A little background before we get to the good stuff, I (22M at the time) grew up in a very religious, very sexually repressed household. That at least partially (the religion, not just the repression) contributed to my lifelong struggle with depression and anxiety. To this day the anxiety can still inhibit my performance in the bedroom, but this is a story about one time a few years back when I let go of my inhibitions with the lovely lady (25F at the time) who helped me work through them.
I know the backstory will be a little long, so for those of you who want to skip to the good stuff, scroll to the second —– break.
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When I met her (we worked together, I’d been there for a while when she was hired,) I wasn’t at my best. I was depressed, miserable at work with management that mistreated me badly, still getting over the messy end of a “thing” with another girl that I wouldn’t say counted as a proper relationship, and struggling with my physical health on top of all that.
She saw the sadness in me, and made sure to comment on the good moments, like when she caught me smiling down at my phone because my brother sent me some dumb joke. It allowed me to live in those good moments for a while longer. We started talking, and I felt comfortable with her, talking about the hard parts of my past that I don’t usually open up about. I felt like she really cared about me, and felt intimate with her in a non-sexual way.
Management changed for the better, my health improved, and we grew closer. I loved talking to her but never tried to make a move (I’d rather not screw up the friendship, it was good for me) until one night we were out driving, talking, and she asked “when are you gonna fucking kiss me?”
So yeah, things built from there. I wasn’t a virgin, but definitely inexperienced. Low single digit body count and never more than 3 times with the same girl. She was more experienced, having had a long committed relationship where she explored her sexuality. And knowing my past she wanted to give me that same opportunity to explore with her.
We tried a lot of stuff, cautiously at first because I was still apprehensive. I mean, I have a healthy male sex drive, and I wanted to have new experiences. But due to my upbringing sometimes I was too anxious to go through with new things, or even perform at all. She was respectful of this, and very caring. Often some less vanilla moments, and more rarely even vanilla sex, were cut short and she would just hold me close and whisper sweet reassurance in my ear. Sometimes this would relax me enough to try again, and she slowly, lovingly, expanded my comfort zone. Sometimes it just wasn’t right for me and we’d have regular sex, and other time I was too anxious to do anything but cuddle. And she never guilted me for it, even if it was something she loved.
And of course the emotional intimacy remained, building even further. She was my confidante, my lover, my friend. She taught me how to love myself again. The relationship built up my confidence, improved my depression, and eased my nerves. I wasn’t just being taken care of, I was taking care of myself, forming good habits to keep myself physically and mentally healthy.
I tried my best to be as good to her as she was to me. She was new to the area, so I showed her all my favorite places, the beaches, the coffee shops, the nature walks. I loved to cook for her, food has always been a passion of mine. And I did my best to attend to her needs too, emotionally and physically. But the way I felt so cared for, I don’t know if an equal return was possible.
One thing she knew she liked, and wanted to try with me, was exhibitionism. Now, I was getting more comfortable one on one in the bedroom, and I did like to watch that kind of porn sometimes, but there was no way I was ready for that! In particular she mentioned having sex on the beach as something she’d done in the past.
There were some gorgeous beaches in the area, and we liked to go often. Sometimes we’d just swim and sunbathe, other times I’d feel more confident with the PDA and we’d make out on a towel. Frequently we’d go in the evening, dressed a bit warmer than swimsuits, to watch the sunset or stargaze. On these nights she liked to start grinding on my leg or my bulge while we kissed, and she would usually make herself cum this way. I loved watching this, hard as a rock beneath my jeans, but never took things further until we’d retreat back to my car and fog up the windows.
Now to add some visual description for you. I am 6′ even, 160 lbs at the time. Arms and legs a bit disproportionately long for my height. Those legs were and still are very well built from years of soccer, hockey, and long distance cycling, and I have a fantastic, full and firm butt to match. I have slight stretch marks on my thighs and ass from the time I grew 6 inches in one summer. A less impressive upper body, pale and lean but not quite lean enough for abs, and a wide-shouldered frame that at the time still needed a few more year’s work to fill out right. I have thick, straight brown-black hair, that was shoulder length at the time. A pretty average, cut, grower dick that, when erect, is 5.5 inches with reasonable girth. And my favorite feature is my eyes, intensely dark blue that pierce your soul if you stare into them long enough.
