At twenty years of age, I was still a virgin. I’d never even kissed a girl. I certainly wanted to, but my lack of confidence prevented me from making any moves.
Depression and mild social anxiety plagued me all my life, and I feared rejection. My horrible self-image sapped any chance in my mind of even a moderately attractive girl falling in love with me.
Truthfully, I wasn’t nearly as ugly as I felt. I was average height, I was not overweight, and I had a decent (if somewhat young-looking) face. But I found myself hideously unattractive, so I believed everyone else did too. Girls could be friends with me, but I didn’t think I would ever get the chance to kiss or have sex.
Actually, there were a few times I had hope. My brief, painful forays into online dating and flirting with girls at parties had begun with confidence. But I eventually realized that even moderately attractive girls had by far the upper hand when it came to selecting men. I was in a wide world of other ugly boys vying for attention, while the cool and confident guys got chosen.
This predicament didn’t fuel some misogynistic mindset within me; rather, it increased my self-hatred. These girls seemed like goddesses, while unworthy-me had no hope.
Often I cried at night, wishing I were dead so I wouldn’t have to live this painful, lonely life without anyone to snuggle up to.
Occasionally my unbearable sadness extended into the day, too. It was on one of these days that I met the woman who saved me.
Sitting on a park bench on a windy, overcast day, I swiped right through Tinder, as I had done last night until I hit the swipe limit. For days I had been swiping, with only two matches, both of whom were bots.
Again, I hit the limit. Again, no matches after a hundred swipes to the right. Frustration overcame me. Without shame, I began to cry publicly.
Lying down on the bench and curling up in a ball, I sobbed and sobbed, hiding my face beneath my arms. At that moment, I couldn’t bear to keep living like this. I so desperately needed someone to hug me, someone to love me, or life wasn’t worth it.
I paused my sobbing. A sweet, feminine voice came from the other end of the bench.
“Why are you crying?”
I peered out. She had a concerned look, and was sitting right beside me. I sat up all the way and tried to wipe my tears.
“It’s nothing. Sorry for bothering you.”
She smiled in a sympathetic sort of way. “Don’t say that. I was just worried about you. I see you at this park all the time, but usually you’re not so upset.”
I gazed over her. She had long, dark brown hair and a face that simultaneously exuded cuteness and maturity. She seemed about my height—maybe ever so slightly taller—and looked to be around thirty. She wore a brown trench-coat and black boots.
“I know we don’t know each other,” she spoke softly, “but I would feel awful if I didn’t ask if there was anything I could do to help.”
Looking at the ground, I sighed. “There’s nothing you can do. It’s hopeless.”
“Do you want to talk about… whatever it is?”
“Trust me, you don’t want to know.”
“Why would you think that?”
“Please, you should just leave me here. Everything is hopeless for me.”
She scooted closer to me. “Well, if that’s how you feel, then I don’t think I should leave you alone. Please, I want to help you. Do you really want me to go?”
Her genuine interest confused me. “No, I don’t want you to go, but I don’t know how you could possibly want to sit on this bench with a worthless pile of shit like me.”
“Did you do something bad?”
“No, no—I’m just worthless.”
I was startled by a sudden feeling of arms wrapping around me. She hugged me tightly, and I felt a calming warmth I’d never felt before. I wanted that moment to never end. But why the hell was I getting her attention?
“You’re not worthless. Please don’t say that.”
I began sobbing again, my tears running down her coat. She continued to embrace me, stroking my back and squeezing me tightly into her soft, fit body.
“If you don’t want to, it’s okay… but would you like to go get coffee across the street and talk about whatever’s troubling you?”
I sniffled. “Okay, sure.”
In the coffee shop, we both got lattes. She insisted on paying. We sat on a secluded, corner couch, warm inside the building. She took off her trench-coat, revealing a very attractive figure. I couldn’t help but notice her shapely but not unnaturally large bosom, and her perfectly subtle curves that gave her just enough shape to look heavenly and soft. Internally, I scolded myself for thinking with my penis.
