Since a lot of folks seemed to like my last story (which you can find here: https://www.reddit.com/r/gonewildstories/comments/n1hlti/a_final_goodbye_before_moving_fm_long/?utm_source=share&utm_medium=ios_app&utm_name=iossmf ), I decided to try my hand at writing up another time between myself and Tristan. I’ve enjoyed writing these, so if they speak to you please let me know in the comments! As before, skip to ** for the saucy bits :)
I [F24] didn’t initially plan on losing my virginity that night. But it was a long time overdue and at a certain point I was ready to just be done with the burden of when my first time would be. I had been ready to have sex for quite awhile at that point (and had basically done everything up to that point so I wasn’t entirely inexperienced), but I had built it up in my mind: I wanted it to be with someone I cared about and trusted, I didn’t want it to be a one time thing, and I wanted it to be somewhat special. Ideally I wanted to be in a relationship first. But I never seemed to have much luck with those. This was a few years back and at the time I was 24. (About me: dark long curly hair, big brown eyes, petite, average weight with large DD breasts). There were moments over the years in my late teens/early twenties that I could’ve easily made the choice to sleep with someone, but all of those situations didn’t feel right. A lot of it had to do with finding guys that just wanted to fool around without committing. And for me, even if I wasn’t in a relationship, I didn’t feel comfortable taking that step unless I really knew someone and trusted them (I’m still this way).
My “relationship” with Tristan [M35] was not a straightforward one, but it was one built on friendship, support, and exploration. He was poly at the time, and though that’s something I supported for him, it was something that I knew would never match up with my desire for a monogamous relationship and so the reason neither of us made our relationship official. We tried to not date at all…but that never seemed to last very long. We had a surprising and fun connection, and it felt better to use this opportunity to explore my sexuality with some I trusted, rather than not see him at all, especially when dating as a 24 year old virgin in a major city was so difficult.
It was incredibly frustrating because I could tell that I loved sex. I loved all the other aspects of hooking up and I wanted to be able to sleep with the guys I went out with, but I couldn’t change what I felt in my heart was really important to me about my first time. I needed my introduction to penetrative sex to be positive and in a safe environment.
Cue Tristan [M35]. To give you an idea of what he’s like: dark hair, around 6’, and slender but muscular. He’s also very outgoing and playful. We met in the performing arts community and both worked various artistic jobs (a lot of times collaborating on projects together and performing together). He occasionally worked at a music venue in my neighborhood, and so on those nights there would typically be an open invitation for him to come over after work if he wasn’t too tired. Since this would usually be 1 or 2am, sometimes it would just involve us “hanging out” briefly before he headed home, or cuddling and falling asleep together, while other times things become more erotic. This, dear reader, was one of those times.
And as a reward for getting through all the scene setting above, here’s the saucy bits….
**
I had dressed in a comfortable summer nightdress just in case he came over. Easy access underneath, and easy access on top too. I lay in bed waiting to hear from him. I liked the anticipation. Knowing that I was waiting for him and that anything could happen. On top of everything though, I just enjoyed seeing him. He had a way of making me feel sexy and desired.
Just as I was about to doze off, I got a text from him. He was leaving and on his way over. My heart fluttered in giddy anticipation and I was immediately awake again. Not only that, but my body was incredibly awake too. I knew I needed him in some way tonight. Whether it was just cumming from his fingers or oral, my “sex” drive was turned on that night and I was anticipating another night of hooking up within our pre-established boundaries.
We had many discussions over the year and a half we had been on/off seeing each other about boundaries and what we were looking for from each other. Since he would see other people, he was upfront that he was able to get sex from those experiences, so he was perfectly fine exploring things with me without going all the way. Though we both voiced our desire to want to sleep together, he made clear that it was basically up to me to make the decision for when I was ready. In the meantime we had a lot of fun playing within those boundaries.
Tonight was no different at first. He texted that he arrived and so I tiptoed down to the lobby to let him in. My buzzer was broken and so it necessitated going downstairs in my skimpy clothes to greet him, hoping I wouldn’t run into any of my neighbors. I opened the door and he was already grinning to see me. I kissed him joyfully and led him inside. I took his hand and led him up the stairs, walking just in front of him. Halfway up the first flight though he stopped me and stood right behind me on the steps. He caressed his hands over my hips and ass, eventually sliding his arms around me and holding me to him. I lent into him with my ass, feeling him behind me. I could tell we were on the same page tonight. Then I broke free and laughed, pulling him the rest of the way up the stairs.