She was 5′ nothing, and yes, the height difference drove me crazy. Probably 115-120 pounds (I never asked) with soft 32D breasts, beautifully pale with clear tan lines, ending in light pink gumdrops, with just a bit of faint areola. A nearly, but not quite flat stomach that accentuated her curves nicely. A nice round, soft ass, and just the right amount of meat on her thighs. A pretty pussy, a deeper pink than her nipples, with small, neat lips, and a landing strip. Long, wavy hair that went about two thirds of the way down her back, and changed color every month or two. Looking back at pics from that month, she was blonde this time, with dark roots just starting to show. A cute face, with naturally plump lips and round cheeks. And hazel eyes, with just a bit of gold in the middle radiating in a star pattern from her pupils. I thought she was a bit out of my league, but hey, that’s for her to decide!
—–
One day I looked at the astronomical calendar and saw that the peak of the Perseids meteor shower was coming in a week or so. It was supposed to be great viewing, with the peak coming just a couple days after the New Moon so it wouldn’t disrupt the show. So I asked her if she wanted to watch it with me. Of course she said yes, and we made plans to arrive before sunset so we could watch that too.
She told me to bring a blanket, which I knew meant she wanted to try for sex. A towel is too small, you’ll get sand everywhere you don’t want it, and she’d told me about this the first time we had talked about sex on the beach. A blanket gives you more space to work with. So I chose a heavier one from my bed, one that should stand up to the sand well, about king-sized, and washed it the night before.
I stopped by her house to pick her up that evening. As I got out of the car she came out the front door and I was absolutely stunned. She had her hair in a messy bun, and she was wearing a loose, flowing sundress, as bright red as her lipstick. It ended about 3 inches above the knee, and my eyes worked their way down to brown gladiator sandals that were tied halfway up her calf. She was carrying a brown canvas beach bag the same shade as the sandals. The dress was sleeveless, with a deep scoop neck that stopped maybe an inch above her front bra strap.
Or it would have, if she was wearing one. As she drew close I could see the faint outline of her pokies, and she was trying to walk like a model, both feet walking the same line and moving her hips just enough to start her tits jiggling. They swayed back and forth, daring the dress to give way and reveal her, before going back the other way, teasing me.
She knew what she was doing, it was *on.* She was starting visual foreplay well in advance, trying to make herself irresistible so my desire would overcome my anxiety. She wasn’t taking no for an answer tonight. After what seemed like 10 minutes but in reality was mere seconds of me staring at her perfect figure, she was there in front of me. She went up on her tiptoes for a kiss, so I took her bag and leaned down to meet her lips. I could smell her perfume, an intoxicating vanilla and some other, more subtle notes I couldn’t quite identify. She reached her arms around my back and grabbed as much of my ass as her tiny hands could hold. Fuck.
I pulled away and opened the passenger door, trying to be a gentleman. She got in feet first, leaning down towards me in just the right way that the loose fabric pulled away to give me a view of her nipples for a second. I could feel myself growing, pressing against my tight jeans.
I put her bag in the back seat, on top of the folded blanket, and got in the driver’s seat. She grabbed my hand as I drove, resting it on her thigh, then began running her fingers through my thick hair until I told her stop. I needed to focus on the road. I did steal a squeeze of her boob as I brought my hand back to the wheel, though, and she giggled mischievously.
We got to the beach parking lot, and the weather was perfect. High 70’s/low 80’s, just the slightest breeze, and not a cloud in sight. It was an hour before sunset, so the sun was just starting to tint the sky orange. As I went to step out of the car, she pulled me back in, so I sat down. She asked for her bag, so I reached into the back seat and brought it to her. From it she produced two nips of rum (I think “nip” might be a regional term? It’s those one shot bottles.) and handed me one. I don’t normally drink in public but I knew she meant for it to be a dose of liquid courage, lowering my inhibitions. We drank.
