How I lost my virginity with Mary [MF]

Kinda long. All participants 18+. Names changed to protect the guilty. This happened sometime in the 90s.

I didn’t lose my virginity until I was 18 and in college. I had a few girlfriends and I wanted to have sex, but I was scared to ask them because at the time I thought women didn’t want to have sex. I’ve never been good at reading signals from women (or men), and I’ve always been really satisfied pleasing myself, so I guess I just never pushed it. Once I realized how wrong I was, I began to understand why women didn’t stay with me as long as I wanted to stay with them.

I met Mary during my freshman year. She was musician student and a volleyball player, and super cute and flirtatious. We would joke with each other and sometimes hang out in when we were in a larger group, but we weren’t that close. I knew that she wasn’t a virgin because my buddy (and roommate) Alex had hooked up with her once after a party, but they weren’t dating.

One day in the spring she came around to our dorm to see what we were up to. It was Friday afternoon, and I was sitting at my desk with the door and windows open. It was a nice day, and I was just about to go outside to join a group playing soccer or frisbee. Mary had shoulder length strawberry blonde hair that she wore in two french braided ponytails that day. Her skin was milky white with the reddish tinge of soft freckles. I remember she had on a mint green tank top and I could see the soft points of her nipples on her big chest. The top came to her mid stomach, right above her belly button. Her tummy was flat and I could see the outlines of her abs. There was a magical ray of sunlight playing through the reddish blonde hairs around her waistline. She looked shiny and sparkly and alluring. Her white flowing skirt came to just below her knees, and although It was slightly translucent I couldn’t tell from the angle if she was wearing any panties. Her long smooth legs went down for what seemed like ages to the cutest little feet clad in simple black flip flops, and her toenails were painted mint green to match her top.

I must have been staring for a bit too long. “Like what you see?” Mary asked. I flushed and looked away. “Matt, I really don’t mind you checking me out. Is Alex around?”

“No, I think he went on a road trip this weekend with Jana and her boyfriend. I’m sorry I was staring.”

Mary ignored my lame apology, but chuckled and plopped down on the bed across from my desk. I resisted the urge to sneak a peek up her skirt, but it took all my willpower. “Huh?” I asked. Mary had said something, but I hadn’t heard it.

“I was asking you if you wanted to come outside with me, dork! Gosh you’re distracted today.” She giggled. I flushed again, but nodded yes. Mary grabbed my hand and led me out into the sunshine. I was wearing basketball shorts and I already had half a boner, so I quickly tucked it in the waistband with my free hand while she led me outside. Holy shit, we were holding hands. What was that about!? My mind was racing, but I tried to stay calm. Mary looked at me and smiled. “You seem nervous,” She said.

“We’re holding hands. This is new,” I said.

“We can stop, if you want.” she continued, but she gripped my hand ever so slightly harder, as if she was hoping that I wouldn’t want to stop. I didn’t want to stop, and I told her so. My heart was pounding. Mary knew what she wanted. I didn’t know what that was but it seemed to have something to do with me and I really wanted to find out.

We walked hand in hand for a few minutes and wound our way to a trail near school that led into the forest where kids would go to get high. Mary knew a lot of people, and they kept saying hi to her, but she would just wave and keep going, tugging me along. I liked that.

Once we made it a ways into the forest, the trail narrowed and we couldn’t easily hold hands anymore. Mary pulled me behind a large tree to the side and let go of my hand. She turned around, looked at me with slight concentration, and then kissed me softly on the lips. She placed her hands on my hips as she did this, and then raised one hand up to caress my cheek and ear and hair. My hands hung dumbly by my sides. She slowly pulled away, but with a slight frown. I had felt sparks, hadn’t she? “Wow, I felt a electricity there,” she said, “that was super hot for me and I have butterflies in my stomach. Did you like it?” She seemed uncertain that I did.

“Mary, that was fantastic.” I said. She grabbed my limp arms by the wrists and flopped them around.

“You have a funny way of showing it, Matt.” And she started to turn away.

I swear a light bulb dinged somewhere above me; I heard it burst and I felt the glass rain down on my head and wash me with understanding – I wasn’t imagining this, Mary actually wanted me to kiss her! I reached out to grab Mary firmly by the hips and pull her to me. “May I kiss you back?” I asked. I didn’t wait for a reply – I just went for it.