She made a cute little smile, sipping her latte. “My name is Alexa. What’s yours?”
“Nice to meet you, Kyle.”
“It’s nice to meet you, too, Alexa.”
“So, do you want to tell me what you’re so upset about?”
I shook my head. “I’m sorry. I can’t.”
She frowned. “I’m sorry. Am I making you uncomfortable?”
“No, no. I just don’t think you’d want to hear.”
“Why would you say that?”
“You’d judge me, or think I was weird or some kind of loser or creep if I told you.”
She reached out and held my hand. “You said you didn’t do anything bad, though, right?”
She looked straight into my eyes. “Then I promise I won’t judge you.”
I took a deep breath.
She squeezed my hand. “Tell me, Kyle. It’s okay. You can tell me.”
“Wait.” I looked at the floor.
“Why do you care so much about me? Why are you even talking to me?”
“You looked like you needed help. And, well, you’re kinda a cute guy, and…” she blushed… “You seem like you might be a nice person to hang out with.”
I looked back at her eyes. Alexa’s face wore a look of genuine concern and compassion.
I couldn’t hold myself together anymore. I collapsed onto her lap and began crying again. She bent forward and hugged me again. “Did someone hurt you?” she asked.
I got up and shook my head.
“Then why are you so upset?”
I took another deep breath. “I’m really upset because… because I’m horribly lonely.”
I held back another sob. “This is so embarrassing. I don’t want you to think that I’m hitting on you or anything, but I’ve never had a girlfriend. I’ve never had sex. I’ve never even kissed a girl. And I just want a girl to love me like I love her.”
Alexa put her hand on my shoulder. “Aww, I’m sorry. I didn’t have any idea you were so lonely.”
“I’m sorry for making you hear all that.”
“There’s nothing to apologize for. I’m really glad you told me all that.”
“Really.” She looked out the window, where it was raining heavily. “The coffee shop is about to close, but it’s raining really hard outside. Did you walk to the park?”
“Yeah, I did.”
“Let me give you a ride in my car.”
We walked outside and instantly got soaked. Her car was parked in a lot just down the street.
Her car was a nice, tasteful luxury model. We began driving. This was it, I thought. I opened up to her and now she can drop me off at home, and she’ll never talk to me again.
She turned toward me. “Would you like to come over to my place for dinner?”
My heart jumped. “Sure. Thank you!”
“What did you mean earlier when you said… I was kinda a cute guy?”
She laughed softly. “I meant what I said.”
“But how could you possibly think that?”
“What do you mean?”
“Let’s be honest. There’s no way anyone could say that to me and actually mean it.”
“I think there’s no way anyone could say that to you and not mean it.”
We stopped at a red light.
“Do you like me?”
She laughed again, leaned over and gave me a hug. “Of course I do! Why do you think I’m inviting you over for dinner?”
“I just can’t understand how anyone could like me.”
She looked at me with an understanding expression. “I’m so sorry you feel that way, Kyle. But I want you to know that I think you’re awesome, and I’m sure a lot of people would feel that way if they got to know you.”
After a while, we arrived at Alexa’s house, which sat atop a rocky hill. It was very modern looking, and all white. We pulled into the garage and got out of the car.
“Do you live here all by yourself?”
“Yes, I do. Do you like it?”
“It looks very nice.”
“Come on inside, where it’s warmer.”
Inside it was indeed warm. The smooth wood floors felt good under my feet, and the house was decorated minimally but beautifully.
“We’re both still soaking wet, Kyle. Let me get you something.”
She ran off and returned with one of her bathrobes. “I don’t have any mens’ clothes in the house, so this will have to do. Why don’t you go the bathroom and change into this so you can dry off?”
I took the bathrobe and thanked her.
That evening we ate a simple, delicious dinner of spaghetti and green beans. I was famished and so was she. Sitting across from each other at the dinner table, we mostly just ate, rather than talking.
