Painters Delight

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Loosing his virginity to an older woman.
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Here is a little story about loosing my virginity. I'm sure time has embellished it somewhat but is basically true.

I was in collage, and very shy. I was looking to rent a room in a house near campus. I had looked at several ads but had not found what I needed. Either the places were dumps or the rent was out of reach. I was about ready to give up and just live in the dorm another semester, but decide to check out one more place. I knocked on the door and a stunning Asian woman answered it. I told her I was interested in renting the room she had listed at the campus center. She laughed a little, and told me that the ad specified that she was looking for a female boarder. I looked down at the ad again and realized my error. I couldn't look her in the eye I was so embarrassed. I made my apologies, and started to leave when she called out after me.

"Hold on." She said, "I was looking for a woman, but you seem like such a nice guy I guess I could show you the room.

"By the way, I'm Sandy" She said holding out her hand.

She showed me the room, and I couldn't believe how nice it was. I asked what the rent was, and again was disappointed that it was out of my reach, and told her as much. She frowned, in a way that was so sexy, and asked if I was good with my hands? Perhaps, we could negotiate the rent if I agreed to help out with some work around the house. It seems she got the house in a divorce after she caught her husband cheating on her. This I found hard to believe as she as really stunning. Anyway, we came to an agreement and I moved in the next weekend.

Things were going really well and one Saturday morning Sandy asked me to help her paint her bedroom. First thing to do was take out as much stuff as was practical. I was moving out one of her nightstands, and had tilted it up to fit through the door, when the drawer slid open and her vibrator fell out and rolled across the floor. I was so naive I didn't even realize what it was at first and just stared at it.

Suddenly it hit me and I must have turned 6 shades of red. I quickly tried to put it back in the drawer, but Sandy saw it and me. I was speechless and stammering for words. Sandy just laughed as said, "My God, you are as sweet as you seem."

She told me it was OK and not to be embarrassed. She told me that although she had been divorced nearly a year, she wasn't ready for the dating scene again just yet. And well, a woman has needs too. I was still holding the vibrator at that point and she asked if she could have it back, unless I needed it that was. Her teasing had me bright red again. Realizing, she had embarrassed me, she asked in a very sweet voice.

"Alex, are you a virgin?" All I could do was nod my head. Sandy took me by the hand, taking the vibrator with her, and led me to sit down on the bed.

"Sorry if I embarrassed you." She said.

"It's OK." I answered with a week smile. I finally had the nerve to look up at her. Sandy was wearing an old white T-shirt and Jeans. Her breasts were not large but her nipples were very prominent and I couldn't help but notice she wasn't wearing a bra that day. Now yes, I was very shy, and a virgin. But I certainly wasn't a monk. Sitting on her bed, smelling her sent, watching her breasts rise and fall with each breath soon had me hard as a rock. I guess I was pretty obvious about looking at her breasts because she then asked me if I thought her breasts were too small.

"No." I stammered, and then somewhat emboldened by my growing desire added, "They look great to me."

"Really?" she smiled. "I've always a little self conscious about them. Especially since the slut I caught my ex with had really big tits."

"No. Really, I think they are beautiful." I replied.

"Thanks." She said, moving a little closer.

"What do you like best about them?" she asked as she pulled the tee shirt tight over them. I couldn't believe how much her nipples were standing out.

"Your nipples" I said without thinking.

"Yeah," she replied, "I've always really liked them too. I know there big for my size but they've always been so sensitive. I really love to have them sucked on." Then with a slight pause she added. "Would you like to suck on them, Alex?"

