[FM] How I Met The TA Who Took My Virginity

Disclaimer: the name I use for myself here is not my real name.

As many of my followers have probably read, while sexually active early in life, I was raised in a deeply oppressive, sexually conservative Christian community, and didn’t have intercourse until I left the area my first year in college.

At this point in my life, I was really beginning to struggle with the oppressive norms of my community and how they conflicted with my sexual activity, fetishes, and attraction to all genders. I was also starting to work through the guilt of being labeled a slut at an early age by abusers and how I incorporated that label into my daily behavior. To help me better understand my own past, I decided one of the first classes

I would take would be able gender and sexuality.

The first day of class was so eye opening! Not just reviewing the syllabus and curriculum, but being surrounded by like-minded people. For the first time, I wasn’t in the minority. Sure, there was a bit of discomfort the first day, but after the instructor led us through some ice breakers, everyone talked openly and philosophically. There was no shame in sex. No shame in kink. No shame in powerful women who thought for themselves and didn’t live to please a man. No shame for being bisexual or pansexual. It was incredible!

After our instructor did introductions and ice breakers, she handed the class over to her TA named Dylan. Dylan was a grad student in his early 30’s who was doing an interdisciplinary degree in sexuality, gender studies, and philosophy. He was 6’1”, athletic, and Pakistani-American. He had a slight accent from being around his family, but was raised entirely in the US. He was wearing a cobalt blue knit long sleeved shirt with the sleeves pushed up to his elbows, khaki pants, and had a sexy pair of glasses. He also had beautiful brown almond-shaped eyes, scruffy hair that was always a bit wild but always looked great, and was absolutely dreamy. Besides all his attractive physical features, he was incredibly smart and well spoken.

He began by asking the class delving questions about our various experiences and backgrounds, and I figured it was now or never, so I told everyone about my conservative upbringing. Dylan was fascinated, and also a little concerned. After we started working on an in-class free write assignment, he casually walked over to me, kneeled down, and asked me if I was okay. He said that he could understand a bit where I was coming from, being Pakistani, and said he was always around if I needed someone to talk to as I adjusted to my new environment. It was extremely kind of him, and without knowing it, he had said exactly what I needed to hear. I didn’t know how to broach the subject of my past and my sexuality with my roommate yet, and was extremely nervous about it. I thanked him and went back to the assignment.

After class, I hung back, clutching my books to my chest, waiting for the rest of the class to ask their questions and head out. After everyone was gone, Dylan looked up from his desk and saw me. I walked over to him and told him I would be very grateful for some guidance and asked if he had office hours. He did, and they happened to be right now after our class. He invited me back to his office, which was down the hall, and I said great!

Dylan’s office was like planned chaos. There were stacks of books and printouts in piles everywhere, and the shelves that lined the walls were filled with books on philosophy, sexuality, gender, social justice, and psychology. I looked around in awe.

“Are all of these yours?” I asked.

He smiled and said, “yes, of course.”

“Have you read them all?” I inquired

“Most of them” he responded

Then he gestured to a chair in the corner and invited me to sit. I did and then he sat down, crossed his legs, clasped his hands together, leaned back, and invited me to tell my story. I don’t know exactly what it was about him. Maybe knowing he also came from a culture of sexual oppression and norms, or maybe because he studied this for his job, or maybe some part of me knew he was the exact right person for me at this point in my life, but I ended up telling him almost everything. I started with my upbringing and a general description of my religion: the oppression, the customs, the misogyny. Then I talked about how the culture deeply conflicted with my feelings, but that I had been having trouble parsing out what was me and what was my upbringing. We talked for about two hours before he looked down at his watch. I suddenly realized how much time had passed, and got very self-conscious.

“Oh! I’m sorry. I’ve been rambling on for so long. Am I keeping you?”

“Not at all” he said, “I just have to head out. Maintenance said they would be coming by to put in a new shelf in a few minutes and I told them I’d be out of the space, but I’d like to keep chatting. Would you want to come with me to the campus café?”

“Sure! Come to think of it, tea sounds really good right about now.”

So we headed out. He bought me a tea and scone at the café and we found a couple of comfy chairs in a sunny nook upstairs and I continued telling him about my life. This time I started to get more personal, shyly telling him about my family. He leaned in, set his chin on his fists, and listened attentively. He sympathized with me over the authoritarian dynamics of my family. He, too, had a demanding father.