We walked out to the beach. I remember it was right around high tide when we arrived. It was still a little busy, and I knew her intentions, so I anxiously scanned the area for children. There were none, just some couples and a few larger groups. We walked down the beach to find a somewhat isolated spot, a hundred feet past the last couple with empty sands beyond. There were large dunes behind us and the sea in front, so if anyone saw us it would be from one direction only. This helped me relax.
We laid out the blanket, removed our footwear, and laid back side by side to watch the sunset. The sand beneath the blanket was supportive, but not uncomfortably firm. She was already starting to get handsy, running her hands through my hair, along my arms and chest, relaxing me but keeping her hands above my hips to avoid heightening my nerves. I could feel that and the rum both loosening me up, not buzzed, not off one shot, but just present enough to do the job.
I was kissing her, confidently, comfortable enough with that level of PDA by now and eager for the taste of her lips. Not non-stop, the kissing was interrupted by light conversation and taking moments to gaze at the sky, now much more orange… Or at the light’s reflection in her gorgeous eyes. I was feeling good.
When the sun was a few degrees above the water, I grew more bold, touching her breasts over the dress, then reaching under for direct contact. She took this as a sign that it was time to escalate things, and pushed my shoulders to the ground, which I willingly accepted. She climbed on top and started kissing me in sort of a reverse missionary position.
By this point I was hard, once again straining against my tight jeans, but my mind wasn’t quite there, distracted by the possibility of getting caught. My heart was going well over 100 BPM. She felt this, her chest against mine, and asked if she should keep my pants on for now. This put my mind more at ease and I agreed, comforted that she was willing to move at my pace.
She tucked the front of her dress between her legs. This made me suspicious, so I ran my hands around the outside of her dress, along her hips, down her round ass, and then her legs and confirmed – no panty line. She wanted something between her pussy and my jeans, not the best fabric for grinding against. She later told me she chose that sundress because the material was quite comfortable up against her parts. The tease show she used it for was just a bonus.
She started to grind, slowly at first, as we continued to make out. She interlocked her fingers with mine, and held my hands down above my head. I was starting to get into it, and I wanted to touch her more openly. She could tell, and she was teasing me. Kissing my lips, my forehead, my neck and chest while I had to lay back, pinned.
I sat up, somewhat forcefully, freeing my hands and lifting her weight up. Now I could touch her more freely, and ran my hands over the dress again up her thighs, around back to her thick ass, and up her back. On my way back down I could feel a damp spot growing, her arousal made clear. I mentioned this, and she whispered “of course I’m wet for you” in my ear before throwing me back down with more force than I’d sat up. She wanted to get her rhythm back, but she allowed me the use of my hands this time.
After a few minutes of this I noticed an older couple walking in our direction. She was grinding against my bulge and felt me go soft, feeling my heart rate quicken again. She took my hands in hers, whispered to relax, and stayed where she was, her hips still. We continued to kiss, more gently, hiding the fact that she had been trying to get off. Her calm demeanor transferred to me, and once they had passed we were quickly back into it. She was so in tune with my body and mind.
After another several minutes, growing braver with my hands, her hips moving steadily against me, I could see it in her eyes. That look when her lids were halfway closed, her hazel eyes gazing at my blues, trying to suppress her moans and nearly succeeding, just a bit quieter than the sound of the waves. She was getting close. I pulled her close for a kiss, and as our lips parted I put my thumbs in her mouth to wet them slightly, then reached into her dress with both hands. Her boobs were mine to play with. I squeezed them and teased her nipples with my thumbs, which I knew she liked, and pulled her breasts out of her dress. I could feel my pants grow damp, unsure if it was her juices or my precum or likely a little of both. I was so turned on.
I reached up to put a hand over her mouth in case she screamed, but she moved it away and leaned closer to me. She kissed me passionately, her tongue against mine, then moved to my neck. With her ear right next to my mouth I whispered “I can’t believe how hot you are, I want you to cum for me.” She moaned my name and continued using my body to masturbate with that same steady rhythm.
As she came, she bit down on the base of my neck, HARD. That’s how she suppressed the scream. We hadn’t done any pain play before besides light spanks when we did doggy, but I instantly saw the appeal. Endorphins flooded my brain, sending electricity down my spine, my arms, my legs, and my shaft. Holy fuck I needed her on me.
