This is the story of the first time I had sex with my ex-girlfriend. At the time of this story I was 25 and my ex was 20. Obligatory blurb saying that I’ve lurked on the sub for a long time but this is my first time writing a story like this, so bear with me. Slow burn story leading up but it’s my story, so I’ll tell it how I remember it all coming together. If a jerk/jill is what your looking for, sexy times under the ***** Criticism is welcome.
I had known Anya most of my life. She was my uncle’s (by marriage) brother’s adopted daughter. I would see her at the occasional family gathering but didn’t really interact with her much as she was five years younger than me. A little bit Anya and I. Anya is a cute white girl, standing about 5’2”, shoulder length brunette hair at the time, 115 lbs soaking wet with runners legs and quite possibly the best pair 34DD’s I’ve ever had the pleasure of handling in my life. I’m all around average, 5’9”, black hair, 180 lbs and a slightly growing gut after getting out of the Navy.
It all started one day in April of 2012 when I got a text from my uncle telling me that Anya was visiting her boyfriend in San Diego, where I was living at the time, and if I had some time available to hang out with Anya before she went home to San Fransisco. I said sure and he gave me her number to get in contact. I shot her a text and shortly we had plans to grab some lunch at a local pizza joint. She had flown in, so I went to pick her up from her boyfriends house. Coincidentally her boyfriend had gone to high school with me. He was out working at Target, so Anya was hanging out alone in his apartment.
I picked her up and we exchanged a hug. We shared some small talk on the way to the pizza joint. Mostly about how we hadn’t seen each other in awhile, how much we had changed and the like. We got to the restaurant after about ten minutes and went inside. After we got settled and ordered, things began to take a turn. Have you ever been on a blind date and can’t quite seem to make a connection? That was the atmosphere between us while we waited for our food. Conversation seemed all but lost until I discovered that she liked playing video games.
Once this fact was gleamed, it completely upended the atmosphere. We went from awkwardly sitting in half silence to animatedly chatting about our favorite games (hers and mine: Skyrim and Call of Duty), systems of choice (her: Xbox 360, mine: PS3) and who could get who’s butt at CoD. Our food came, conversation continued and before we knew it, it was getting close to the time her boyfriend was getting off work and we needed to head back to his place. I paid the bill and we started the quick drive back.
Anya had accidentally locked herself out when she left earlier so I stuck around till he got home. We shared some pleasantries and explanations on how everyone knew each other. Her boyfriend headed inside while Anya and I said our goodbyes and promised to keep in touch. “That turned out to be a nice day”, I thought to myself as I drove away. Unfortunately she lived a half a state away and even though we had promised to keep in touch, I wouldn’t hear from Anya until several months later.
Summer was just coming to an end before I would hear from Anya again. She texted me out of the blue one September day. We texted back and forth for awhile before she told me the big news. She had broken up with her boyfriend around two months after I had last seen her. I offered her my condolences for the breakup and even though it had been some time since it had happened, I asked her if I could do anything for her. She responded by saying that “A friend to talk to” was enough. Thus began a daily texting habit between the two of us.
Our text chains were light and easy. We talked about everything and nothing. I was probably texting Anya more than I was talking to my roommate. Occasionally the tone would turn flirtatious but never for long. It was mostly played for laughs but as time went on, I was beginning to notice that it was becoming more frequent. Everything would change after the most mundane of events.
After a month of constant texting, at the beginning of October, I had a dentist appointment come up for a cleaning. Anya and I had already been texting since that morning. As I sat in the parking lot waiting for my appointment time, I brought up the upcoming dentist visit. I’ve never had a problem with the dentist and I honestly don’t remember conveying any sort of worry about it. Anya responded by sending me a text saying “Here’s something to keep mind off of it”. What followed blew my mind.
After a minute or two, a new message came though. I opened it and the contents shocked me to say the least. Anya had sent me a selfie. It was shot from the neck down and there she was, topless, wearing only a pair of purple panties. I was stunned and instantly hard. She was beautiful. By the time I came to my senses, I realized my appointment time had come. I responded with a meek “Oh my” and that I had to head in for my cleaning. Anya responded with “Enjoy” and I headed inside. It took all of my willpower to not sport an erection while sitting in that dentist’s chair.