After tea, we walked together through campus, me holding my books to my chest and him strolling next to me with his hands in his pockets. We reached a park bench and, while still letting me talk, he gestured an invitation for me to sit. I did, and he sat down next to me. It was then I started to tentatively tell him about the abuse, starting with my father’s corporal punishments. It was the first time I had told anyone, and I started to cry. He leaned in, took my hand and held it gently. “I’m so very sorry” he said. “That never should have happened to you.” He shared with me that his father was also abusive, and it took him a long time to come to terms with his past. He did the best thing someone could do. He sat there and witnessed my pain. I cried. He held my hands. And when I was all cried out, he asked if he could hug me.

I nodded. He embraced me, kissed the top of my head, and told me he was always here to talk. Then he gave me his cell number and said I could text him anytime. He said he had to run to a dinner meeting, and asked if I would like to meet again for tea next week. I nodded, gratefully.

We met for tea at least once a week for a couple of months. I learned all about his family, his education, and acceptance. I told him everything, even about my experiences with Carlos, and how it shaped my sexuality with other partners. He always listened deeply, without judgement, and was extremely respectful. He was my very first real friend who knew everything about me, and I was so grateful.

After telling him the secrets of my past, we moved on to other topics. TV, film, literature, music. He introduced me to a wealth of authors, on the subjects of gender, sexuality, religion, and science and poetry (Thoreau being one of my favorites). I introduced him to Lady Gaga and Taylor Swift (which took some convincing. Lol). He always challenged me, never judged me, and encouraged me to grow and learn. It wasn’t long before I started to fall in love with him.

My birthday was fast approaching. I was still struggling to make friends, and hadn’t gone to any parties (alcohol was still something I wasn’t quite ready to try. I hadn’t had any since after Carlos moved away), so Dylan suggested he take me out to dinner at a nice local restaurant. I was over the moon! The night of our dinner, I picked out my prettiest dress. It was made out of long, flowy, gauzy material that looked like soft crepe paper and was white with small blue, orange, and yellow flowers spiraling down it. It was a b-neck cut and had small buttons down the front, and had a cinched empire waist. I braided the front of my hair across the top of my head into a crown, and finished off the look with gold strappy sandals. My roommate, Jackie, smiled at me and said, “hot date?” with a wink. I blushed.

As someone who was so seductive in my hometown, at college, I was totally out of my element. Even though I was more accepted, I didn’t know how to function anymore, and I had become exceedingly shy. Jackie was very nice but we hadn’t clicked yet. She was a high achieving science student who was almost always in class, labs, or at her study group, so we didn’t hang out much.

I told her, no, it wasn’t a date. Just a dinner with a friend for my birthday. She slammed her book closed and said, “your birthday?! Why didn’t you tell me?! We HAVE to celebrate! What are you doing this weekend?”

I was surprisingly happy to hear her say this. I hadn’t realize how much I needed community, and I thanked Jackie and said I would love it. She told me she would do all the planning. All I had to do was send her a guest list and show up. I was tearing up, and went over and hugged her. Then grabbed my purse and went to meet Dylan.

Dylan was already at the restaurant when I arrived. It was an Italian place off campus. The kind with cloth napkins and table clothes. I walked in and scanned the room to see him waving me over to a table in the corner by a window facing the restaurant’s garden out back. He was wearing a blue suit, no tie, with the jacket unbuttoned. He had combed his hair, which sat in beautiful waves on his head. He looked good enough to eat.

I walked over and he got up, gave me a quick hug, and pulled out my chair. I sat and he poured me a glass of water. On the table was a gift bag, shining gold with tissue paper in it. He pushed it towards me and said with a big smile, “I’m not good at waiting, open it now.” I gingerly reached in the bag and pulled out a beautiful leather bound diary with a mandala on the front. The leather was deeply blue-green, almost iridescent. It was the most beautiful book.

“It’s a place for you to write your story. You can write down your personal discoveries and record your journey. But there’s more” he grinned.