She tasted so good. Not freshly brushed, but clean and slightly sweet, but with no specific flavor. She slipped her tongue into my mouth, and I met it with mine. We danced with our tongues for what seemed like ages as our breathing became heavier and heavier. I migrated one of my hands from up from her hip and gently caressed the nape of her neck, her ear and the wisps of reddish blond hair that hadn’t made it into her braids.

Mary moaned in my mouth, and briefly pulled away. “You are teasing me so bad right now, Matt.” “What do you mean?” I asked? “Kissing you is awesome! This is the best day ever!”

Something like an idea or realization suddenly dawned on her face. “You haven’t been with very many girls, have you?”

“A few, I guess. I’ve been told I’m a good kisser.”

“You’re a fantastic kisser Matt, but do you have any other tricks?” I felt a bit bewildered and confused. It seemed like we were having fun, but that I was missing something. Mary smiled at me and then just laid it out there for me. “Matt, I’m really into you. I want you to be really into me. Can you do that?”

I was so dumb. The feeling of understanding I had felt earlier had evaporated. “Like, do you mean sex?” I asked tentatively. “I’ve never had sex before, Mary, I’m not really sure what to do.”

Mary let out a sigh of relief, and gave the cutest little giggle. “I am so glad that you said that. I thought you might not be feeling as into this as I am. I thought maybe you didn’t want to be with me because I had hooked up with Alex, or something.” The thought hadn’t occurred to me, but even after she said it, I didn’t really care. Alex and I were good buds, and we shared a lot. I didn’t think he’d mind.

Mary grabbed the back of my neck with one hand and pulled me into another passionate kiss. I kissed her back, matching her passion. She grabbed my hand that was still on her waist and put it on her stomach, right under her tank top. “You can explore me anywhere you want, Matt, don’t be shy. I want you to.” she whispered in my ear. I slowly rubbed her stomach and began tracing the bottom hem of her tank top. Mary pushed her hips into me and began grinding my erection with her pelvis. She reached behind me and slipped one hand down my gym shorts and firmly grasped and massaged my ass for a bit, and then she began tracing her nails around my ass crack. It felt so good. I moved my hand that was behind her neck down to her lower back and boldly slipped it into her flowing skirt. I felt Mary’s firm bare ass, and I moaned. Her ass was strong and athletic and I could feel her power in my hand. Mary groaned too. I explored her bare ass and I realized that she wasn’t wearing any panties. That revelation nearly sent me over the edge. It was so sexy. Since I liked how it was feeling with her caressing my ass crack, I returned the favor. She smiled through the kiss, pulled away briefly and said “Now you’re getting the hang of this.” Emboldened, I slid my other hand under her tank top, and began to fondle her breast, and circle her nipple with my finger. Her breasts were big, though, and it was a tight fit.

Mary pulled away, grabbed my hands and, whisper-growled “Matt, let’s find someplace more comfortable and farther off the trail.” She stroked my erect cock through the front of my gym shorts and then grabbed my hand to pull me deeper into the woods off the trail. We didn’t have a blanket or anything, but the forest floor was soft with leaf litter, and I wanted to stop there so we could get back to business, but she pulled me onward, and soon we were in a small secluded clearing with a grassy meadow and a nice big tree stump in the middle of it. I’m not sure what kind of tree it was from, but the stump was wide and smooth, about the height of a low coffee table. It was enough for two people to lie on and looked pretty clean. It was perfect.

Mary spun around to face me with a huge smile on her face. “Matt, this clearing is so pretty.” I grabbed the hem of her tank top, and she nodded and raised her hands. I pulled it up fast, but it got kinda stuck on her large breasts and they dropped out and jiggled sexily as I threw her shirt aside. Mary yanked off my t-shirt and pulled down my gym shorts and boxers to reveal my erect cock which bobbed around for a bit. The tip was glistening at the end with a strand of precum that dangled about 4 inches off the head and bobbed along with my dick. Mary quickly squatted down, caught the precum strand in her mouth, and licked the rest of it from the head of my cock. She stopped short of sucking me though, and just looked up at me her deep blue-green eyes for a minute. My cock was framed by her two large breasts and lined up perfectly with her slightly open mouth. She stuck out her tongue and swirled it around my cock head. I moaned in ecstasy. Mary moaned too which sent a vibrating hum down my shaft. I groaned and I tried my best not to ejacuate right then. Mary let go of my cock with her mouth, grabbed my balls with her hand and gave them a squeeze, and tugged them down. “Please don’t cum, yet” she said. I held on for dear life, and somehow the orgasm edged, my dick drooled out a huge plop of precum, but I didn’t cum.

