So this is the third part of my deflowering story (originally posted on r/gonewildstories).
Part 1: Kinda losing my virginity – https://www.reddit.com/r/gonewildstories/comments/qua13l/kinda_losing_my_virginity_at_26_mf/
Part 2: Actually losing my virginity at 26 – https://www.reddit.com/r/gonewildstories/comments/r06erf/actually_losing_my_virginity_at_26_mf/
Part 5: Getting handcuffed – https://www.reddit.com/r/sexstories/comments/rli84f/getting_handcuffed_for_my_birthday/
(For those too lazy to read parts one and two, Lucy, my girlfriend and I, finally had sex about 3 weeks after we started dating. She probably would’ve jumped my bones on the first night, but I had issues being a virgin and a small 3.5 inch dick, so I inadvertently teased her for three long weeks.
The scene is us, exiting the shower after our first fuck.)
“Umm, so what am I going to wear tonight?” I asked.
“How about nothing?”
“Umm, I’m not sure I could do that … I might catch a cold.” While that’s not entirely untrue, I did catch one the last time I tried sleeping naked, but mostly I tried to decline because the head of my circumcised penis just rubs against the sheets and I get raging boners. Given I had just cum that might’ve been a little uncomfortable.
“Just for a little bit?”
“Ok.”
She grabbed my hand, and led me back to the bed where not so long ago I had, finally, lost my virginity. We each picked a side, and I tried to find a pillow to my liking. As we did this, I became very self conscious of my body and my tiny dick. I tried not to look down, but I feel it shrink beyond its usual 1 inch size, buried mostly by my unkempt pubes and pointing straight ahead despite completely flaccid.
Every now and then I caught of glimpse of Lucy as she got ready to hop into bed. She looked a picture of perfection: confident and sexy, with her butt and tits gently swaying around.
Finally, I climb into bed after her, uncertain of how close to be to her, and whether I should lie on my back or side. In the end, I’m settle on being on the edge of my pillow, on my back, right next to her. I slide my arm under her neck and bring her close. She turns to her side, facing me, one of her legs slightly over mine, her chest and breast brushing my sides, and her pussy just millimeters away from me.
I glance over, “I hope I was satisfactory tonight.”
“You were more than satisfactory. I invited you to stay the night, didn’t I?” she replied, stroking my hairless chest.
I didn’t believe her entirely. I still had a huge hang up about my dick, and I was probably inside her for no more than a minute. I don’t know how long I was lost in my thoughts, but she broke it by kissing me and suggesting we get dressed.
Eventually I found myself in her largest t-shirt, and loosest sweatpants. Lucy climbed into bed wearing just underpants, and a t-shirt that barely covered them up. I was semi-hard again just thinking of what lay underneath and her nipples rubbing against her shirt.
She switched off the light after we climbed into bed. Again Lucy was on her side, hand on my chest, and neck under my arm. Lucy’s breathing soon settled into a slow, steady rhythm. My arm slowly became numb, and I tried to gently wiggle it free, but no luck. I wiggled a little harder, hoping she’d move of her volition, but, again, no luck.
“Hey,” I mumbled.
No response.
I didn’t want to wake her up, but I also couldn’t let my arm go completely dead, so I quickly moved up and out. She muttered something incomprehensible, and snuggled in tighter. My arm was sticking out at weird angle, but at least it wasn’t being rested upon.
As tired as I was from my limited sleep during our weeks of foreplay, and as drained as I was from drinking and finally losing my cherry, I couldn’t fall asleep as my mind was racing.
In that sleepy fog, my thoughts became a soup of joy, and insecurity.
My heart raced and my dick grew stiffer every time I reflected on the last few weeks together.
The feeling of her lips meeting mine, our tongues flicking against each other, the first time I touched her skin under her clothes, touching her wet pussy lips, feeling her lips part as I positioned my cock head at her entrance, the warmth, tightness and sheer sloppy wetness as I slid into her, the image of her biting her lower lip as I slid my short one in and out, the feeling of her wet pussy lips on my leg, her lying naked before me as I tried to get my dick in, the wet sloshy sounds from her pussy as I thrust into her, and her pants of satisfaction after she came on my leg.
