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Alexandria’s First Time

Alexandria’s First Time

If you recall, we shared with you about the pool party our four couple group threw for our young teenaged babysitters (see The Young Babysitters).

At the time our babysitter, Alexandria (Alex for short) was only 15. She was a cute girl with shoulder length brown hair and brown eyes. She was just starting to develop her womanly figure with a narrow waist and slightly wider hips. I’ll be generous and say at the time she may have been wearing a b-cup, but they fit her well and she wore tops that help accentuate what she had.

We had intended to keep the party decent because of the 4 young girls, but before the night was over we were all naked and engaged in oral sex. The girls watched us 8 adults have sex, but we drew the line with the girls because of their age.

Three weeks after the party, Alex turned 16. She babysat for us 2 days after her birthday and we had a couple of gifts wrapped up for her. She excitedly tore through the wrapping paper and was thrilled with the clothes that Babs had picked out for her. Babs asked if she had a good birthday and she said she had, except there was one gift that she had really hoped for had not received. When Babs asked her what it was, she said that she really wanted me to be her first sex partner and to take her virginity.

Babs and I were both speechless. I just stood there with a blank look on my face and had no idea what to say or do. Babs was pretty much in the same state of shock as I was. Alex could tell that she completely surprised us and started giggling. She told us that was what she wanted and asked us to just think about it tonight as we headed out to our group orgy.

In the car, Babs and I talked about it and neither of us were sure what to do. She was still u******e and I could go to jail and ruin my career if anyone found out, but she was such a cute girl that was maturing into a lovely young woman. I said we needed to think this through very carefully.

We had a great time with our friends. We played a couple sex games and had a few drinks. By the time we all left, we all had sex with each other’s spouse at least once.

On the way home, Babs asked if I had given any more thought to what Alex had said and I told her yes, I had been thinking about it all night. I told her that we really needed to talk to her about this before we decided to do anything. Babs asked me if it wasn’t a crime what would I want to do and I smiled at her and said that should be obvious. She told me that she fully supported whatever decision I made and then said she also knew that I really wanted to take Alex’s virginity.

Just talking about it got me hard again, even after all of the previous activity of the night. We only had a fifteen minute drive and I told Babs that I needed to stop talking about it so my erection would go down before we got home. She laughed and said okay.

When we arrived home, we saw Alex on the sofa watching TV. She jumped, ran over to us, leapt into my arms wrapping her legs around my waist and her arms around my neck and planted a passionate kiss on my lips. Babs chuckled and said that Alex must have been thinking about it all night also.

It took Alex a couple of minutes to come up for air and loosen her embrace. She asked if we, mostly meaning me, had thought about what she had said and I told we had and that we needed to talk and we could talk in the car when I took her home. Alex smiled and said no need to take her home as she told her parents that we were going to be real late and that she was going to sl**p in the guest room next to the baby’s room. Since it was a Friday night, they readily gave their permission. Babs chuckled again and said if only they knew that they were throwing their daughter into the lion’s den. Alex looked at me and said that it may be the other way around.

I peeled her off of me and said that we were going to talk this through before any decision is made, but I needed a drink first. Alex asked if she could have a drink and I told her there was soda in the fridge and she sneered at me and said that’s not what she meant. Babs gave me that look telling me that she needed a drink also, so I fixed us some drinks. Not much to fix for mine as I like Jack Daniels Black label chilled and straight, no ice and no mixer. It’s the best sipping whiskey in the world. Babs noticed that I poured myself a double portion and smiled.

We sat down and I made Alex sit in the chair across from Babs and me. I told her that she was still u******e and that I could go to jail if anyone found out that we had sex with her. She said she understood and that she would not tell a soul. Babs asked her what about all her friends at school, knowing how girls talk and gossip. Alex swore up and down that she would never tell her friends and then told us how much she really wanted me to be her first, especially since the pool party when she stroked and sucked on my cock and watched Babs and I have sex.

Babs asked her what if she accidentally let it slip and others found out and told and got me into trouble. It would cost us my job, career, our house and probably send me to jail. That’s an awful lot to risk. She said she understood and promised over and over not to tell anyone. Then she used logic on Babs, telling her that she trust her with our baby, why not her husband. Babs looked at me and said that was a good point.

Then I saw a side of Babs that I had never seen. She looked straight at Alex and told her that if we agreed to go through with this and anyone found out and got me in trouble that she would surely take revenge on Alex’s f****y in ways that Alex would regret for the rest of her life. Alex’s eyes got big and her expression went blank as probably did mine. Alex quietly whispered, asking what Babs meant. Babs told her that she should just hope that she never finds out what she meant. I noticed that Babs was not smiling and had the sternest look on her face I had ever seen. I’ve seen her mad and this far surpassed that.