After dinner, Alexa invited me to lie down on the couch with her. I couldn’t believe what was happening, but I was totally unsure about Alexa’s intentions. Did she just want to cuddle with her new friend, or was she sexually interested in me? Was she falling in love? I couldn’t imaging her being sexually attracted to me—she called me cute, not sexy.
“Is this okay? Do you want to do this?” Alexa asked me as we lay face to face on the massive sofa.
“I do if you do.”
“Great!” she grinned with her ridiculously cute face.
She had changed into a soft, tight pair of pajamas consisting of silky pants and a revealing top with thin straps.
“Kyle, I need to ask you something.”
“Are you sexually attracted to me?”
I froze. She knew what I had been thinking. She had seen through it all, and was going to kick me out of the house now before I did anything dirty and disgusting.
“You are a very beautiful person.”
She swatted me with a pillow. “That’s not what I asked. Are you or aren’t you?”
My heart was racing, and she felt it. “Kyle, I don’t want to make you nervous. If anything, I’m the nervous one here.”
This perplexed me, but I finally spoke. “Alexa, I think you are incredibly sexy, and I’m sorry if that weirds you out, and I’ll totally understand if you want me to go.”
She suddenly started beaming, and practically jumped on me, wrapping her firm legs around me. “I’m so glad to hear you say that!” she said.
I, in turn, wrapped myself around her, and for the first time in a long time I felt blissfully content. Her sweet, natural smell wafted into my nostrils as I breathed, my head nuzzling the amazingly soft skin on her neck.
“See, Kyle,” she whispered, “I know how you feel. You have such a low self-esteem, and it’s tragic, because there are millions of girls out there who would love to be your girlfriend, to make love to you, to be there when you need a hand. But you’re not alone. I used to feel like you do. I felt ugly and unlovable and was sure that nobody would ever want me.”
“But you’re so beautiful!”
“Thanks, but it took a long time for me to feel that way about myself, and to build the confidence to approach men. Even now, I still struggle with my self-image a little.”
I hugged her even more tightly, and she hugged me back even tighter. “So why did you approach me?”
“I’ve been with various men over the years. But I always went with the ones who were confident enough to approach me. And most of those guys were jerks, or things just didn’t work out because we didn’t have enough in common. But then I thought, what if I get a boyfriend who isn’t so full of himself? What if I make the first move? I could reach out to someone who feels just the way I used to, full of self-doubt, and show him that it doesn’t have to be that way.”
“So that’s why you kept talking to me today, even when I acted like a total loser?”
“You’re not a total loser. You’re so, so brave. And I mean that. I honestly didn’t know earlier, when we were sitting in the park, that this would go this far. But when you told me how lonely you were, I also happened to realize at the same moment that I might really like you. If you’ll let me, I’d like to get to know you even better in the coming days and weeks and months and… however long you want.”
“Are you saying… you want to be my girlfriend?”
“Of course I do! If you want me to.”
“Of course I do! I’ve never had a girlfriend! This is so amazing, and you are so kind, and I can’t believe that something so wonderful is happening to me. I feel so happy right now I think I’m going to start crying again.”
We both cried tears of happiness and love, as we lay there, cuddling on the couch, me in her girly bathrobe, and her in her sexy pajamas.
We spent what seemed like hours of bliss, embracing each other in a variety of positions. I loved, loved, loved cuddling with her. There was one issue though—I had an erection that I was desperately trying to keep her from feeling.
Eventually Alexa turned towards me. “Why are you trying to keep me from feeling your boner?” I blushed and she laughed. “You think I’m mad? I love that I’m making you horny. It makes me a little wet, too!”
This was all just too amazing to be real, and she felt my excitement. “Kyle, you realize that I like you, and I know you like me, and I guess we’re even going to be boyfriend and girlfriend now, so you don’t need to feel embarrassed about anything, got it?”
“Okay, but Alexa?”
“Will we… are you… would it be possible… and please don’t get mad at me—”
“Kyle! I’m not going to be mad at you! Whatever you say! And I know what you’re going to say! You need to stop worrying. I told you, you’re making me wet! Just say it, and say it proudly!”