Worries that she would soon grow unsatisfied with my small cock, that our sex would grow stale and boring, that I could never truly satisfy her, that I wouldn’t ever last for more than minute or two inside her, and that I never really enjoy the thrill of ejaculating soon deflated my cock and brought me back down to Earth.
I drifted in and out of sleep all night with this beautiful creature lying beside me. As the first morning light crept into the room my worries shifted to whether I would get any rest tonight, but I needn’t have worried: tiredness finally won out and I fell asleep.
When I came to the room was quite bright, the door was ajar, and the smell of bacon was wafting in. I rubbed my eyes, and slowly proceeded into the open plan kitchen/dining area.
Lucy was standing by the stove, eating from a stack of pancakes, still in her “pajamas” from last night.
The thought of bending her over and fucking her did flash across my mind, but I was too much of a gentleman to attempt such a maneuver. Plus I was tired and hungover.
“Good morning, sexy,” I finally said.
“Oh, hi you,” she said, turning around. “Sorry, I couldn’t wait,” she continued as she sucked a bit of maple syrup off her index finger. Damn, she must’ve known that was incredibly arousing.
I glanced at the clock. “Shit, sorry, it’s already one o’clock.”
“Don’t worry about it. It’s been a long few weeks… and we were up late last night.”
I went over to give her a good morning kiss. Our lips and tongues touched, and Lucy tasted so sweet from the maple syrup. As the temperature rose, and my hardening cock began grazing against her, she pulled back.
“Wait. I need to get the bacon out of the oven.”
With her oven mitts on, in an instant Lucy rescued the bacon before it turned from perfectly cooked to burnt.
As the air filled with freshly cooked pig bits, we put aside our lust and ate breakfast instead. Afterwards we mulled over the Saturday newspaper (remember those?), and made small talk.
When Lucy disappeared to the bathroom, I decided to make myself useful by washing the dishes. I nearly dropped the cup I was carefully cleaning when she wrapped her arms around my waist and bit my ear gently.
“I do have a dishwasher, you know.”
“Oh, it’s okay. I prefer to wash by hand.”
“You can use your hands for other chores.”
“Like what?”
“Well… the bed hasn’t been made.”
I finished up whatever I was washing, took off my gloves, and turned around to face her.
“There are other things I could do with my hands that could also be helpful for you, I suppose.”
“Like…?”
I put my hands on Lucy’s hips, and slowly inch my right hand under her shirt, up her sides, and cup the bottom of her breast.
“Like this.”
“Mmm… it’s nice, but it’s not that helpful right now.”
I cup her breast a little firmer, and trace my index finger in ever shrinking circles around her nipple before finally giving it a light flick.
“Is that helpful?”
“Mmm hmmm, but my other breast needs help too.”
After performing the same trick on her other boob, Lucy whips her t-shirt off, showing off her perky breasts and her proud, erect nipples.
Instinctively I bend down and plant my tongue on the outer part of one tip. Again I trace ever shrinking circles around her lovely small orbs before reaching her nipple. After a few gentle flicks, I switch to a mixture of sucking, kisses and flicking.
“Oh god. The other one, please.”
I comply willingly. As I’m sucking on the other nipple, one hand begins wandering down her tummy before running over the top of her panties.
“Wow. You’re really wet. Should we make use of the bed before I fix it?”
In seconds, she’s on her bed and we’re making out with me on top. Although my erection is desperate to escape my clothes, I arch my back so that it doesn’t rub against her body. As much as I want to feel her body against my cock, it’s super sensitive right now and I want to make this last.
Suddenly I feel her hand on my crotch.
“Oh my god. You’re hard,” she says rubbing my member through my pajamas and underpants. Lucy moves her hand away and slides it through the top of my PJs. Now I can feel her sliding her hand along the underside of my length.
