I have written before about one of my fantasies of helping a young man lose his virginity. My neighbor Timmy has only fueled this fantasy by spying on me while I tan. When I would see him watching me I would put on a little show for him by flashing him and seductively rubbing my pussy. My husband Sam was always the beneficiary my little fantasy as it would make me very horny and very wet. I would pretend Sam was Timmy putting his cock into his first pussy. Sam enjoyed playing the part of the inexperienced virgin by being seduced by the horny housewife. He would often tell me that I was being mean to the boy by showing him my goods but not giving him relief. Sam would often tease me that I owed it to Timmy to for all the times I had left him with blue balls, as Sam was sinking his cock deep inside me.
The first time I noticed Timmy watching me, he was only 16 at the time; that made him off limits but that didn’t stop my fantasy. As Timmy turned 17, I thought me might lose interest in watching me, but he kept watching and I kept fantasizing. I started calling him over when I would see him in his yard. Timmy was always anxious to help me with work in the yard or garage and we would talk.
While Timmy helped me we would talk about school and as we got more comfortable I would ask him about girls. Timmy told me that he had a couple of dates but nothing serious. I asked him what base he had gotten to.
Timmy blushed and told me he had gotten to 2nd base, he guessed. He said that he had kissed and rubbed a girl’s chest. He also said the girl backed off when he tried to tongue kiss her and go into her shirt.
“Your not at 2nd base till you have the girl’s shirt and bra off, well is she is wearing a bra,” I said as I noticed that I wasn’t wearing a bra at the time, and my nipples were pointing though my t-shirt.
Most of the time when I’m in the garage or yard I don’t wear a bra, so I began to bend over a lot knowing that Timmy was looking down my shirt at my tits. Now my tits aren’t big but they are perky and Timmy seemed to enjoy looking at them.
I continued to flirt with Timmy over the summer getting more and more forward with him. I would put my hands on his shoulders and brush his legs when we would talk. Timmy would tell him me how comfortable he was talking to me and how much he liked helping me. He said he couldn’t talk to his parents about sex and things like that, but he could with me. Given that, I got even bolder with Timmy, using words like cock and pussies. I even asked him if he jacked off thinking about other women, he told me that did and liked looking at porn.
Timmy surprised me by asking me how I lost my virginity. We sat for 20 minutes as I told him in great detail how I let the first boy fuck me. I could tell Timmy had a raging hard on as I told him my story. He tried to hide it but I called him on it. I told him that it was natural for his cock to get hard when talking about sex, so don’t worry about it.
I think I had embarrassed Timmy by calling attention to his hard on because he didn’t come around for a few weeks but as fall came he started to come by again. He would ask to help me in the garage and the yard. He was telling me that he was still to shy to ask girls out and that I was the only beautiful woman he was comfortable talking to. Our conversations always seemed to have sexual overtones.
One Saturday afternoon Timmy was helping me put away some boxes of yard supplies up on a shelf when I started to loose control of the box I was putting away. I yelled for help as he was picking something else up at the time. Timmy got behind me grabbing the box. As he we both held the box above our heads Timmy’s crotch area was rubbing against my ass. I could feel his hard cock pressed against my cheeks. I pushed my ass back against him feeling his hard dick poke into my ass and told him that we were almost there and to push forward. As I ground my ass against his dick Tim let out a little moan. I told him to hold it right there as I rubbed my ass up and down his crotch. We were essentially dry humping with our hands holding a box on a shelf.
I told him, “That’s good right there,” we both knew I wasn’t talking about the box. I was close to turning around and doing something more when Tim’s mother called out for him.
Tim backed up with his hand covering his crotch and said that he had better go. I thought he had cum in is pants the way he was covering up.
I didn’t have a lot of contact with Timmy during the winter, just not outside enough to see him. As spring came I was back out tanning and so was Timmy back to watching me. I came in from one of my tanning sessions very horny where Timmy had been watching me. I pulled Sam into the bedroom for a good fucking. I told Sam that I was very horny and need his cock in me. Sam was quick to comply and couldn’t help but notice how wet I was. Sam asked if I was fantasizing about a virgin cock in me again. I had to confess I was.
I came hard after a short time with Sam’s cock in me, Sam then shot his load in me. As we were lying on the bed with Sam’s cum draining out of me, Sam suggested that have a couple glasses of wine and invite Timmy over next Saturday. Sam reminded me that he was going to be out of town for the weekend and it would be a good time to fulfill my fantasy if I was brave enough and didn’t chicken out. I took it as a dare; Sam had been noting that I had chickened out before every time I had Timmy over here.
I grabbed Sam’s soft cock and snapped at him that maybe I will call him over and make him a man. Sam laughed and told me that he didn’t think I would, but if I did I would have to call him afterward and tell him the details.