I paused. “Alexa, I want to fuck you.”
She laughed. “Yay! I want to fuck you too!”
I snuggled up to her so that my boner rubbed against her leg, through our clothing. “This is such a perfect day. And to think that earlier, it all seemed impossible.”
She nuzzled against me, and her cuteness nearly killed me with ecstasy. “So, Kyle, do you want to fuck now, or later?”
“Honestly, I would love to fuck you any time, but I love cuddling with you so much right now, and to be honest I’m so tired that I just want to fall asleep with you squeezing my body with your arms and legs.”
She hugged me tighter, and rubbed her crotch against mine. “I’m really sleepy too,” she said. “Let’s go to bed.”
I reluctantly released her and began to get up, but she grabbed me and, to my surprise, lifted me up and into her arms! “I didn’t realize you were so strong!” I said.
“Do I intimidate you?”
“No. I think it’s really sexy that you can pick me up.”
“Don’t cream all over my bathrobe!” she joked, walking into the bedroom and plopping me into her bed.
I pulled back the covers and started to lie down, but I realized the thick bathrobe was uncomfortable to wear in bed. “Just throw it on the floor,” Alexa said as she slid into the other side of the bed.
“But I’m not wearing anything underneath!”
“Then if you get naked, I’ll get naked too, so it’s fair!”
Alexa chuckled once more. “No, the girl who just said she wants to fuck you is uncomfortable with cuddling in the nude.”
I smiled and threw off the bathrobe, revealing my naked body to Alexa for the first time. Immediately I felt shameful and embarrassed for her to see my ugly, naked self. But Alexa’s reaction was anything but disgust. Her eyes looked excited, like a child who’d just gotten a fabulous birthday present. She ran her hands all over my belly, my butt, but not my penis. “We’ll save that bad boy for when we actually fuck,” she remarked with a wink.
“It’s your turn,” I reminded her.
She beamed and pulled off her pajama shirt, then her pants. “I want you to undress me the rest of the way,” she said.
I moved over and cupped her breasts, still covered by a purple bra, squeezing them until she moaned loudly. I crawled around behind her and unclasped her bra, letting her breasts fall free. She turned toward me and I immediately dove my face into them while she giggled. Her breasts were simply the most amazing thing ever. Soft, squishy skin with such delightfully suckable nipples! Her nipples were nice and large enough to get a good grasp upon with my mouth, and she squealed as I massaged her chest with my face and hands.
“Don’t forget my panties!” she said after I had sucked her breasts for some time. I moved downwards, and cupped her vulva through her underwear. I could feel the firm outline of her lips through the dripping wet fabric. Slowly, I grabbed the lace string and pulled her panties down, exposing her glistening, bare pussy, which was leaving a massive, beautiful wet spot on the bed. I inhaled deeply, savoring the scent.
“I love feeling absurdly horny yet content like this at the same time!” I said.
We embraced for a bit more, then Alexa pulled away. “Before we go to sleep, we need to go over a few formalities.”
“What do you mean?”
“I just want us to take the proper precautions about safe sex. We’re sleeping together fully nude, and if we start fucking in our sleep, I don’t want us to have any regrets.”
“First things first, I want you to know that we don’t have to worry about birth control. I have an IUD. Second, we need to talk about STDs. You told me you are a kiss-less virgin, right?”
“OK, so you’re clean. And I got tested after the last time I broke up, so no worries.”
“OK, let’s snuggle up and go to sleep now.”
That night I quickly fell asleep. Alexa spooned me, her front against my butt, her legs wrapped around me and her feet brushing my penis. I drifted off to sleep, and dreamed about cuddling Alexa some more.
I awoke late that next morning. Alexa was no longer spooning me and I thought had all been a dream. Then I heard moaning from behind me.
Alexa was lying on the bed, legs spread, masturbating. She squeezed her pussy lips and rubbed them around, up and down, stimulating her clitoris. She had her other hand fingering her vagina. Turning towards me, she smiled. “Good morning, Kyle!”