I reached back in and pulled out a green velvet covered box. Inside was a gold bracelet with a lotus flower design in the middle. On the inside was an engraving, “All good things are wild and free”. A Thoreau quote. I gasped. Tears sprung to my eyes. These were the most thoughtful gifts I had ever received from anyone. I put the bracelet on and extended my arm to admire it on my wrist. “It’s perfect,” I told him. Then I got up, walked over to him and kissed him on the cheek. He got a bit embarrassed and quickly said, “Oh, it’s nothing much. Everyone should have a journal.”

The rest of dinner went swimmingly. Dylan had a glass of red wine and the chicken piccata and I had water and the veggie lasagna special. At the end of the main course, a waiter came over with a small candle lit cake and placed it in front of me. It was decadent chocolate with blackberry drizzle. We shared it and raves about the food. At the end of the meal, he asked me if I would like a ride home, and I nodded. He said he was parked down the road near the park. It was a warm night for November, but still have a bit of a bite in the air, so he took off his jacket and put it around my shoulders and walked along with his hands in his pockets, like always.

As we walked, I started to feel more like myself than I had since getting on campus. We made small talk and laughed at these horrible jokes our waiter told us during dinner, and how he had been smitten with me, so much so that he spilled the water twice and stammered every time he talked to me. Dylan, hands still deep in his pockets, said, “You do look very beautiful in that dress. I bet he wasn’t expecting such a pretty woman to sit in his section.” I blushed, but thankfully it was too dark out for him to see.

When we reached the park by his car, I sat down on a nearby bench and invited him to sit. I told him how much the dinner and gifts had meant. I confided that I hadn’t had much luck making friends yet, and explained how I had oddly become rather shy, except with him. He said he thought he understood, and had gone through something similar himself when he left home the first time. He said it felt like he had temporarily lost his footing. That was it exactly! It must have been a combination of my giddiness at the evening and the feeling of being so comfortable and understood, but before I even realized what I was doing, I leaned over and kissed him. It was gentle and sensual, and lasted only a moment before he gently pushed me away.

“Woah, woah, woah,” he said, “I’m your teacher, not to mention a great deal older than you.”

My hands went to my lips in disbelief. I was a sexual person and I loved seducing men, but what was I thinking? This wasn’t a fuck buddy or some guy I wanted to manipulate. Dylan had become my closest friend, and I didn’t want to do anything to jeopardize that. Not to mention get him fired. My eyes went huge when I realized what I had done. I looked him straight in the eyes and said, “I’m so terribly sorry.” Then I got up and ran home.

I knew I would have to see him again the next day in class, and was mortified. I couldn’t bring myself to go and called in sick. When I didn’t show up, he texted me to ask if I was okay. I told him yes, I had just come down with a cold and he said he hoped I felt better soon.

I had his class every other day, and I couldn’t miss another without impacting my grade, so when Friday rolled around, I reluctantly went. We acted like normal, but clearly there was a distance between us. After class, I left before he was done talking to other the students.

The following night was the party Jackie arranged for me, though I didn’t feel much like celebrating anymore, but she had shown so much care and had invited some of my classmates and her friends, and I couldn’t disappoint her, so I put on a cocktail dress I had bought earlier in the year and my game face. The cocktail dress was red, clingy, and short, much shorter than anything I was allowed to wear at home.

The party was in our common area, and when I walked in at 10pm, she had the whole thing decorated with streamers and balloons and a big sign on the wall that said “Happy Birthday.” There was a big folding table piled with chips, dip, cookies, a cake, some gifts, and a punch bowl filled with some kind of purple drink. The music was on, the lights were dim, and people were chatting in small groups. I scanned the room to see if Dylan was there. I had put him on the guest list, but didn’t expect him to come even before my stupid move. I didn’t see him anywhere.

When Jackie saw me, she yelled, “She’s here everyone!” And immediately everyone started to sing Happy Birthday. It was so thoughtful. Afterward, Jackie handed me a drink in a big red cup and introduced me to her friends. They were all really nice and we got along great. Jackie whispered in my ear that there was vodka and triple sec in the punch. I hadn’t had alcohol since I was a kid, but I was feeling so down and Jackie worked so hard on the party that I figured this was as good a time as any to try it. The punch was tasty. Very sweet, but there was definitely a bite to it from the booze. I downed the cup and got another. After the second cup I started to loose up and feel pretty good! Conversation was going well with my new friends, and I had a nice buzz. Then Jackie pulled out twister and we all played. It was a brilliant idea. We were all a bit tipsy from the booze, and trying to maneuver our bodies for the game was great fun. We all laughed hysterically, and I almost forgot how sad I was.