I walked to the bathroom to wipe the Sam’s cum out of me, thinking to myself I will show him whose chicken.
As Sam left that Saturday morning I was getting excited and nervous. I was in my head working hard to talk myself into seducing Timmy. I decided that I would take a nice warm shower shaving my legs close and make sure my pussy was also clean shaven. After my shower I posed in front of the mirror thinking to myself that I hoped my 17 year old neighbor would be excited by my 34 year old body. I rubbed the smooth skin around my fresh shaved pussy and thought “Yeah he will want his cock in here.” I found my skimpiest bikini that just barely covered my pussy and tits. I figured that would be the best way to entice him by showing as much skin as I could.
About 11:30 I went out to the back yard to tan and hoped that I would see Timmy. I lay there for a bit and then heard Timmy in his back yard mowing; I stood up and waved. Timmy stopped his mower and came over to the fence. He apologized for making so much noise while I was tanning and asked me if I wanted him to do it another time. I told thanks but it was okay.
I asked him what he was doing for the day and he told me he had to wash his dad’s car but that was it. I told him that Sam was out of town and asked him if he could give me a hand with some things in the house after got done washing the car. Timmy said that he would and almost ran back to his mower.
I couldn’t help but notice that my nipples were hard and my pussy was beginning to moisten. I went into the house to have a bite to eat and pour a glass of wine. My pussy was showing excitement but I was getting nervous about really going through with fucking a 17 year old. I thought to myself that I could always back out if he got over here and it wasn’t right. My head kept questioning whether it was the right thing to do, but my wet pussy was telling me to go for it.
After my 2nd glass of wine I went to the front door and saw Timmy washing his Dad’s car. I stepped out waiving to him and told him that when ever he was done to come on over. As I went back in the house I thought to myself “Oh shit, I have to have something for him to help me with.” I quickly ran upstairs and pulled some boxes off the top shelf in our bedroom closet. I also put away the dildo that was on the night stand, though I thought that might give him the idea that I wanted to fuck.
Just as I was finishing up the door bell rang. Tim was standing on the porch very anxiously. Before I opened the door I rubbed my nipples though my small bikini to insure they were hard and poking out. As I opened the door his eyes immediately got big as he stared at my body in the very small bikini. I asked him if it bothered him that I was still in my bikini, I told him I could put on a cover up.
He gulped and said no that it was fine.
I modeled a little for him telling him, “I get a really good tan in this one, you like it?”
He said back, “Yeah it’s hot, I mean really nice.”
I told him, “I know what you mean, thanks.” The bulge in his pants told me that my suit was having the desired effect.
We got upstairs and I showed him the boxes I wanted moved. Timmy’s eyes kept going to my hard nipples and then back to my face. I knew it was about time to decide if I was going chicken out like Sam thought or have the nerve to give Timmy his action with a woman. I went back in forth in my head several times till looked down at the tent in his shorts and just thought “fuck it.” I grabbed Timmy giving him a big hug telling him, “Thank you, I want to pay you for helping.”
Timmy said, “You don’t have to pay me, I like helping you.”
I stepped back from Timmy reaching up to the knot in my top saying, “How about I pay you in another way? You’ve been staring at tits since you got here, the least I can do is show them to you; but you have to promise not to tell anyone.” I untied my top and let it fall to the floor.
Timmy just stood there with his mouth open staring at my tits. I had gone so far there was no going back now. “Do you want to touch them?” I said as I reached for Timmy’s hands and pulled them to my tits. Timmy started rubbing and squeezing my tits. I asked him if he liked my tits, but before he could answer I reached down and grabbed the tent in his pants. “This hard thing tells me you do.”
Tim let out a groan as I squeezed his cock. I pulled Timmy’s shirt off and told him that I really liked to have my nipples kissed. He leaned down without a word and started kissing and sucking on my tits. Now I was the one moaning. Timmy kissed my tits while I squeezed his cock in his pants.
I pulled Timmy’s head up from my tits and whispered in his ear that I thought his cock needed some attention, “You think your cock needs a kiss?”
Timmy grunted a “Yeah” But nothing else.
I moved down to his shorts, pulling them down. His dick sprung free as his shorts as underwear hit the floor. I looked up into his wide eyes as I grabbed his cock putting my lips around the head of his dick. Timmy moaned loudly as I took his cock into my mouth. I licked up and down his shaft like it was an ice cream cone then sucked on the head of his cock.
Timmy was really getting into it saying, “Oh god, I can’t believe this.” He kept saying that several times.
His six inches was smaller than Sam’s, so I was able to take most of it into my mouth without much trouble. Timmy responded to my sucking by beginning to pump his cock into my mouth. I was afraid he was about to cum so I stopped sucking him and stood up. I moved my crotch against his and asked him if he was ready not to be a virgin any more.
