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The Day I Didn't Lose My Virginity

Posted by: Author: Age: 35 Posted on: 6 comments
5 likes 5701 views Category: Masturbation Male-Female Tags: first time, caught, grinding, aroused, cum on tits, facial

The only thing that was better is the day that I did.


When I was 18 my friend, Greg, invited me to spend about 10 days with him at the beach, a good day's drive away from our hometown. Going on this trip would be me, Greg, his little sister Tiffany, her friend whose name I now forget, and their mother, Jane. who was 41. Pretty sure you can tell where this is headed. Jane was the archetypal hot mom, and everyone in my circle of friends fantasized about her, and it embarrassed Greg whenever we would bring up her body and her looks. Having been a long time friend of the family I'd stolen my share of glances at Jane in her bathing suit, filling my rampagingly horny mind with dirty, nasty thoughts, and more than once I'd had to stay in the water while my erection subsided. Also fueling my fantasies others' too, I'm sure was the fact Jane was a nurse. Although it never happened we all secretly hoped she'd have to give us a hernia check during our physical exams for the football team.

Of course, being just a few weeks shy of my 19th birthday, I was masturbating upwards of three times a day just to relieve myself of the unfocused sexual tension, not to mention the seemingly limitless semen, that welled up inside me every day. However, at the beach, sharing a room with Greg, this was not an option. Greg and I were friends, and we joked about stealing porn magazines and jerking off, but it's not anything we'd ever do together. By the sixth day I was about to jump out of my skin, I was so horny. Jane wasn't helping, but it wasn't her fault. I would spy her amazing, huge tits bouncing in her swimsuit or breezy sun dress and nearly groan; I'm not sure if I really wanted to fuck her or if I just wanted to see her naked and jack off, but my mind was going deep into an uncharted realm of fantasy and lust that, unlike just looking at Penthouse or Playboy, Jane was real, and her body was amazing, a perfect hourglass figure with double-D cup breasts I know because I had seen her bra while rooting for a pair of panties to sniff during a sleepover. Jane was always well made-up, with red lipstick, painted fingertips and large, glamour sunglasses, sometimes pushed up over her big, feathery hairdo. Walking down to the beach in her suit, Jane wore strappy sandals that clacked on the boardwalk, setting a sexy beat to the sway of her hot ass, the strap of her beach bag looped in the crook of her arm.

On this sixth day, I decided I couldn't stand it any longer. I decided to make up a wardrobe malfunction while swimming simply sliding my drawstring all the way inside its tunnel, so that there was no way for me to remove it and tie it. Gripping my waistband, I told Greg I had to swap for another pair of trunks or fix these, so I was going back to the condo. He said go for it, and I headed for the building. I didn't tell Jane why I was leaving because it wasn't necessary.

Once I was out of sight I was sprinting for the room, knowing that every second they didn't notice I was gone was a second I could put toward my self-pleasure. At the front door, I have no idea what came over me, but I suddenly got the urge to masturbate in Jane's bed. I had a couple of techniques then, one of which was to spread my legs in a kind of frog posture and hump the mattress, grinding my dick into it and pretending I was fucking whatever woman was in my fantasies at the moment. (The technique also allowed me to masturbate and turn the pages of a porn magazine at the same time.) Thus, inside the condo, I beelined for Jane's room, got under the covers, and dropped my trunks to my ankles. Since I wasn't supposed to be fully clothed, I felt like I would be safe, I could just pull my trunks up and pretend I was looking for something in the bathroom if someone came in the door unexpectedly.

Underneath the soft covers, I imagined laying next to Jane in bed, what it would be like to press my cock into her hip and cup her huge tits from the side. I ground my cock into the mattress, wanting to rub it all over anything that touched Jane's pussy and naked body. My gyrations became more pronounced, more sexual, acting out the rhythm I had seen in X-rated movies. I rolled my hips, thinking about pumping my cock between Jane's swaying big tits and coming all over her face.