“Phew,” I said, “that was close.” She nodded.

Mary was still wearing her skirt, and since the rest of our bodies were naked, that just seemed out of place to me. The hem was just falling over her knees as she was squatting down, which was blocking any chance I had to look up (down?) her skirt. I lifted my foot just a bit and flipped the hem towards her which exposed her pussy to me. It glistened wetly, and a large drip was forming by her taint. I could see a wet spot on the back of her skirt. She was unshaven, and her neatly trimmed pubic hair was strawberry blonde too and slick with her juices.

I wanted to smell her and taste her and to bury my face into her pussy and just enjoy being with her in this wonderful place. Mary stood up, pulled her skirt over her head, and threw it aside. She then pushed her body into mine and wrapped a hand around my cock. Her breasts pushing into my chest. I arched back a bit, and took one breast in my hand and brought the nipple to my mouth, sucking and licking it. I snaked my other hand down her flat tummy, through her short bush and stroked my fingers around her pussy. I had no idea what I was doing, but she moaned and bucked against my hand. “Since this is your first time, you might cum right away” she whispered. “Don’t worry, I want you to cum inside me.”

With that, she lowered us both to the stump and she laid down on her back. She grabbed my cock and pulled me into position over her, with my hands by her head. She guided me to her wet and ready opening and as I thrusted at her hand she moved it out of the way my cock entered her velvety pussy. She was wet enough, but she was tight. I fit snugly and had to push hard to get in all the way. I grunted, and she grunted as I buried my cock to the hilt. And, feeling that I was about to orgasm if I moved another muscle, I stayed buried for a minute and kissed her deeply. Then with one hand, I pinched her nipple, and rolled it in my fingers.

Mary didn’t want to pause for long, and after a moment she began to buck her hips against mine, rubbing the top of her pussy into my pelvis above my cock. I matched her thrusts for a few moments, but it was too much. “Mary, I’m going to cum right now!” I grunted urgently.

“Uuuunnnnggghhhhh!, I’m coming, don’t you dare stop!” She yelled, and I could feel her pussy contracting around my cock. I came so hard and for what felt like so long. And Mary also kept cumming and moaning and telling me not to stop. I fell into her, and we kissed and laid like that for a while; our sweaty bodies rising and falling as our breathing calmed. My erection began to soften and I pulled out. I looked down and my cock was covered in cum and Mary’s pubic hair was a white, sticky mess. We both chuckled. When I rolled off, Mary put her head on my stomach and gently sucked me clean.

“Mary, that was amazing. Can we do it again?” I asked.

“That was pretty good for your first time. Matt. I can’t wait to do it again now that you’re more experienced.

She sucked me back to hardness and tried to guide me back into her, but before she could, I knelt between her legs and licked her pussy. I gently licked from the bottom to the top, and she inhaled sharply when I reached her clit. I didn’t know my way around a pussy yet, but Mary gave me a quick anatomy lesson and told me what she liked. As I flicked my tongue around on her clit, I put two fingers in her pussy and massaged the top wall of her love tunnel, thrusting in and out. She moaned and begged for me to fuck her again, but I kept going with my tongue and fingers and pretty soon she screamed out in ecstasy that she was coming again. A few startled birds flew out of the trees and away from the clearing. Her hips bucked and bucked, and her pussy clenched at my fingers until she begged me to stop because of the sensitivity. Then she hopped up, pushed me back down to the stump and straddled me, quickly impaling herself on my throbbing, rock hard cock. She looked me in the eyes, and growled. “Fill me up again, Matt, I need your cum.”

I was so turned on that even though I lasted a little longer this time, I still came pretty quickly. She lowered her chest to my face and I took turns sucking her right and then her left nipples as I thrusted into her pussy. And pretty soon I couldn’t hold back anymore, “I’m coming again, Mary, Jesus fuck you are so fucking sexy and I am so turned on!” After I filled her for the second time, she hopped off and semen pooled around my cock. Mary cleaned that too and then joined me for a snuggle on the log. We languidly kissed and fondled for a long time after that, telling one another how good it had been. I got hard again, but the afternoon had turned to evening and it was starting to cool off, so we decided to get dressed and go back to the dorms.

We parted ways at my room with a passionate kiss, and I fell asleep dreaming of Mary and her tight body.

Please let me know what you think. Comments and PMs welcome.

Source: reddit.com/r/gonewildstories/comments/bhqj04/how_i_lost_my_virginity_with_mary_mf