Alex stood up, walked over and knelt in front of Babs and told her that she promised she would never say anything and that she would make sure that it never slipped out. Babs told her to go and check on the baby and let us talk about it.

Babs told me that she was satisfied and I asked her what in the world would she do Alex’s f****y. She told me she had no idea but that she just wanted to the put the fear of Babs in her and scare her to see just how serious she was. I told her that she put the fear of Babs in me too. Then Babs again told me that she knew I wanted to take Alex and that she thought it would be okay. I said if she was sure and she said and kissed me and then went to check on the baby and fetch Alex.

A couple minutes later, they returned. Babs told Alex to remember what she said about this ever getting out to anyone and again Alex swore she would keep it just between us. Then Babs told Alex let me undress her and then she was to undress me. The rest would be left up to me.

Alex stood before me in her t-shirt and shorts. I didn’t need to stand up since I was so much taller than her, so I reached out and lifter her shirt over her head and tossed it to the side. Then I unzipped her shorts and slid them down her legs and tossed them over with her top. I sat back and just looked at her, taking in the sight like a hungry wolf sizing up his prey before he was about to devour it. I told her to slowly turn around and more than my mouth was watering as I took in the young beauty before me.

I told Alex to step a bit closer and then told her to turn her back to me. I unclasped her bra and allowed my hands to slide around her sides and cup her tits as her bra fell to the floor. As I held her tits in my hands, she leaned back into me as if totally surrendering to my touch. After a few moments of holding her tits, my hands caressed their way down her sides to her panties. I slipped my thumbs under her waistband and slowly worked her panties down over her luscious little ass. I let her panties fall the rest of way down and I cupped her ass cheeks like I had cupped her tits. Her cheeks were perfect globes of flesh that were soft and yet firm with some muscle tone.

I leaned forward and kissed both cheeks and then licked up her crack and she started moaning. Then I asked her to turn and face me. I watched as her body pivoted, revealing her young womanhood to me once again as she had done that day in the pool. She was definitely a sight to behold and my very erect cock was just begging to be turned loose on her.

Without any instructions, Alex began unbuttoning my shirt and took it off my shoulders and tossed it over onto her clothes. She lifted my undershirt off and leaned down and kissed my nipples. Alex then looked at my pants and told me to stand up and I did. She fumbled trying to get my belt, button and zipper undone and I could tell that she probably had little if any experience of undressing any male before. She awkwardly worked my slacks down and had me step out of them. Just as awkwardly, she grabbed the waistband of my briefs and worked them down.

When she had them down far enough, my hard cock sprang loose and hit her in the cheek. It startled her at first and then she just stared at it and smiled. She worked my briefs down and off and there I was standing naked before a very naked 16 year old beauty who was begging me to make her a woman.

Alex looked at my cock and then up to me with a questioning look and I told her to feel free to touch, stroke, kiss, suck or whatever she wanted. She eagerly wrapped her small hands around my shaft and just held for a few moments without moving. Her touch felt heavenly and I could feel my cock jump for joy. Alex felt it too and looked up at me and smiled. I told her that it was his way of saying he liked her and she giggled.

Kneeling in front of me, Alex said she wanted to taste it again before we had sex and began to kiss and lick up and down my shaft. After swirling her tongue around the head of my cock for a bit, she began working it into her mouth. I watched in awe as first the head and then more of my cock disappeared between her young lips. Several of the other wives had sucked my cock earlier that night, but none of them felt like this little angel did. Without realizing it I started moving my hips, fucking the sweet mouth wrapped around my cock. I wanted to cum right then, but knew I needed to save it for later.

Babs could tell by the look on my face that I was getting close and suggested we stop and allow me to return the favor. I set Alex down on the edge of the sofa and she spread her legs, revealing her delicious little virgin pussy to my hungry eyes. I could smell her excitement as I moved in closer, taking in the view until it became too close to focus on. Her fragrance was intoxicating and I followed the scent to its source, and carefully licked at her opening. She was so excited that her sweet nectar was oozing out and like a winter starved hummingbird, my tongue darted in and out of her pussy, drinking in as much of her nectar as I could.

With my tongue darting in and out of her pussy, Alex suddenly and violently had her first orgasm of the night. I felt her pussy spasm around my tongue and the juices flowed into my hungry mouth. She tasted as sweet and innocent as she looked and I enjoyed every drop I could find. Then I moved my lips to her tiny clit and began licking, sucking and nibbling on it. It didn’t take long for Alex to climax again.

