greatly anticipating some contact. I slipped my hand up further and cupped her breast. She moaned into my mouth as I took a moment to just feel it. She had average sized tits her for build and I was surprised at how firm they felt in my hand.

She wore a padded bra, which made it nearly impossible to find a nipple to play with and I was going to go up her shirt yet. I promised to take it slow. Eventually we stopped making out. The movie was long over and it was getting late. We cuddled for a bit and made some small talk before she left to go back home, after a proper goodbye kiss.

I replayed that night in my head after she left while I pleasured myself. I’m certain she did the same. I wondered how far this would go in the end.

-NIGHT 2-

The second night started much like the first. It was a week later and I let Mary into my apartment. She seemed a lot more at ease this time, which was good. We made normal small talk and watched some TV. The TV hadn’t been on very long before we were making out again. This time she seemed to know what to do right from the start. Her hands were all over me and mine were all over her. But she kept her touching above the belt. She was a bit hesitant to move further down.

I took the lead and pressed forward. I ran my hand slowly up her side as our kiss continued. My fingers reached the side of her breast and I felt a soft moan echo through my mouth. I think it was more about the anticipation of being touched for the first time. I let my fingers trace the band of her brain under her tits before moving my hand up and cupping one of them in my hand. She squirmed a little and moaned again. Her bra was thick and padded, so I couldn’t do much more than massage it. She seemed to be enjoying the contact. I slipped my other hand under her shirt and let it rest on her stomach.

I could feel her excitement about being touched like this and I knew she wanted more. After some time I worked the hand under her shirt up higher and higher. I could feel the fabric of her bra and moved my other hand away.

I moved my other hand up her shirt as well. They moved towards her back and she lifted herself up just enough for me to get her bra unhooked. I tucked my hands under the band and circled back to the front. As my palms made contact with her tits she arched her back and moaned again. I took a moment to just feel how firm they were. They felt amazing in my hands and I just wanted to keep holding them. But I wanted her to enjoy this as much as I was. My fingers found her hard nipples and I brushed my finger tips over them, I felt her body tremble each time I passed over.

Then I pinched her nipples between my finger and thumb. Her eyes shot open and another moan was pushed into my mouth. I could feel her heart racing and her breathing quicken. My hands were the first ones to touch her nipples, the first ones to feel her breasts. This was all new territory for her.

I finally pulled back and broke the kiss. She looked at me as if she was pleading for more. I smiled at her as I saw the glassy expression in her eyes and her mouth slightly agape, missing my lips and tongue.

I pulled my hands from her shirt and grabbed the hem. I glanced at her eyes again and she nodded slightly. With her approval I pulled her shirt up. She say up enough that I could easily take it off, grabbing her bra on my way by. Her shirt was off, and I dropped it to the floor beside us. I stopped for a moment to look her over. She seemed nervous under my gaze, hoping for my approval. I smiled and kissed her again.

My lips seemed to relax her, but I didn’t keep mine on hers for long. I pulled away and kissed her chin, then her neck, then between her collar bones. She gasped a little as my light kisses moved lower. Her bad was on my arm and squeeze tight as my mouth hovered over her nipple. My warm breath washing over it. I lowered my mouth and pressed my lips to her breast. She gasped again as I closed my lips around her nipple. My other hand moved up to play with the other.

I was practically on top of her. My bulge pressed firmly against her leg. I could hear her heavy breathing as she became more and more excited.

But we agreed to go slow. After giving both of her tits some attention with my mouth I moved back up and kissed her again. I took her hand with mine and slowly moved it towards me. She didn’t put up any resistance. I pulled my lips from hers again and she glanced down at our hands. I rested hers on the bulge in my jeans and removed my hand.

At first she just rested it there, unsure of what to do. But her curiosity got the best of her and her fingertips moved along the side of my shaft. She just rubbed my bulge with her palm and traced the outline with her fingers. Just enough to get comfortable with the idea of touching a cock, even if it was through clothing.

We made out a bit more before she put her top back on and left. The moment she was out the door I had to get myself off. I always wondered if she did the same when she got home.

Source: reddit.com/r/gonewildstories/comments/q7b1bc/mf_giving_my_friend_her_firsts_part_1