Timmy’s eyes got wide again and all he could say was, “Really, you mean have sex?”
I grabbed his cock and put my lips to his ear and said, “Yes Timmy, you are going slide your cock in me and we are going to fuck.” I slipped my bikini bottoms off and ran my finger though my very wet pussy. I put my finger up to Timmy’s lips to give him a taste of my juice. “Remember you can never talk about what we are doing,” I said to him as he tasted my finger.
I moved over to the bed getting on my back spreading my legs wide. I rubbed my pussy lips that were glistening from my juice. I motioned Timmy to come on in.
Timmy just stood there staring at my pussy saying that he had never done this and wasn’t sure what to do.
“Timmy I know you’re a virgin, just come down her and put your dick in my pussy, it will know what to do.”
Timmy crawled over me staring at my bald pussy. I pulled his face to mine and kissing him. I plunged my tongue into his mouth meeting his tongue. I pulled back laying my head on the pillow.
“Ready?” I asked him.
Timmy just shook his head as I guided his cock down to my pussy lips. I told him “just go slow and once you’re inside me just pause for a moment before you start fucking me.” Once his cock head was inside my pussy lips I pulled my hand away from his dick and looked him in the eye telling him, “Okay now slowly push it in.” My pussy was so wet with excitement as Timmy’s cock slid right in.
“Oh God that feels great, can I start fucking you now?” Timmy said.
“You’re fucking me now Timmy, but yes start sliding you cock in and out of my pussy, doesn’t that feel great?” I told Timmy as he started to pump his dick into me.
“Oh yeah, thank you so much. This is the best feeling ever.” Timmy pumped a few more times then let out a loud grunt.
I knew instantly that Timmy had just cum inside me. He started apologizing, “I’m sorry, I just came in you, I’m so sorry and I’m not wearing a condom.”
“It’s okay Timmy, just keep your dick in me, I’m on the pill so there is no need to worry. I like the feel of a cock and cum inside me,” I told him. “How does it feel not to be a virgin any more?”
“It was great I just wish I could have lasted longer,” he said
I told him, “You will next time.”
“Next time?” Timmy asked.
“Just keep your dick in me and your cock will be hard and ready to fuck again in no time,” I told Timmy as I gave him a nice wet kiss.
After a few minutes of laying there with Timmy’s soft dick in me, I started to squeeze my pussy around him and move my hips a little. Timmy’s cock started to respond and harden. Timmy moaned as his cock came back to life. I pulled my mouth to Timmy’s ear biting on his earlobe I said, “Are you ready fuck me again?”
Timmy just said, “Oh yeah,” as he started to pump his cock into me again.
After a short time of pumping I told Timmy to stop. He looked at with a puzzled look, like he had done something wrong. I told him to roll over I was going to get on top. He quickly did as he was told, moving to his back with his hard cock wet with a mix of his cum and my juice. I got up and grabbed some tissue quickly wiping up some his 1 st load of cum that was dripping out of my pussy. I moved over top of Timmy lining my pussy up with his cock. I eased myself down on him this time with me letting out a moan. I told Timmy he would last longer if I controlled the speed of our fucking. I pulled Timmy’s hands up to my tits and told him that this was the good thing about this position he could play with my tits while we fucked. I reminded him that I also liked my nipples kissed. Timmy was quick to comply, leaning up kissing and licking each of my nipples.
Timmy looked up at me and asked if he could kiss me again, he said he really liked what I did with my tongue in his mouth. We kissed for a while exchanging tongues in each other’s mouths with Timmy’s hands still fondling my tits. Timmy’s breathing increased as he was pushing his cock up into to me harder and harder.
He said, “I’m going to cum again.”
I grabbed him hard and bit his ear whispering to him, “Cum hard and shoot your load deep into me.”
Again Timmy complied, he grunted and came a 2nd time into my pussy. I rode him till I was sure he was done and then rolled off his dick.
I reminded Timmy that he could never tell anyone that we fucked. I told him that if he ever said a word Sam would kill him. I knew that he was somewhat afraid of Sam.
“Oh shit, are you going to tell Sam I fucked you?”
I told him that it was okay, “Sam will be okay with it as long as you keep your mouth shut.” As Timmy and I were talking, I was playing with the cum that was oozing out of my pussy. Timmy could take his eyes off my pussy and his cock was beginning to stir again. I thought about fucking him a third time, but I figured that two times was enough for Timmy’s virgin fuck. I told Timmy that he should get dressed and head home.
Timmy got dressed and thanked me again and shyly asked if he could come over again and help me with things.
I got up and patted his crotch and told him that before he would get to fuck me again he would have to earn it.
He said, “Sure whatever you want me to do.”
I gave him a kiss on the cheek and said, “Next time I’m going to show you how to eat my pussy and you better make me cum.”
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