I spent the entire cleaning thinking about it. Why had she sent that? What did it mean? What was I going to say? I only grew more anxious as the cleaning came to the end. As I left the dentist, I sent her a message letting her know I was done. Anya responded back quickly, asking me if it was okay that she had sent me that picture. I responded in the affirmative and asked what it meant. Over the next hour or so, Anya explained to me that she had enjoyed her visit with me months prior and that after she had broken up with her boyfriend, she had developed a crush on me. Our reconnecting and constant texting had solidified it. Anya asked me how I felt about it. I was surprised but eventually responded by telling her that I liked her as well. A whirlwind would follow.
The rest of October was a wild month for us. We were texting even more than before and our relationship began to develop. Since we both had iPhones, we began to FaceTime each other everyday. Then one day I had a great idea. During one of our FaceTimes before bed I asked her if she would be willing to try some mutual masturbation. Anya was shy at first but eventually came around. She agreed that it would be sexy and hopped off her bed.
Anya started first by propping up her phone and began to do a strip tease. She slowly began to remove her shirt, revealing her tight flat stomach and eventually a plain sports bra. Next came her sweats. Anya swayed slightly as she hooked her thumbs into the waistband and slowly revealed the same purple panties she had been wearing in that first picture she had sent me. I was entranced. She continued to sway as her sweats slowly sank to the ground. As she stepped out of them, she crossed her arms and began to pull her sports bra off. As her breasts came into view, I stuck my hand into my shorts and began to slowly stroke myself.
Anya’s breasts were a magnificent sight. Perfectly round, full and perky. Her nipples were small and barely protruding from the surrounding oval shaped areola. I couldn’t wait to put them in my mouth I thought as I continued to stroke myself. I hissed as Anya slowly smiled at me through the video as she hooked her panties and dropped them to the ground. She raised her arms in the air and struck a “TADA!” pose, followed by a little twirl. I laughed as she hopped back onto her bed and readjusted her phone.
Now it was my turn. I rather un-sexily removed my shirt and shorts. Clad only in my boxers, I slowly peeled them off. My erection sprang free and I could see a look of appreciation on Anya’s face. I’m fairly average at six and a half inches but have some girth to it. Clothing removed, I hopped back on my bed and resumed leisurely stroking myself. We complimented each other on our respective bodies and then got down to business.
I watched in awe as Anya groped her breasts with both hands for a while before slowly snaking a hand southward. She spread her legs slightly and I got my first good look at her vagina. She was shaved smooth. Her lips protruded slightly from her labia, with a slightly visible clitoris. Even at a distance and through the video, I could see a sheen coating her. Anya was just as turned on as I was. She started to massage her clit before using two fingers to spread her lips open. The pink color was inviting and I began to stroke myself faster. She traced her lips with her fingers and resumed massaging her clit. The only thing you could hear was soft breathing and the sound of fingers rubbing moist flesh.
Anya closed her eyes and sighed as she sunk a finger into her vagina. Quickly it was joined by a second. Her pace and mine began to pick up. We each continued masturbating and observing the other as time passed. When she began to massage her clit with her other hand, I could feel myself getting close. I could tell Anya was close too, as I watched her movements become almost frantic. She whispered “I’m coming” and it was a wonderful sight. Her head and back arched as her climax overtook her, legs shaking slightly. That was it for me and I spent myself onto my stomach.
We lay there, savoring the moment for a minute. I got up and excused myself to go quickly clean up. I returned to my phone to see her putting on her shirt and sweats, underwear still on the floor. We talked about the experience and agreed that it was definitely something that we would do again. As I put my clothes on and we got ready for bed, I told Anya I had one more thing to tell her. She almost fell off her bed when I told her I had bought her a plane ticket so she could come spend Thanksgiving with me in San Diego.
The next month was filled with sexy pictures being traded and more mutual masturbation sessions. We agreed to be boyfriend and girlfriend. Thanksgiving weekend couldn’t come soon enough, I thought as I went to college and work. Anya and the upcoming visit were all I could think about. It was driving me crazy. Finally, after time seemed to stretch, the day finally came.