The mixture of her warmth, the rubbing and the feeling of the material is sending me horribly close to the edge, so I back away.
“I want to play with it. You’re super hard.”
“It feels so good it could burst soon.”
To make up for the fact that I won’t let her play with my cock, I quickly move my face down to her breasts and begin circling, sucking and flicking her nipples again, making super sure that I pay equal attention to both of her boobs. Lucy moans in appreciation.
After a bit, I begin spider walking a hand down to her panties. I slide my hand underneath, move past her completely sodden pubes, and begin sliding my fingers down the side of her wet lips.
Her moaning grows louder, more ragged as I make out with her breasts and rub the outside of her vagina.
Finally, I slide my middle finger over her clit and into her hot, wet, sticky, smooth sex.
Lucy’s moans have turned into pants and groans.
“I want you in me,” she demands.
“No, I want you to come first,” I reply as I continue finger fucking her.
“Take my panties off.”
Promptly I whip them off and bury my head in her snatch. I lick her lips and her slit, but I’m still not a fan of the taste, so I focus on her clit.
Her moans, groans and the twisting of her hips urge me to continue even when I feel the slightly unpleasant sensation of her pubic hair on my tongue.
In the middle of bucking and weaving, she commands me to kiss her. As I straddle her and move my face back up to meet hers, I glance down and see Lucy cross her legs and move a hand to her clit. As we French kiss, she gyrates against her crotch against her hand.
At the point of orgasm our kissing pauses, as she lets out a deep “ohhhhhhh”.
With Lucy still in the reverie of her orgasm, I lay down to her and gently kiss and nibble her shoulders. In the filtered light of the bedroom I study her soft, largely hairless skin, and stare at her small breasts and hard nipples as they gently rise and fall with her breath.
“Oh my… That was good… Now it’s your turn. How do you want me?”
I straddle her, with my legs around her waist. As I tower above her, I take take off my shirt, and Lucy fondles my member, which goes from being 80% hard to very hard indeed.
Pulling my pants down a fraction, she free my rock hard cock, but leaves the pants uncomfortably pressed against my balls. As much as I hate the sensation of having my balls pressed back like this, it prevents me from popping my load as she strokes my cock.
I was hoping that the slight hangover, and the fact that we had fucked about 12 hours ago would make my cock less sensitive, but no, all these feelings were quickly becoming overwhelming.
“Where’s the condom?” I ask, breaking the moment, and giving me a minute to calm down. I fetch one from her drawer and standing beside her bed, I struggle to get the packet open, and then struggle even more to get on my dick.
“Let me do it for you.”
I climb back onto the bed, and hover my dick (sticking up at 45 degrees to my body) inches from her face. She expertly pinches one end of the condom, and rolls it on.
Between her legs now, and holding my dick at its base, I brush my head against her bush, searching for her slit, I thrust a few times pushing either up over her mound or below into her butt cheeks before I get it right.
Finally I press my head press through her lips and feel her heat. Pushing on through, and there’s a sloppy, sucking sound as I bury myself as deep as I can. Lucy arches her back slightly, tilts her head backwards a fraction, and lets a sexy “oooh”.
My dick lingers there inside her for a beat too long as I savor, again, her tight grip, her smooth walls, and the fluid leaking out from her and onto my balls and pubes.
Keeping in mind she likes it slow, I methodically withdraw and enter her, trying to make sure I use as much as my length as possible. Lucy fondles the bottom of her breasts, and take breathes dramatically through her rounded lips. This vision plus the grip and friction has my cum on the verge of bursting out within 5 strokes (it could’ve been 10 or 15, but all my mental strength was being used to keep it in).
Suddenly it’s too much, and I withdraw completely. I’m panting, counting sheep, thinking of an email I should’ve sent on Friday afternoon. After I don’t know how long, she asks, “Is something wrong?”
“Yeah, you’re too amazing, I’m about to come.”
“Just come, then.”
“No, it’s too soon,” I plead.
“I want to feel you come inside me.”