At this point the air conditioning came on. I mention this because the fan inside the condo was quite loud. (This was hot beach weather in the South, after all). And I had closed the bedroom door behind me, because it opened up into the living room, and one could see inside easily. With the air conditioner on I started moaning louder and breathing more heavily; I've always been vocal in both sex and masturbation. Still fantasizing about what it would be like to plunge my cock inside Jane's pussy. Was it bushy, like the models in the magazines? Would she spread it for me? Would she grip my cock and flick the tip of her tongue out at my cockhead? Did she give blowjobs? Did she like to be fucked doggystyle? Would she let me cum on her face? In her mouth? I made up mental images to answer all of these questions with a "Yes." I raised up, still grinding the mattress, the covers slipping off my back and exposing my ass. I felt my orgasm welling up. "Yeah, Yeah!!!! Gonna cum! Yeah Ms. Hollaway, gonna shoot it for you!!!" I gasped. Out it surged, several hot streams spattering the mattress. I took several deep breaths, and then my thoughts immediately turned to cleaning up my cum before it left a stain. I slipped off my damp trunks to blot it up and then

"What? What are you, Oh God" Jane said from behind me. My face was instantly hot with shame. What had she heard?! What had she seen?! I turned to see her standing there, arms at her sides and mouth open, stunned. Jane waved her hand in the air and turned to leave. "Put some pants ... never mind, just get out of my room."

I don't know that I have ever felt that mortified in my life. I couldn't face her. I even tiptoed to my bedroom because I didn't want there to be even the sound of my existence in her mind, that's how embarrassed I was. I quietly closed the door and lay on my bed, awaiting my fate.

In a few moments there was a knock on the door. "I'm going back to the beach, are you coming?" Jane said, and I heard her go "Oh, shit," under her breath, maybe realizing her double entendre.

"No," I croaked. "I can't right now."

"Are you OK?" Jane asked.

"No," I said.

"OK, I'm gonna give you some time to get your thoughts together," she said. "Shape it up, it's not the end of the world." I heard the condo door close and she was gone.

I just lay there on my bed, trying to force myself to have a blank mind and not think about what had just happened. I'm not sure how long it was, but I heard the door again, and someone standing outside the door. A million thoughts raced, the worst of which that it was Greg, and he somehow knew about this. But it was Jane.

"Look, I've told Greg that you got sick and threw up, and you're in here napping," Jane said. "So why don't you come out here and we can talk about what's going on." She opened the door. I was surprised to see quite a sympathetic look on Jane's face.

We walked into her bedroom, the scene of the crime. She sat in a chair across from the bed and I sat on the corner furthest from the spot I'd humped. I felt like crying; what she had to say would determine whether I did or not.

"Alan, all young men masturbate. All older men masturbate. Women masturbate. I masturbate. It is nothing to be ashamed of," Jane said. "You know. You know what's going on with your body right now. You're not making all of this ... stuff just so you can get one woman pregnant 10 or so years from now. But I want to talk with you about this, because I know some really screwed up things can happen if you are ashamed of your sexuality, if you can't accept it.

"It's not that you acted on it at the wrong time," she said. "You just acted on it in the wrong place. And you got caught, but you didn't know. I think the worst thing that could come out of this is if you become so embarrassed of your body that you don't act on your sexuality when you should, when you are with a young woman who," and she smiled warmly, "will be a very lucky woman when that time comes."

It put me totally at ease, but I still couldn't find the words. I took a deep breath. "Ms. Hollaway, I am so, so sorry to have ... done ... that," I said. "I would never think about you ... as ... I don't think you are ..."

"Alan, stop," she said gently, and sat on the bed beside me. "It's alright. I know I am not a slut. And I know I'm not a pornstar. And I know you're a good guy. Good guys can have fantasies, too, you can't pick who or what turns you on. There's something about me that excites you, that's all. And that's really not my business, actually," She put her hand on my shoulder, "Your body and your fantasies are your property, no one else. No one can tell you what to do with them, no one can tell you what they are, no one can tell you to stop."

"Thank you," I said.

"Now, what can we do to make this alright, because we've got another four days together, and I don't want this to be awkward for me, or painful for you, and I certainly don't want Greg or Tiffany to have a bad time because things are weird," she said, matter of factly.

"I don't know," I said.

"Do you want to masturbate with my panties?" she asked. "I'll be glad to give you a pair."

"No," I said.

"What do you want to do right now," she said. "It's up to you."

"I want to fuck you," I said.

"Well," Jane said, "that's not going to happen. I'm married, and you're 18. It's grounds for divorce." But the way she said it led me to believe she would fuck me otherwise.

"Would you ... would you watch me?" I said.

"No," Jane said. "I'm not going to do anything with you naked or with me naked. That's more grounds for divorce."

There was a long pause, and Jane changed the subject. She asked how I masturbated, because she'd never seen a young man do that before. I told her why I adopted that pose, and what it allowed me to do. "So it allows you to feel like you're having sex," she said. "You're going to have great technique when you finally do." She wanted to be sure she wasn't my only fantasy. Oh, no, I said. Not at all. I gave her names Heather, Kimberly, Kathy, Nicole, Missy, and even my previous teachers like Miss Jenkins.