I drove to the airport the morning of Thanksgiving Eve. My stomach full of butterflies. I parked and waited for Anya to text that she had arrived. I stewed in my anxiousness until the message came through, “I’m here”. I headed inside to find her. I searched for her before hearing female voice shout “Mat!” from behind. I turned around to see Anya half sprinting towards me. She was dressed casually in a V-neck shirt that showed some cleavage and jeans. One look at her and all the anxiousness melted away. I wrapped my arms around her in a bear hug. We stayed like that for a moment before she tilted her head up, stood on her tiptoes, and kissed me for the first time.
The kiss was urgent but soft. We stood there in the baggage claim looking “that couple” for a few moments before slowly breaking apart. As she stepped back, I could see a flush of red on Anya’s cheeks and she looked up at me and said “Hi”. I said hello back and laughed to myself at the situation. I grabbed her hand in mine and we started to chat while waiting for her bags to appear. Once her bags showed up on the carousel, we grabbed them and headed out to my car. Bags loaded up, I drove away from the airport hand in hand with Anya. Everything felt right.
As we drove away, Anya asked me what we were going to do with our day. I told her that we were going to go visit the USS Midway, a aircraft carrier turned museum. I asked her if that was ok and she said “As long as its with you, I up for anything.” Blushing, I drove us to our destination. We arrived at the Midway shortly after noon. I paid and we walked up the gangway to the museum. We explored the ship at a slow pace, reading placards and taking in the sights. There weren’t very many visiting that day, so at times we were alone in sections of the ship. This led to me getting handsy with Anya.
As we entered a section of crew quarters, I checked to see if we were alone. Satisfied we were, I reached out and groped Anya’s butt. It was small, proportional to her frame, and firm. Anya squealed and jumped a bit. I laughed as she swatted my hand blushing. As we continued to explore, I grew bolder. In one room I pulled her into a hug and stuck my hands into her back pockets. In another, as Anya read a placard, I reached under her arms and cupped her breasts over her shirt. In an officer quarters section, I pulled her onto a berth and we made out for several minutes. All of this action had me aroused and it was getting awkward walking around sporting a constant erection. I decided it was about time to get out of there.
We left the museum around four and I took her to a taco shop for a late lunch. Stomachs satisfied, it was time to head home. The drive back to my apartment was quiet and the anticipation of what was coming was starting to get to me. Lost in my thoughts I almost missed my exit but made it last second. And then we arrived. I got her bags out and we headed inside. I gave her a tour of my two bedroom apartment that I shared with my roommate, who was thankfully not at home. I showed her to my room and got her bags put away.
We stood in my room for a moment, silently contemplating each other. Anya made the first move. She walked up to me and pulled my head down for a kiss. I reciprocated by gently pushing my tongue past her lips. We caressed each other as we lost ourselves in the kiss. After a few minutes, we broke apart. As Anya leaned back against the frame of my king sized bed, I gave her a peck on the lips and started pulling her shirt over her head.
*****
Anya’s bra was blue, lacy but conservative. Her cleavage was inviting and I stuck my head between her breasts and breathed in. She smelled lightly of lavender. I reached behind her and unhooked her bra. I took a step back as she pulled her arms from the straps and covered her nipples with her arms as the bra fell to the ground. Anya blushed and I gasped when she dropped her arms to reveal breasts in all their glory.
I gently took hold of the left and then the right, feeling them unobstructed for the first time. They were heavy in my hands and soft to the touch. Her nipples were beginning to show signs of arousal, stiffening at my touch. I took her left nipple into my mouth and began to lightly suck on it. Anya let out a soft moan as I circled her nipple with my tongue and squeezed her right breast. I could tell her nipples were a spot to pay attention to. Hungrily I pushed forward until Anya was lying on the bed with her legs handing off the side.
Momentarily sated, I stood up and took in the sight. Anya, lying on my bed topless, hair splayed out like a fan underneath her. I had never seen something so beautiful. She blushed as I appraised her silently. I leaned forward to kiss her again before reaching to unbutton her jeans. Since her legs were off the bed, Anya only had to raise her butt a little as I pulled her jeans off. Her panties matched her bra. The were bikini cut, blue and lacy. I leaned forward, planted kiss on her mound and pulled her panties down as well.