After a couple rounds of twister, Jackie rolled up the mat, dimmed the lights, and turned up the dance music. Then she grabbed my hand and pulled me into the middle of the room and started to dance with me. It was a lot of fun, and soon everyone was dancing. I was on my fourth or fifth cup of punch and feeling quite sexy in my cocktail dress, so I went up to a guy named Mitch, one of the guys on Jackie’s friend group, and asked if he’d like to dance. He said sure and I grabbed his hand and pulled him into the center of the room. I let my body take over and started to dance seductively with him, bending over in front of him and popping back up. Grinding against me. Throwing my hair back and forth. It was nice to feel free again.

I danced like that with Jackie and her friends for a couple hours and was glistening with sweat when I looked across the room and saw Dylan standing in a corner on the periphery of the party looking down with his hands in his pockets. I was pretty tipsy but not drunk and feeling confident after an evening of fun and decided to walk over and apologize.

Dylan looked up and saw me and gave me a sad but warm smile. I asked if we could go somewhere quiet and talk, and jokingly said he didn’t need to worry about any unwanted advances. He said he’d like that. Then he bent down and grabbed a bag from behind him. The bag my gifts were in. I had totally forgotten. He said, “you left these behind the other night. I hope you’ll still accept them.” I nodded and he took out the bracelet, gently held my wrist, and put it on. I looked up at him and couldn’t hide the love I felt and thanked him. Then we walked over to the escape stairwell down the hall and closed the door.

I apologized again for my behavior. I told him how much I valued his friendship, and that I didn’t want to do anything to jeopardize that or his career. I understood the risks. He said he valued our friendship, too. I expected him to give me a hug and leave after that, but he didn’t. Hands still in his pockets, he looked down and shuffled his feet a bit. Then he told me I was the most extraordinary woman he’d ever met, and that he wished the circumstances were different. My eyes went wide. Did he love me, too? Or was he just trying not to crush a young girl’s heart? I asked him if he wanted to come back to the party and he agreed. I asked Jackie if we could pull out twister again, and we all played and laughed and fell. Dylan played, too, and when he had to put his hand on the same circle as mine, his fingers caressed mine. I locked eyes with him and electricity shot through me. I hadn’t had a sexual encounter in months, which was a long time for me, so I immediately got turned on. Then I snapped myself out of it. We all had a few more drinks and danced. Dylan was starting to loosen up more and have fun. He hit it off with everyone, telling stories and making people laugh. We both had a couple more cups of punch and things seemed to get easier with us. We were almost back to normal. After dancing some more, I started to get hot and decided to step outside for some fresh air and asked Dylan if he wanted to come with me.

When we got outside, we walked around the side of the dorm so we could talk. I told him how Jackie planned the whole thing and how this felt like a turning point for me socially. He smile a genuine smile and said he could see that. He looked at me strangely for a minute, and then said, “I’ve really missed you this week. I hope I didn’t hurt you.” Maybe it was the booze, or all the pent up feelings I hadn’t processed, but I started to cry. “Shit!” He said, and started to tear up, too. Then he came closer and wrapped me in a warm embrace. He buried his head into my neck and whispered, “I never want to hurt you. You can’t know how much you mean to me.” That was it. That was all my desires could take. I was tipsy and horny beyond anything I’d ever felt, and I was deeply in love with my best friend who was as hurt as me. In that moment, everything else faded away. Our age. Our status. Our dinner. It was just us. He started to let go and our eyes met. He must have felt the same because we both leaned in this time and kissed each other. It was the single most sensual moment of my life up to that moment. His mouth was warm and his lips were soft and experienced. As he kissed me, he threw his arms around me and lifted me off the ground. I tangled my fingers in his thick, wild hair and pulled a bit and he moaned.

“Oh God, Dylan. You taste amazing.”

“Ally, I’m in love with you. I’ve never in my life loved anyone like I love you.”

I died inside. “I love you, too, Dylan.”