"Why did you want to masturbate in my bed?" she asked. Drawing a deep breath, I told her if I couldn't fuck her I wanted to rub my penis all over her, and if I couldn't do that, I wanted to rub it all over the bed where she lay naked; but mostly, I wanted to do something more than just masturbate by myself with thoughts of her.

"OK," Jane said. "I have an idea."

Jane told me to go into my bedroom and put on a pair of underpants. She said I should make sure to give myself an erection, first. Jane said she would be laying on the bed in her one-piece swimsuit. She said I could come in and with my underpants on and with her suit on grind and rub all over her "until you get it out of your system."

"Deal?" she asked. I stammered in the affirmative and went to my room. I didn't have to touch my dick, it was instantly hard. It pulled the waistband a good inch-and-a-half away. I walked into Jane's bedroom, proud of my penis and how big it must have looked. To me, anyway. I climbed on the bed and rolled over to her side.

"Now get on top," Jane said, and I straddled her stomach. She looked over her large, pillowy breasts at me. "Now you can do what you were doing on the mattress."

I lowered myself onto her stomach and began rubbing her with my crotch, gently at first, then more firmly. I gripped the top of the headboard so I wouldn't crush into her, just gently stroke her through the fabric of my underpants. My cock nearly poked through the top of my waistband. The leg holes were stretched out, she could no doubt see my swaying balls.

"You can talk dirty," Jane said. "That's fine, that's not naked sex."

"Um," I said.

"Do you want to fuck me?" Jane asked.

"Yes," I said. "I want to fuck you Ms. Hollaway."

"Go on," she said. "This is your fantasy, you only get to do this once. You can say anything."

I told her I wanted to fuck her hot pussy, and fuck her big tits. She asked me how I would do that, and I told her she would squeeze her tits together while I stroked in between them. I told her I wanted her to jack me off and suck my cock until I came in her mouth. It probably didn't sound very sexy, but it was everything I had seen in porn to that point, and I wanted to do it with her.

I was grinding my crotch into her tits now, a huge dot of pre-cum spreading on my trunks. Jane was reaching down, gripping my ass lightly, pulling me into her. "Does that feel good?" she asked. I told her yes. She spread her legs. "My pussy," she said, and I moved my crotch down and began grinding it into hers. She began grinding back, undulating. I looked at Jane her eyes were half closed, mouth slightly open. She was panting. I looked down to see my dickhead wedged between my stomach and the waistband, pre-cum leaking from its head, grinding my shaft into her soft mound. I felt Jane's hand on my cheek, looked up, and we kissed.

My humping started going faster, on instinct, as we held the kiss, tongues exploring each other's mouths. Pulling away from her, she sucked on my lips. I continued grinding and groaning. Jane looked at me with a devilish smile, "Yeah!" she gasped. "Yeah! Oh, God you fucking stud! Oh, fuck me, my horny stud!" In a flash, Jane's hand was inside the leg of my underpants, springing my cock free. Jane then grabbed the straps of her swimsuit and freed her amazing big tits. This was the first time I had ever seen a woman's breasts in real life. And now, Jane was commanding me to

"Cum all over these big tits, Alan!" she said. "Cum on! You know you wanna!"

I got off about two quick strokes before the cum started surging out in a hot, white fountain. The first stream went right up between her tits, hitting her on the chin and lower lip. The second exploded about a millimeter after it left my dick, splattering her face. The third streamed into her bangs. By the time it was all over, I had cum all over Jane's face; very little of it had landed on her tits.

Almost immediately we set about to cleaning up. Jane wiped the cum from her face with her fingertips, then went into the bathroom with a washcloth. I wiped my dick on her pillow and got up from the bed, with a wave of confidence coming over me like never before. I literally felt like a man for the first time, with my lover in the bathroom after a hot round of passionate sex. I walked up behind and grabbed her ass manfully. "Wow!" Jane said. "Look at you!" I stood behind her, kissing her shoulders, as we looked in the mirror to make sure all the cum was out of her hair, laughing as we did so.

Only 20 or so minutes had elapsed. Jane told me to wait in the condo for another 45 minutes or so, just to make it look like I had really been sick. She was going back out to the beach to make sure everything was OK there.

The next day I lost my virginity to her, on the couch of the beach condo.



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