There she lay, in all her naked glory. As I pulled her panties from her ankles, I began running my hand up her calves slowly. I planted kisses on the inside of her thighs as I rose up. As my hands reached her thighs, I gently pulled them apart. Anya gave slight resistance and then allowed me to spread her legs, exposing her pussy to me. With the spreading of her legs, her lips had opened for me as well. They were glistening in the light, just like when we had FaceTimed what seemed like ages ago. I caressed her legs around her pelvis as I knelt on the ground and tasted her for the first time.
Anya tasted sweet. To this day, I’ve never tasted one so sweet. Anya shivered as I licked from her from perineum to clit. She gasped as I suckled her clit and gently nibbled it before resuming my exploration of her folds. Anya grabbed my hair as I pushed my tongue into her increasingly wet hole. She wrapped her legs around my head as I continued to tongue fuck her. I heard an almost inaudible pleading sound of desire when I removed my tongue and then a content sigh as I replaced it with a finger. Her vagina was impossibly tight and gripped my finger, as if not wanting to let go. I curled it up towards her g-spot as I began to thrust in and out. We continued like that before I felt it had been worked up enough and stuck a second finger in. This one went in easier but was gripped just as tight as before.
With the second finger in, I began to suck on her clit again. My forehead smacked her stomach as her back arched from the stimulus. “Keep going”, Anya hissed, as I looked up towards her. I did just that. After a few minutes I switched hands fingering her and used my now slick free hand to grope her breasts and then massage her perineum. I began to circle her anus and then slowly put pressure on the hole. I felt a hand on my head slightly push and Anya whispered “Not today”. I pulled my finger away and continued my assault elsewhere.
After what felt like a special forever of tasting and fingering my girlfriend, I could feel her getting close. I renewed my efforts on her clit and pinched her nipples. She thrashed against me and came. Her legs tightened around my head as her orgasm rolled through her. I continued to finger her slowly as it subsided. Utterly relaxed, my head was freed, as her legs fell to the side of the bed. Knees groaning at me in pain, I stood up and leaned over to give Anya a kiss. Her eyes went wide and she started to giggle. I asked her what’s so funny and she said go look in a mirror. I walked to the bathroom as she giggled some more. I checked myself out in the mirror and laughed myself. I looked like I just drank a giant hot chocolate, except it was Anya’s cream around my mouth. We both continued to laugh as I cleaned myself up.
As I returned to the bedroom, I marveled at the situation I was in. Just two short months ago, Anya and I were just texting buddies. Now here I was, a naked Anya lying on my bed, who I had just eaten out and I was still completely dressed. It dawned on me that I was a very lucky man. If I had ignored my uncle that day, none of this would have happened. I laughed to myself as I took off my shirt, dropped my pants and boxers in one swipe, and hopped up on the bed to rejoin a waiting Anya.
Climbing across the bed, I half sat against the pillows and headboard. I pulled Anya close and we started to make out again, sitting next to each other. As we made out, Anya’s hand ran up and down my chest, arms and stomach as she got a feel for me for the first time without clothes. Slowly her hand motions trailed further and further south until her fingertips lightly brushed my shaft. Her delicate fingers encircled me and began to stroke up and down. I broke away from our kiss to moan my appreciation of Anya’s attention to the erection I had more or less been sporting the whole day.
Anya’s small hand around my shaft almost made my cock look bigger in comparison. Her pace quickened slightly as pre-cum began to lubricate her hand. She began to sink herself lower against my body while jerking me until her head was near my waist. Anya leaned over and gently planted kiss on the tip of the head of my penis. Then she withdrew just enough to stick her tongue out and lick her way around the tip. I groaned as she opened her mouth and began to take the head into her mouth. She took about half of me into her mouth, lips tight around my shaft. Anya pulled back, my cock not quite leaving her mouth before sinking down again. She continued to blow me until I could feel I was approaching the point of no return.