When she was done, she stopped and pulled a wet wipe from her bag. She wiped a light trickle of blood from my shoulder and then kissed the area gently, sending follow up waves of endorphins through my body. She put the wipe in a plastic shopping bag and asked if I was ready.
I realized now that I forgot a condom. I asked if she had them, but I was the one who always bought them. When she said no I went soft from anxiety. We’d had the STD history/birth control conversation already, deciding on a copper IUD, but we hadn’t scheduled the appointment yet so we had always used a condom. In fact this would be my first time bareback with anyone, excluding oral/hands.
I didn’t trust my pull out game with no experience, so this caused more panic from me. I was trying to remember what I knew about the Fertility Awareness Method, trying to remember the last time her period was, and trying to do math to figure out when she would have ovulated. She reassured me she was due in 3 days and she had a fairly long cycle so she shouldn’t be fertile. She also told me that although she thought it was safe, it was still up to me.
We sat up and talked for a few minutes. I remember around this time the last sliver of sun disappeared beneath the horizon. Still pretty bright with the orange sky above, though. There was a light, steady breeze coming off the water, and I could smell salt in the air. The beach was starting to empty, with the sun fully set. I calmed down a bit, and then I saw that her tits were still out from when I was playing with them. My other head made the decision for me as I felt it pulse to life. I was not just willing, but eager to do it raw despite my reservations.
I told her, but said I need to wait a bit longer to start feeling it again. She pulled another nip of rum from her bag and I drank it. Then she had me lay on my side facing her as she unzipped my pants, so she could play with me through my boxer briefs. I was quickly ready to go.
She pulled my shirt off, then straddled me in a way that her dress would cover what we were doing, and slipped my dick out from inside my boxer briefs. After a few more strokes with her hands she tucked it under her dress and brought me inside.
Oh, fuck that was good. This being my first time without a condom, it had always felt warm, but I was amazed at just how much warmer it was without that thin bit of latex between us. I watched her eyes flutter closed for a moment, such a sexy sight, as she inserted the head, then pressed her hips down further on my shaft. I could feel my heartbeat in my penis, as it grew harder than I thought it ever could.
She leaned down on me in the same position she had been grinding, her tits pressed against my bare chest, and her lips within reach of mine. She started to ride me with that same steady, sensual pace as her previous grind while we made out, her lips moving along mine, my face, and my neck. I could feel the soft fabric of her dress moving against my stomach, and I shivered from the new sensation.
After a few minutes of this, the pressure of my jeans and underwear against my balls was getting uncomfortable. I stopped her, and we looked around at the beach. The sky was now dark above us, with vibrant red and orange on the horizon up to maybe 30 degrees above the water. The rest of the beach was finally empty, and seeing this I eagerly pulled her dress off. I lifted my hips off the blanket as she removed my jeans, then used her teeth to pull my underwear down and off my legs. I stroked my cock watching this, lubricated by her juices and excited to finally see her gorgeous naked form.
She laid down next to me and spread her legs. I got between them and reinserted myself, now deeper into her vagina with my body unrestricted by clothes. We passionately made love in missionary for several minutes. I kissed her lips, her neck, and her chest, tasting just a hint of sweat. Her hands were exploring my shoulders, back, and in particular squeezing my ass, which I loved.
She sat up and asked for doggy. We tried this for a minute, as I struggled to find a good rhythm. Due to the height difference and my long legs we usually needed furniture or a pillow under her knees for this at home. Instead I pushed her hips down, laying her in the prone position. She laughed, realizing I was having trouble, and let the change happen. Then I moved up her body a bit, to get a bit of a downward angle. I gave her butt a few spanks, not quite hard enough to leave a mark, and squeezed it with one hand as I entered her vagina.
My god, this position was tight. I slowly picked up pace, listening to her moans as my head ran against her G-Spot. With each thrust I pushed my hips against her ass, loving the cushion it gave. Supporting my weight with one hand, I used the other to touch her body, softly rubbing down her back and arms.
It wasn’t long before I was ready to orgasm, and she knew it, hearing my breaths get heavier, turning into deep moans, as I vocalized my pleasure. She asked if I was close, and I confirmed. “I’m not done with you yet!” She commanded me to lay down, and I obeyed. She sat down on my stomach, not yet ready to reinsert me.