As she begins reaching down to grab my dick, and put it back inside, I scoot down and begin licking her pussy again. Damn it, I want this to last, I want her to enjoy our sex, I want to keep thrusting into her, but I need to calm down.
I do all the same things I normally do downstairs: lick around the lips, tongue her clit, finger her lips. It’s kinda working, but I’m not getting the same response as before, so I stick my finger in.
Lucy begins to writhe around a little more. That’s better.
“Ooooh, I want you back in me.”
“But I am…”
“No, I want YOU. I want your cock. Please.”
Damn, she makes a convincing argument. Having managed to stuff the cum genie away, I (semi-)reluctantly head back in, and this time I’m able to slide my short one into her on the second attempt. As I break through her lips, Lucy’s eyes roll back and I’m almost instantly overwhelmed by her grip and wetness.
I try going faster this time, and she’s up for it. Our skin is slapping together, her pussy and my dick make sloshy gurgle sounds you just don’t hear on porn, and our breathing becomes ragged. This faster pace, strangely, doesn’t feel as intense for my cock, but about 15 strokes in and I’m already teetering on the point of no return.
Do I withdraw again or do I press on? I press on, and two strokes later it’s all bursting forth into the condom, but again I pretend like nothing’s happening and keep thrusting in and out of her. It’s taking all my mental effort not to stop, and maintain the rhythm.
Instead of feeling the wonderful elation of ejaculation, my brain is taxed with the effort to keep on going. As I keep on keeping on, waves of regret wash over me. I feel shame that I can’t last longer in her, and I feel shame for not being able to accept that and at least enjoy my orgasm.
Shit, now I’ve got to pretend to come to end this charade. Dramatically, I thrust one more time into her, as deep as I can, and moan “I’m coming” as I collapse onto her.
I lie there feeling her breasts against my chest, her legs wrapped around me, wondering how long I need to stay like this.
Kissing her ear, I whisper, “You were amazing.”
“You’re a bit of alright too.”
Hmmm. Did she see straight through my ruse? Is this our last time together? What does that mean?
As I slowly withdraw from her before I’m totally soft, she holds the condom on the base of my dick so it doesn’t slide off and stay inside her. Lying down beside her, I stare the ceiling, and wonder what we do next as my limp one inch dick and its sheath lie against me and drip her juices onto my skin.
Finally, we head off to the bathroom together, and share another shower. I’m still in awe of her body, and the fact that she genuinely wants to have sex with me. She enjoyed it enough to ask me to stay the night again.
I almost turn her down because I’m worried about how funky my underwear is beginning to smell, but she insists that it’s time for her to do a load of laundry.
After dinner we snuggle together on her couch, trying to find something good to watch on TV together. We finally stumble on an inoffensive movie, and during one of the commercial breaks our casual making out gets a little serious.
My hands start wandering around under her t-shirt, and soon enough I’m grabbing her orbs and circling her nipples.
Lucy pushes me on to my back, and whips off her t-shirt. Oh gods, what a view.
“Do you think we should break our couch cherry?” she asks as she strokes my rapidly stiffening cock. Within seconds it’s bucking, straining, and lurching to get out. Having already come twice in the last 24 hours, my cock is hard but also feels depleted and tired.
“I think you know the answer,” I say before she rubs my shaft again. It jumps slightly telegraphing my thoughts entirely.
She licks around my ear lobe, down the nape of my neck, and then manages to sit me up slightly to take my shirt off. She then continues to lick down my chest, then around my nipples, and towards my belly button leaving a cool, wet trail of saliva. With butterfly kisses she works her way downstairs.
My hard cock is resting flat against me and she begins to kiss the head through my pajamas.
“Please stop.”
“Why?”
“I’m close to coming.” Again I was hoping all our recent sexual activity would make me last longer, but my tired dick seems intent on making up for lost time.
Without missing a beat she tucks his fingers into my pants and within seconds I’m lying naked before her with my small but hard cock, pubes and all there for her to see.
Lucy grabs the top of my shaft, stands my cock perpendicular to my body, and pushes the pubic hair down.