I reached out and gently pulled her away from my aching cock. I sat up and laid her on her back. I crawled between her legs and took up a perch above her. As my cock grazed her lips, I looked Anya in the eyes. She stared back and then nodded almost imperceptibly. I took my cock in my hand and began to rub her lips with it. After several passes her lips began to spread, the head of my cock glistening with her arousal, I slowly pushed the head into Anya’s waiting hole.
As I inexorably pushed forward, Anya cooed. I had never felt a vagina so tight. Her walls gripped my cock tightly until finally I was completely inside of her. I leaned forward and kissed her as I began a slow withdrawal. Anya moaned as my cock left her, pining the loss. My head back at her entrance, I pushed forward again and began a steady rhythm. We kissed some more before she wrapped her legs around my ass and pushed me into her harder. Encouraged, I started pumping into with more vigor. The sound of my balls slapping her ass filled the room as I drilled into her depths.
As I kept pace, I reached out to grope her right breast. While fondling it, I leaned over and took her left nipple into my mouth. The flesh tasted clean and sweet. I pressed down on her right nipple, which elicited a gasp from Anya. I pinched and pulled as I continued to maul the left. I leaned back, tugging on both nipples as I did. Anya’s legs tightened around me and I could tell that she was close. I leaned forward again, placing my hand behind her back. I pulled her upright and laid back. She shuffled her legs and we were in a cowgirl position. As we moved I could see my shaft covered in her white cream. I once more took her exquisite breasts in hand and mouth as I began to jackhammer my cock into her.
A few moments of that was all it took. Anya cried out as her orgasm shook her body. Her vagina gripped my like a vice. I slowed my thrusts, half from her vagina locking on, half from being slightly winded. As Anya rode the waves of her orgasm, I pulled her ear to my lips and whispered, “Can I come inside you?” She gasped back, “I’m on the pill” and that’s all it took. With one more thrust, I began to shoot my semen deep into her vagina. I gave a few more half-hearted thrusts as her vagina milked my cock. I pulled Anya with me as I collapsed onto the bed.
We lay there, still connected, lost in a post-sex haze. Eventually I shrank out of her. I could feel my semen leaking out of her and onto me, so I rolled Anya off of me. I went to the bathroom to grab baby wipes and tissue to clean up. Anya lay on the bed, eyes closed with a smile on her face, as I returned. She jumped a bit as I gently cleaned her up, her vagina still sensitive. Cleanup complete, I threw out the wipes and got back onto the bed to snuggle with Anya. We lay there holding each other tight until we fell asleep.
We woke up two hours later to growling stomachs. We got up and agreed that we needed to eat. I lamented watching her dress, I never wanted to see her in clothes again. But alas, food called so we finished dressing and left to go get food.
Thanksgiving came and went. Anya helped my roommate and I prepare dinner. I introduced her to my friends. We left the apartment a few times that weekend but never for long. We couldn’t keep our hands off of each other for longer and always headed back for another round. We had sex like rabbits that weekend. Sunday came and it was time for her to fly home. The drive to the airport was quiet. We didn’t know when we would see each other again.
As we got to the airport and I pulled her bags out of the car, Anya began to softly cry. I felt the same but managed to hold it in. I walked her in and stood with her as she checked into her flight. We hugged each other until it was time for her to go through security. I tilted her head up and kissed her. We gripped each other tightly, not wanting to let the other go. She pulled away and looked up at me. Eyes still misty, Anya said “I love you”. I whispered back “I love you too”, gave her a peck on the lips and spun her around. I lightly slapped her ass and gave her a gentle push towards the security line. She laughed and got in line. I stood there watching her go through the line. When she got through Anya turned and waved at me. I waved back and started to walk back to my car.
It wouldn’t be terribly long before I saw Anya again. I traveled to San Jose to visit my parents for Christmas. We were inseparable the entire time. She would hitch a ride with my parents when they came down to visit for Easter. The second they showed up, I took Anya to the bathroom and had sex with her on the counter. Anya would move in with me shortly after. That would be the true beginning of our relationship.
Source: reddit.com/r/gonewildstories/comments/kc6o80/my25_first_time_having_sex_with_my_exgf20_anya
Why’d u break up tho