And he picked me up and carried me to his car. We sat in his car talking about everything. How our feelings developed, when we each realized, and what we could do about it. It turned out that since he was a student, there was no rule about us dating, but our age difference was a pretty big concern in terms of how others might perceive us, and he did have positional power over me as my TA. We ultimately agreed that we should keep it a secret until the end of the term, and next year we would make sure he didn’t teach any classes I was in and vise versa. We also agreed to be careful with public displays of affection.

After we talked, Dylan had sobered you enough to drive and invited me back to his apartment. I immediately agreed, pulled out my phone, and texted Jackie a huge thank you and told her that I went out with some friends to a bar.

We got to Dylan’s place and he grabbed my hand, walked me to the door as he unlocked it and invited me in. His place smelled like books and incense and curry. It was warm and cozy, a comfortable place. There was a pipe on the coffee table, and an open book next to the couch. Unlike his office, it was extremely tidy. He asked me if I’d like something to drink, and got us both a glass of water.

We sat down on the couch together and I told him I liked his home. I looked at him and sighed. I couldn’t believe my luck. My life. After everything, I had fallen in love with this incredible person, and he loved me back. He knew everything about me and didn’t think I was a slut. He wasn’t ashamed of me. And he didn’t fetishize me, either. In this moment, I decided to embrace my sensuality. I knew he would accept me. I knew my sexual desires wouldn’t surprise him, and I knew they weren’t the reason he loved me, either.

I took a swig of water. Pushed back the coffee table. Stood up, and let the spaghetti straps of my dress slide off my shoulders. I walked in front of him as he started up at me. I planted my high-healed feet wide, cocked my head, bent over at the waist, and gently pushed on his chest so he was forced to slouch back on the couch. Then I kneeled one leg on one side of him and one on the other so I was straddling him. I leaned forward and he leaned up to kiss me, but I pushed him gently back again. I leaned into his neck and huffed warm breath onto his neck and whispered, “You have no idea how long I’ve wanted to do this.” And then I licked his ear and his neck. He moan, “Oh God, Ally” and reached up to embrace me but I grabbed his hands and held them down as I kissed under his chin and down to his collarbone and started to grind my hips against him. He moaned again. I looked back up and kissed him long and deep. He tasted delicious. Salty and sweet.

I still had his hands pushed down, but in a burst of passion he broke away, grabbed me around the waist, and flipped me over so I was laying on the couch and he was on top of me with my legs wrapped around him. He kept kissing me long and deep. Then he whispered in my ear “pick a safe word” and I knew I’d made the right choice. “Thoreau” I said and he looked at me and smiled with such affection, then kissed me long and deep. Then he grunted a deep, primal grunt and pulled my dress up around my hips, ripped my panties down my legs, and buried his face in my pussy. He was an expert, and he was ravenous. He licked me hard and deep, and moved his head quickly from side to side while he stared at me. Then took two fingers and gently entered me. Probing me long and deep, searching for my g-spot. When he found it, he started to massage and bump it with his fingers, slowly at first and then harder all while eating me like there was no tomorrow. He took his face away and said, “you taste divine. Now cum for me.” Then he went crazy. He licked and fingered me with such vigor that I came immediately. “Mmmmmm” he said, as he licked my vagina and then his fingers.

Now it was my turn! I pushed him off me and onto the other side of the couch with a giggle. His dick was hard inside his pants.

“Dylan, I’ve never loved another person before. I didn’t understand how it felt. But I love you. I’d do anything to make you happy and to keep you safe. I’m so grateful for you. I know you know all about my fetishes and kinks, and I can’t wait to explore all my sensuality with you.”

“I love you, too, Ally. We are going to experience so much together, both in the bedroom and out of it. I will go at your pace. As long as I’m with you, that’s all that matters. Come here!” And he pulled me on top of him and kissed me again as we laughed with joy. I sat up on him, pulled my hands through my hair with a stretch towards the sky, and started to grind my hips, smiling down at him. Then I grabbed my dress where it was stuck around my wait and lifted it over my head so I was completely naked on top of him. He grunted that primal grunt again that I would learn was his signature sound when he was exceptionally turned on. Leaned forward, and started to suck on my left breast while massaging my right with his hands.

He looked up then pushed me back at the waist like he was sizing me up and said, “Ally, you’re more beautiful than I could have imagined”

I leaned down and ran my fingers through his thick wavy hair, tugging his head back gently and whispered in his ear, “Take off your shirt, professor” and he laughed and obliged.