She rubbed her pussy with two fingers as I touched her, one hand squeezing her ass, the other fondling a boob. I pulled her down closer and kissed her, slowly working down from her lips, to her neck, to her tits, and sucked on the one that wasn’t getting attention from my hand. She moaned loudly as she inserted her fingers deep into her vagina, then removed them, sticky from her wetness. I pulled her hand to my mouth and tasted her, just barely salty and metallic. It drove me wild, my cock begging for her touch.
She moved her hips back over mine, and put me back in her for the last time of the session. I tried to thrust from beneath, but she pushed my hips back down so she could control the pace as she fucked me cowgirl. The way she moved her hips was truly mind-blowing, not particularly fast or slow, but a consistent medium pace, rubbing the front of my dick against her G-Spot on the in-stroke, and pressing the back against the slight ridges of her vagina on the out-stroke. This was something I hadn’t felt before with a condom. Every last millimeter of my head and shaft was being thoroughly stimulated, I couldn’t last much longer.
While she rode she continued to rub her clit through its hood with her fingers, and our moans grew louder. I was fully vocal, no longer nervous now that the beach was empty. I tried to play with her nipples again but lost focus, desperately trying to hold back my cum. My hands settled on her smooth thighs instead, so she used her free hand to touch her boobs.
And then it happened. Her loud scream and my low growl, as her pussy tightened around me, the first wave of her orgasm setting off my own. She tried to keep her riding pace as long as she could as she quivered on top of me, my legs and hips bucking with ecstasy beneath her as I filled her with shot after shot of my cum. I did my best to keep my eyes open, gazing into hers, as we climaxed in unison. Eventually I moved too forcefully, slipping out of her, and the last two contractions of my dick found empty air.
“Holy shit,” I said, louder than I intended. I’d never finished at the same time as my partner before. I had never felt so close to her, overwhelmed by the rush of oxytocin. She collapsed onto me, and I wrapped my arms around her. We stayed there together for another minute, feeling each other’s heavy breathing in our chests, as I whispered how amazing she was. She told me how hard she came, and how proud she was that I could step outside my comfort zone.
She rolled off me and reached into her bag for more wet wipes. She handed me one, and we cleaned ourselves off. We needed quite a few for our combined fluids, and she used another to clean her lipstick off me. She said “I need to pee” but struggled to stand, legs shaking. I pulled myself up onto my knees in front of her to help her up, kissing her breast as it passed in front of my face. This made her giggle and fall back down to the blanket so I helped her up again. We both walked a few yards away from the blanket to pee, in opposite directions, then reunited.
I wanted to cuddle, but with the sun down the temperature was dropping so we dressed first. She pulled the boyshorts she hadn’t worn from her bag, along with some yoga pants. I gave her my hoodie that I carried out to the beach, knowing that she gets cold easily. She zipped it up over her bare tits and stuffed the dress in the bag.
We laid down on our sides, facing each other, legs intertwined as I pulled her closer, her vanilla scent somehow unaffected by our sweat and fluids. I could have spent an eternity there with her, gazing into her eyes, cuddling, kissing, sometimes talking quietly but more often just listening to the waves rolling softly to shore. It was easily the most intimate moment of my life at that point. We stayed like that for a long time, an hour or more based on the flow of the tide going out, only occasionally changing positions to avoid losing circulation in our limbs.
After all that cuddling the sky was fully dark, and we sat up to watch the meteor shower. She pulled out four more shots of rum to split, a couple granola bars, and two large bottles of water, which I suddenly realized I desperately needed.
We sat there watching the skies for a couple more hours, until cloud cover rolled in blocking the view. She turned to me, pulled down the zipper on my hoodie revealing her boobs, and asked, “Ready for round two?”
Source: reddit.com/r/gonewildstories/comments/jaf0t4/mf_how_i_overcame_my_anxiety_and_gave_in_to_my
Great story, great visuals.
I love your writing! Descriptions were very well done
Did you end up marrying her?
Great read and superbly written. Sorry to hear you are no longer together, but glad you were able to find someone who was able to restore your confidence.