Straining my neck, we make eye contact as my head goes between her lips and my cock slowly disappears from view.
My mind is struggling to comprehend what it’s feeling. There’s the sensation of her soft lips sending a circle of pleasure down my shaft, and her wet, sloppy, breathy mouth and tongue on my cock. Then there’s the view of this beautiful angel working her way up and down my cock, and the feeling of her many strands of hair brushing against my legs, hips and pelvis.
After just a few strokes it’s almost too much. I try counting sheep, thinking about work, and in the end I beg her to stop.
With a pop my dick falls out of her mouth. I close my eyes and tense all my muscles to stop my seed to gushing forth as I feel the cool air hit my wet, rock hard member.
After I calm down slightly, Lucy asks me if I want to come in her mouth or in her pussy. I choose the latter, and without ceremony she take her pants off, and grabs a condom and rolls it down my dick. Holding it upright, she straddles me and guides my short thing into her.
I’m still not sick of the feeling of my head parting her lips, and then entering the promised land with my shaft gripped tight inside her hot, wet sex, and her entire weight on my hips.
Opening my eyes I drank in the beautiful sight of Lucy, her cute face, her petite frame, her perky breasts jutting out.
“Don’t you want to come first?” I ask, afraid I won’t be able to muster up the conviction after ejaculating to make her come.
“I just want you.”
She slowly raises and lowers herself on my dick, moaning softly and breathing rhythmically. I thought I wouldn’t last long given how close I was during her blow job, but with her on top and in full control of her pleasure, being inside her wasn’t as uncontrollably intense.
With my dick sticking straight up, and its usable length about 3 or so inches, it wasn’t too long before I slipped out of her.
“Are you enjoying this?” she asks
“I really love this. Are you?”
Lucy nods and sighs as she puts me back in. Soon enough, though, I fall out again. After we achieve re-entry, Lucy shifts from going up and down on my dick, to keeping me fully inside while she rocks backwards and forwards.
Not only does mean I don’t fall out, but the clitoral stimulation really gets her going. To be honest, it felt a little uncomfortable as I had never experienced so much weight rocking backwards and forwards on my hips and pelvis before.
Also when she rocked back, it meant my cock was facing downwards slightly, which given how incredibly stiff my member is when erect, hurt slightly. Nonetheless it was exhilarating seeing her enjoy my dick so much.
After a minute or two Lucy arches her back, cups her breasts and tweaks her nipples before falling forward. I could feel her sex tighten around mine, her legs trembling a bit. The rocking was over, and soon things begin to loosen up around my dick.
“Did you come?”
Without answering her pussy squeezes my hard dick. This sets me off, I grab her delicious butt and begin pumping away at her like an animal.
I expect her to ask me to slow down or stop, but after a little squeal of surprise, her heavy panting and breathing encourage me to keep going at it. Like in the afternoon, this faster pace is less intense than the soft, sensual sex we had last night.
As I approach my climax, I slow down to fully absorb the wonderful feeling of being inside her. The slow sensation of sliding into her is too much, so I withdraw partially and slam into her one last time.
I let out a loud, guttural moan before I finally enjoy the pleasure of feeling wave after wave come out of me and into the condom.
When I calm down from the high of orgasm, I let my hips sink into the bed and bring her butt down with me. The friction of my cock and her pussy moving triggers a twitch from my 3/4 hard dick and one more shot of jizz is let go.
Feeling my spasm, her pussy contracts and squeezes my dick, setting off another twitch and a smaller load of cum.
“Oh god, that was amazing. You’re amazing,” I blurt out.
“You’re not bad, yourself,” she says as we lazily and sloppily make out.
With my dick still at half mast we disentangle our dirty bits. Lying down next to me, she runs her fingers up my wet, cream-filled latex-covered shaft and mutters, “You look like you’re ready for another round soon.”
Source: reddit.com/r/eroticliterature/comments/u7kldl/maybe_she_actually_doesnt_mind_my_small_cock