His chest was muscular with thick swirls of black hair that trailed down his stomach and into his pants. I put my hands on his pecks and felt his strong body, then kissed down his chest, stopping to lick his nipples (which made him moan loudly! A man after my own heart!), and followed down his slim six-pack until I reached his pant’s waistband. I paused, rubbed my tits against his bulge (another moan), and slowly unzipped his pants. He was wearing tight black boxers and his cock was starting to poke out the opening. I pulled his pants down and licked along the line of his underwear on his groin, then I spread his legs and wiggled down between them and started to lick the inside of his thighs as he started to breathe heavily. Finally, I pulled his boxers down to his knees, revealing his beautiful cock. It was uncut, thick and girthy, and about 7 inches of gorgeous. His balls were large and tight against his body. I took a moment to sit back and admire him.

“You have one of the most beautiful cocks I’ve ever seen,” I told him, and he raised an eyebrow at me and laughed.

I reached down and touched his penis and it jerked up. He leaned back and closed his eyes, gasping. Then I bent over and licked all around it, being careful not to touch his cock with my tongue yet. Finally, I scrunched all the way down and started to lick and suck on his balls and he let out a LOUD moan. I grabbed his shaft and gently started to rub up and down as I sucked on his nuts. Then I slowly took my tongue and glided it up his shaft. I teased the tip, going around in small circles while smiling at him, and then I plunged his cock deep into my throat.

“Shit, Ally! You’re gonna make me cum! Slow down!”

I looked up and him and said, “You won’t cum until I’m ready for you to!” And winked at him. I knew exactly how to edge him into oblivion! As his cock got harder, I eased up and lightened my sucking, alternating between licking him with the tip of my tongue and plunging and sucking his shaft depending on how hard he was and how much he throbbed.

After what felt like worshiping his cock forever, I leaned back and said, “I want you to fuck me tonight”

He was visibly shocked and sat right up. “Ally, no. Tonight? You’re a virgin.”

“I know what I want, Dylan. I want you inside of me, as soon as possible. I can’t sit here sucking you without my body aching for you to fill me up.”

“Ally, do you know what it’s like to lose your virginity?” he asked, “It can be painful. And are you on birth control?”

“I know it can be painful, but I’m not going to be a virgin forever, and there’s literally no one I would want to help me through this than you, my very best friend and my dearest love.”

“Okay Ally, I understand that, I have condoms but what about the birth control, and don’t you want to make it special? Maybe dinner first, or something?”

“I don’t want you to use a condom. You’re clean, right” He nodded, “So I am. I don’t want anything between our skin, at least not the first time. I’m not on birth control, no, but I have a Plan B pill in my dorm, just in case.” he gave me a knowing and inquisitive look, “Don’t worry, I am okay to use it. I’ve decided it’s not against my personal beliefs. I believe in a woman’s right to choose, and I choose to use that pill! And tonight is special. It’s the night you told me you loved me and the night I felt truly loved for the first time in my life. If you’re okay with it, I want it to be tonight.”

“Okay, as long as you’ve thought this through.” he said. “We’re going to take this slow, though, and lets go into the bedroom, and let me at least light some candles and put on some music.”

Dylan grabbed my hand and led me to his bedroom. He had a queen sized bed with a black comforter on it and a Dali painting hung above the bed. He sat me down on the bed, still holding my hands, kissed me quickly, and got up to get some vanilla scented candles from the closet. He lit them and set them up all over the room, then he grabbed a yellow towel from the bathroom and laid it down on the bed. “In case you bleed” he said, with a worried look. I nodded. He went to the nightstand and pulled open the bottom drawer. I caught a glimpse of some sex toys and raised my eyebrows. He noticed and chuckled, “we’ll have a lot of fun in the coming days, Ally” he said knowingly. He rooted around and pulled out some lube, “Just in case, to make it easier.” I laughed out loud at him and said, “Dylan, I can orgasm multiple times. I’m so wet right now I’m almost sliding off the bed! I don’t need lube tonight.” He shrugged and set it down on top of the nightstand.

Then he crawled onto the bed, his cock a bit softer than it was, and patted next to him. I scurried up next to him and snuggled into the crook of his arm, giving his chest little kisses as I did.