Once we got in my apartment we went right to my room. I turned around and wrapped my arms around his shoulders, rising up on my tip toes to kiss him deeply. He leaned into the kiss and we both smiled, still with our lips locked. He was an amazing kisser. I could, and did, kiss him for hours on end and not get tired of it. In fact, the first time we crossed over from friends to something romantic, involved us going out for a drink one night and then us very innocently making out for hours in the bar and in his car.
I walked over and sat on the edge of the bed and waited for him to take his shoes and jacket off, opening my legs slightly. When he finished, he slowly walked up in between my legs and ran his fingers through my hair and over my shoulders. I slowly undid his belt and slid the belt out out, letting it fall to the floor. Then I proceeded to unzip his fly as I looked up at him with my innocent eyes, biting my bottom lip.
This was part of our dynamic that played into how sexy it was hooking up with him. I felt free to fully amplify my innocence, knowing he would respect my boundaries, and he could play up his subtle dominant teacher persona. Our age difference was a little over 10 years too, so we always found it incredibly hot leaning into that too (what can I say, I like an older guy!).
As I pulled down his pants he leaned down and kissed me, weaving his fingers in my hair and grasping some of it in his fist. I blindly rubbed at his bulge until I felt it start to awaken. We broke the kiss and both got situated on the bed, him shedding his shirt and pants as I laid back. He laid next to me and leaned over me to continue our tongue tango. I ran my hands up his shoulders and back behind his head, crossing my arms and pulling him in close.
He moved to my neck…oh dear god my neck. I don’t know what it is about a guy kissing, breathing, and nibbling on my neck, but it’s one of the things that makes me immediately weak. And contrary to some people’s preference, I love hickies! He kissed and sucked up and down my neck. I squirmed underneath him and kept running my hands over his body. One of his hands found it’s way to my breasts and pulled down the thin material separating me from his hands. He kneaded my breast and ran his thumb over my sensitive nipple. I grabbed his face and pulled him into a deep kiss as he worked my nipple with his fingers. He then brought his mouth down to my other breast, lowering the material on that side too so I was fully exposed to him.
It’s so incredibly sexy when a guy focuses on your pleasure. And Tristan was an expert at that. As he sucked and licked me, he looked up to make eye contact, picking up the urgency as he saw how turned on I was by him. He moved his hand from my breast and he brought it down, gently guiding my legs open. I eagerly opened them and waited for him to touch me. I was on cloud 9 but wanted more. To feel his hands manipulate me and tell me what to feel.
He slowly reached his hand down the front of my panties and when he finally touched my clit I closed my eyes and leaned my head back, moaning to express how good it felt. He knew he had me in the palm of his hand, quite literally. As he kept sucking on my nipple he began to gently rub me. I caressed his face with one free hand as I brought the other up to the now free nipple. I pinched and pulsed my finger over the nipple as I felt the ecstasy build up from all the stimulation.
My breathing became more erratic as Tristan worked me up to my orgasm. My moans of pleasure growing louder and louder, I could feel his satisfaction at what a good girl I was for him. He lifted his face from my breast and kissed me urgently, ramping up his attack on my clit. His mouth briefly broke away from mine as he watched me inch closer towards release. His eyes were fierce and demanding me to give into him. I was so close. “Oooh baby yes, oooh oooh” I whined as I felt my orgasm build. He was panting himself as he watched me squirm under his strong arm. “Good girl” he encouraged me. I quickly hit the peak and came, grabbing onto his arm, and immediately pulling his hand away due to my sudden over sensitivity. He watched as I rode it out, trying to catch my breath.
As things started to subside I looked over at him and gently laughed, the euphoria of what I was feeling coming through in a way that brought us back to reality, dropping our hyper sexual selves for a moment.
“Oh god, you turn me on so much, you know that?” I told him. He smiled and playfully said “I like turning you on”. “Well, you’re really good at it”.
We cuddled together for a while until he asked if he should go home at that point or spend the night. I hugged him close to me and playfully whined “Noo I don’t want you to go!”. “Are you sure? It’s late and maybe I should let you get to bed now. I’ve already woken you up and distracted you enough”. “No.” I said, as defiantly as a little girl putting her foot down. “You’re staying over, I like your distractions”. “Oh really?” he said and smiled as he slid his hand back down to my pussy…
Source: reddit.com/r/gonewildstories/comments/nj02ti/my_longawaited_first_time_fm_long_part_1