I don't think I said a word, but I'm sure the look on my face was all the answer she needed. Sandy then stood and turned to face me. She reached down and with one smooth motion pulled the tee shirt off. As great as her tits looked through the thin shirt, they looked even better with out it. After tossing the shirt on the floor, she reached up and tweaked her nipples between her thumb and fingers. Letting out a small moan. She then leaned in to me, her breasts at just at my face level. I quickly, took one of her nipples in my mouth and sucked greedily on it. Her hand reached around my head, and pulled my face into her breast. I couldn't believe how hard and rubbery her nipple was. I would flick my tongue across it and feel it spring back to shape in my mouth. Now I was a virgin, but this wasn't the first tit I had sucked on, (OK, it was the second) but it was definitely the best. I kept moving my mouth from one tit to the other. Loving the feeling as each nipple would pop into my mouth. I don't know how long we stayed that way. It seemed like an eternity, and only a few moments all in one. Sandy then pushed her weight onto me and we both fell back onto her bed. She then sat up and was straddling me. If she hadn't seen my hard-on before she couldn't miss it then. Now I'm no porn star, but I am fairly well endowed, about eight inches long and rather thick. She then leaned forward, placing her hands on either side of my shoulders and started to dry hump me. Mind you, she was still in her jeans and I was fully clothed in an old Journey tee shirt and shorts.

I reached up and pulled her down on top of me. My mouth found hers and we started kissing, our tongues exploring each other's mouths. During the kiss, I rolled over on top of her, her legs wrapping around me as I pounded my hips into her. God I was so hard, it hurt. She then reached down between us and felt the head of my cock that had pushed it's way above the waistband of my shots. She then broke the kiss and said to me.

"Now it's my turn to suck on something."

With that she pushed me off of her and I rolled onto my back. She got on her hands and knees and started to unbutton my shorts. I helped as best I could and took my shirt off. She soon had my shorts and underwear off.

"God, you have a beautiful cock." She said, "My husbands was average size, but thin."

I was a little embarrassed by this but also liked the complement. She then reached out and started to run her hand up and down the length. God it felt great. She then tried to wrap her finger around it. It took both of her hands to get all the way around me.

But then she started to really pump it up and down. I was in heaven.

I reached down and started playing with her closest breast. Sandy then bent down and ran her tongue over my head. I almost came the feeling was so intense. She put the head in her mouth and started to suck. And although she couldn't get very far down I didn't care. No girl had ever done that to me before.

She continued to pump her hands up and down my shaft while sucking on the head. I was so turned on I couldn't believe it. After about five or six strokes I was ready to cum. I told her as much and she stopped sucking on me and slowed down her stroking of my cock. She then smiled at me and told me she wanted me to cum. She wanted to feel my cock pulse as I shot my cum all over her. As she told me this she increased the pace of her hands on my cock. That was all it took. I let out a groan and started to spurt cum all over her torso. I had three really big jets that covered her beautiful breasts. I remember seeing it cling to her nipples as they swayed and jiggled from her hands continuing to pump me. She then put her mouth back over the head of my cock as I had two smaller convulsions. After, when she looked up at me, she looked so sexy. She had a little bit of my cum dripping out of the corner of her mouth.

I quickly pulled her up to me and we started kissing again. I then moved my head down to her breasts and once again took one of her nipples into my mouth. She let out a low moan as I licked and sucked my cum off her tits. Now it was my turn to get her pants off. I pulled her jeans and underwear off together and couldn't believe my eyes. Her pussy was shaved bald except for a small tuft of hair on the front. I had seen plenty of pussies in magazines before but never one in person. It was so beautiful. Her lips were pink and swollen. And her clit was standing up from its hood. There was a slick glistening from her wetness over everything. And oh the smell was so intoxicating. I had never gone down on a girl before but knew I wanted to. I had read about it in Penthouse Forum and such, and couldn't wait to try. Slowly I knelt down between her legs as she spread them open for me. I put my hands on her thighs and ran them up and down. When I got my hands up to her inner thigh and then ran them back down the pressure caused her pussy lips to open slightly. I moved my head between her legs and reached my tongue out and tasted a pussy for the first time.

It was so sweet. (I still love the taste today and love to give head.) Slowly, I ran my tongue up and down the length of her slit and then up and over her engorged clit. I remember her shuddering when I did that. I then opened my mouth wide and really dove in. I remember snaking my tongue up into her as far as I could, tasting as much of her as I could. Then bringing my tongue up and over her clit. I was trying to remember everything I could from those Forum letters so I would please her. I then closed my mouth over her clit and gently sucked, flicking my tongue over the end of it. I remember Sandy gasping when I did this. Taking this as a good sign I redoubled my efforts. Sandy pushed my head away. Telling me that I was being too rough. I slowed down and then took my time. We went at this for some time, and I was loving it. But then Sandy stopped me.