He turned toward me and said, “Well, alright, lets get you all lubed up, my angel” And he pushed me onto my back, pulled my legs up to his face, and dove into my pussy again.

As he was feasting, he slowly lowered us both down to the bed and reached up with both hands to fondle my tits. That was all it took and I started quivering in climax. He inserted his fingers into my vagina and didn’t seem quite satisfied with the level of wetness, so he climbed up next to me, licked his fingers, and expertly inserted them into my vagina. He kissed my lips so I could taste what he did – such a turn on! – and then he started to suck and nibble my tits while he worked his fingers in my g-spot, sometimes going deeper to try and stretch me out in preparation for him. I started to pound me with his fingers, getting lost in the rhythm, and I started to grind back against him, moaning with unspeakable pleasure under his seasoned hands. I came again, hard and long.

“Are you ready, my love?” he asked.

“Definitely! Fuck me!” I said.

He grabbed the towel and put it under my bum, then kissed me long and deep and positioned himself over me.

“Tell me if it hurts at all, okay.” I nodded, and he started to press his hard cock inside.

“Have you ever had sex with a virgin before, Dylan” I whispered into his ear as he moaned deeply.

“No. Female friends have told me about it, but I never have. This is a first for both of us.”

Being so thick, he couldn’t press in very deep to start with, and slowly rocked back and forth, pushing a little bit further in with every thrust.

“Oh my God. Ally, you’re so tight! It feels incredible. Holy shit, woman!”

It did feel incredible! He hadn’t reached my hymen yet, and it was all I could do to not just shove the rest of him deep inside me, but I waited.

He pressed further in and there was a sharp pain. “Ow!” I said and he stopped the pressure.

“Okay babe. How do you want to do this? Quick like tearing off a bandaid, or slow?”

“Quick! Just push through and get it over with.” And before I could second guess myself, Dylan plunged his thick, throbbing cock deep inside of me.

“RRRrrrrrr” I said, as the pain hit it’s peak. “Fuck!”

“are you ok?!” he asked, concerned.

“Yeah, I’m fine. It just stung like a bitch! Damn! I’m glad I only have to do that once!” I laughed, and he smiled.

We stayed like that for a few minutes, and then I said, “Okay. I’m ready” and he started to slowly work in and out, looking me in the eyes to make sure I was okay. The pain had subsided. I was still sore, but more than that, I was starting to feel incredible pleasure, like nothing I had ever experienced with fingering. It felt incredible to have him fill me up and I started to push my hips up against him.

“Oh my god, Dylan, this is amazing! Fuck me harder!” And Dylan made he patented primal grunt and started to slam me harder, then he started to flick my tits with the tip of his tongue and the pressure in me built. I started to moan louder than ever. I could feel my orgasm out on the horizon, building slower than ever. It was like watching it come towards me from afar. I revealed in it! The desire to climax became torture, and I started to buck against him.

“Oh God, Ally, you’re gonna make me cum if you do that”

“That’s because I’m about to cum, Dylan” and he doubled down and went for broke! His cock got rigid inside of me and I reached a whole new level of pleasure. He reached over and tweaked my nipple and I crested, screaming loudly (thank god we weren’t in my dorm!). The orgasm lasted forever! And it was like I my pussy wanted to devour him. The more I came, the more I thrust him deep inside of me and he lost it. He came hard and loud deep inside of me and it felt amazing! After he thrust he last bit of cum inside, he collapsed ontop of me.

“Dear god, Ally. I had no idea sex could be so intense!” I was breathless. I’d never had an orgasm like that. It was the best thing ever.

I could feel him getting soft inside of me, and our juices dripping out and down my body onto the towel. I had never felt so loved or so satisfied in my life. When he got some energy back, he pushed himself up onto his elbows and kissed me gently and deeply. Then he pulled himself off me and gently cleaned me with the towel, and blew out the candles.

“Was there blood?” I asked as he crawled back into bed.

“No much. A little bit.” He said as he crawled back up and wrapped me into his arms.

“I can’t wait to do that with you again,” I told him. “And I can’t wait to try everything with you.”

“Me, too.” He said. And we fell asleep.

We had sex twice more that night. Once in the middle of the night and again in the morning, but I’ll save those for another story :-)

Source: reddit.com/r/gonewildstories/comments/i5rc2x/fm_how_i_met_the_ta_who_took_my_virginity