“Too horny to wait?”
“I woke up earlier and didn’t want to wake you. I’m almost on my third orgasm!”
“Wow! You must be having a lot of fun.”
She suddenly screamed with joy, and spasmed as her orgasm hit her, juices dripping all over the bed. Flushed and breathing heavily, she licked her fingers and told me to come closer.
“I can’t believe it, but we’ve forgotten something,” she said.
“You haven’t had your first kiss!”
She pulled me onto her mouth and launched her tongue past my lips and onto mine. It was so much fun. I could taste her juices swirling around in our spit.
Gasping, we separated, and then kissed again. Then she got up and told me to eat her out. I kissed the insides of her thighs, licking closer and closer to her lovely paradise. She had me lie down on my back, and positioned herself over my face. I opened my lips wide, she lowered herself, and I enveloped her vulva with my mouth, sucking at it slowly with constant pressure, running my tongue over it repeatedly.
Resting my tongue inside her vagina, I sucked around the area of her clit, and she started to cum in my mouth. Her juices tasted so good. “I could drink you all day,” I said as I released my mouth from her pussy.
“Wait, hold on,” Alexa said. She ran off and came back with something. “This is a latex dam. Do you know what it is for?” she said.
“Yeah, I do,” I said.
“You know, for a virgin, you sure are great at sex,” she said.
“As a lonely boy, I masturbated to a lot of erotica,” I replied.
“I’m going to sit on your face again, only this time I want you to give me a rimjob through this dam. After all, I wouldn’t want you to accidentally eat shit!”
We resumed our positions, and I stuck my tongue all over her asshole. The dam was a strawberry flavor, and I rammed my tongue as deep as I could into her accommodating orifice. After minutes of moaning, she said she wanted to give me a rimjob. We got another dam and I got on my knees and bent over. The feeling of her tongue in my butt was very hot. I loved the feeling of this hot girl ever so slightly penetrating my sensitive hole, and I started dripping precum.
“Since you like this so much, can I try pegging you?” she inquired. I agreed, and she came back with a strap-on and a bottle of lube. Greasing me up, she then slid the toy easily into me, as the base of the strap-on ground against her mound, making her moan softly.
The feeling of prostate stimulation is quite different from stroking my penis. It’s a pleasant feeling to be filled, and I kept wanting more and more, as the penetration made me hornier and hornier.
Eventually, Alexa stopped, pulling the dildo out and setting it aside in a tray on the floor. We then kissed passionately, attacking each other with love, pressing her boobs against my chest, grabbing her ass and rubbing my finger over the opening. She felt so strong, so loving, so nurturing as she pushed me against the bed and smothered me in kisses. I wanted her to take me.
She gave another one of her perfect smiles and grabbed my penis. There was a lot of precum for her to use as lubricant as she began giving me a very slow handjob. But she knew I wouldn’t last long, so she quickly put me in her mouth before I had a chance to jizz all over myself.
The feeling of her lips and tongue slowly slide up and down my shaft was unforgettable. She knew exactly how to rub her tongue on the underside of my penis’s head, till I felt nearly ready to cum. Then she pulled me out of her mouth.
“Kyle, can you cum in my pussy? Don’t worry about lasting long. You’ve already made me cum so much. I just want you to have the strongest orgasm of your life, and fill me with your hot, sticky cum, and then you can suck it out of my pussy, and we can pass it back and forth between our mouths, and then we can smear it all over our bodies, and then we can fuck all over again!”
I pulled her head to mine and kissed her deeply, while she pointed my penis toward her vagina. She slid down onto me, and happily bounced up and down, her big boobs jiggling.
I erupted into her pussy, and the feeling of filling her with my hot cum was incredible. I let her tight pussy walls squeeze my cock, plugging up the jizz inside of her. She collapsed upon me, and we drifted off to sleep. I had no idea how much fun we were about to have for years to come. Even today, we still love fucking each other just as much as ever.