"Alex, I have to tell you I've never been able to cum that way. I love it but can't quite get there." She said very sweetly. She must have seen the downtrodden look on my face, as I really wanted to please her as much as she had me. "But," she continued, "I'd really love to feel that thick cock of yours in me." She didn't have to ask twice. I'm not sure I had even gotten soft. (Ah, the glory of being 21) But with that statement I was hard as I had ever been. She gently pushed me onto my back and once again straddled me. But this time there was nothing between her beautiful naked pussy and my swollen cock. Slowly she lowered herself down onto me. To this day, I can only describe the feeling as total shock. I couldn't believe anything could feel that good. I lay there unable to move, my brain lost in this haze of ecstasy. Once she had lowered herself all the way down on me she started a slow grinding of her hips. God, the ecstasy was only getting better. At some point I reached up and cupped a breast in my hand, feeling the nipple poke out between my two middle fingers. Slowly our rhythm built and soon we were moving in an ever-increasing spiral to infinity. Her eyes were shut tight as she rode me. Small mew like moans escaping her body. Then all at once, her body went ridge, her eyes few open and locked on mine, a primal scream erupted from her. I lost it at that point, cuming and filling her cunt with more cum then I thought I would ever have in my body. Sandy collapsed on top of me, both of us trying to catch our breath. I remember thinking, "Wow, I'm no longer a virgin." Then I said something really stupid. "So, did you make it?"

Hey, I was still naïve. Sandy just looked at me like I was crazy and burst into laughter, throwing her arms around me.

We actually did get her room painted that weekend, and did it naked to boot. To this day I get an erection when I have to paint something.

As for Sandy and me... Well, I was young and dumb and made the classic mistake of confusing love and lust. I broke my heart over her. But looking back, I realize it was my fault and not hers. She was always very nice to me, even when I didn't deserve it.

A few years ago, I was back in town and drove by her house. I don't know if she still lives there or not, but there was a swing set in the front yard. I like to think she found a great guy, and is happily married with a family now. What I am sure of is that I never could have had a better teacher.

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7 Comments
AnonymousAnonymousabout 8 years ago
Then

Take out then. Too many of them. Great first time story.

AnonymousAnonymousalmost 11 years ago

great story keep writing but please spell check (just a pet peeve of mine) lol

AnonymousAnonymousover 13 years ago
Very romantic, very good storytelling

Grammar and punctuation errors aside, your short story read easy and authentic. It was more than just a story about sex. It is a sweet little story about a boy becoming a man, told with warm authenticity. It reads truthful, almost autobiographical.

I gave you 5-stars because of the content and the feel of authenticity you projected. I liked this story very much, A_N_L. Keep up the good work!

Oh, and for future reference, please break down your paragraphs into four-five lines at the most. Reading online is harder than from a paper page, and smaller paragraphs are most helpful. :-)

AnonymousAnonymousover 15 years ago
big cock

The story was great but I have noticed that most of the men in these stories have either 7"8"or 9" cocks.

I don't think that is the real world. Maybe you have really big cock but most of us don't

h1s4k0h1s4k0over 15 years ago
HOLY SHIT!

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Aside from the few typos and punctuation errors (I can let 'em pass lol) that was amazing!

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Remember me telling you about that other author of mine that I absolutely DIE over every time I read his work?

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Yeah, you rank RIGHT up there with number 1 as well. I rank you on a different level, because this story/your style is MUCH different from him and there's no comparison for genres.

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Your writing is BEAUTIFUL!

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It flows SO well. The story is told so... sequentially (seeming). It's nice. It's not hard to read. It's easy... which is what I will be needing in the next few stories to come with yours, as I will be "not holding back my urge" as you requested if such emotion struck me upon reading your submission - and it has.

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^_~

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