I pulled away and asked Babs if she wanted a taste of the sweetest nectar she ever had and she eagerly moved and started licking and sucking on Alex’s pussy. I took that moment to regain a little composure as I was already getting lost in the moment. I positioned myself so that I could cup one of Alex’s tits in one hand and one of Babs tits in the other. I watched as Babs feasted on the young pussy and made Alex cum again.

The poor girl was out of breath and begged us to stop long enough so that she could recover. Her eyes had that orgasmed glazed look to them as if she wasn’t focusing on anyone or anything. While she was recovering, I stripped Babs and sucked on her tits while I played with her pussy. A couple minutes later, Alex seemed to be back with us and said she was ready for more. Babs asked her if she had ever had that many orgasmed in such a short period of time and she said never and that it was the most sexually intense thing she ever experienced. Babs told her the best was yet to cum as she slowly stroked my cock to keep it hard and ready.

Babs told me that I needed to go grab a couple of condoms and Alex said it wasn’t necessary. She had been on the pill for the past year to help regulate her periods so there was no way she would get pregnant. Then Babs asked her what she would do if her mom or doctor found out that she wasn’t a virgin any longer and she said she would tell them she used the handle of a hairbrush to masturbate with like some of her friends have done. Babs looked at me and said that all bases seemed to be covered and I was up to bat. I asked Babs what position would be best for the first time and she suggested that the old missionary position was probably best as I could better control my movements that way and suggested the bed would be more comfortable so we moved upstairs to our bedroom.

Babs led Alex to our bed and positioned her just right for me to move in over her. Babs began to explain to her that it might hurt at first as her hymen tears and Alex said they had studied that in school and she was prepared. I told her to tell me if she needed me to stop of back out at any time if it was too much for her. Babs assured her that after the initial tearing that she will be filled with waves of ecstasy like she’s never felt before. Alex smiled and said she was ready.

I moved in over her, holding myself up with my arms and knees. I looked at her and asked her if she really wanted to go through with this and she said yes, I leaned down and kissed her. Babs felt Alex’s pussy and told me she was plenty moist and then she helped guide my cock to the entrance to virgin territory. She rubbed the head of cock up and down her slit and Alex’s eyes got big, she grinned ear to ear and whispered for me to make her a woman.

Babs gave me a nod and I gently applied enough pressure for the head of my cock to part her lips. Alex kept her eyes focused on mine as I gently rocked the head in and out of her, allowing her to get used to the feel. Still staring at me, Alex whispered for me to take her now so I applied a little more pressure and could my cock slide in a bit more until it met the resistance of her hymen. Alex said she could feel me in her and told me to go ahead and tear her hymen as she wanted to feel me all the way in her.

Our eyes were still locked each other as I pushed a little harder. I saw her grimace and asked if she was okay. With clenched teeth she nodded yes and I pushed yet a little harder. I could feel her tissue resisting me until suddenly it gave way and allowed me to slide a little deeper. Alex had a few tears in her eyes and again I asked her if she was okay. She nodded and said that she was now a woman and wanted to feel me fill her pussy.

I knew she was still tender so I continued to take it easy, working my way a little at a time. Slowly I pulled a little bit out and then pushed a little more in. Her young pussy was tight that I wondered if I would be able to fit it all in her. I’m hung like a horse, but a have a fair sized cock and it was in heaven. As I went deeper and deeper into our babysitter, a few more tears leaked out the sides of her eyes. Before I could say anything she told me she was fine and that she was just so happy that she couldn’t help but cry. Babs told her that she was the same way when she became a woman.

Eventually I worked my whole cock inside her very tight pussy and just held it there. I could feel the tip press against her cervix and my balls rested on her gorgeous little round ass cheeks. After giving her a few moments to get accustomed to me, I began to gently work my way out and back in and set a slow rhythm. The look in her eyes told me that she was lost in the moment and that she was close to having her first cock caused orgasm. Her pussy was already quite tight, but it started getting tighter and made it difficult to keep up my rhythm. Alex’s back arched, her head lifted up and she had an intense grimace on her face as her body shook from head to toe from her orgasm.

It was everything I could do to move at all in her until her orgasm began to subside. As it did subside I once again picked up the pace and began pumping her a little faster and a little harder. It wasn’t but a minute later that she had another orgasm which again shook her entire body. As her pussy clamped around my cock, I lost control and started shooting stream after stream of my hot seed into that young woman beneath me. The thought hit me as I unloaded that mine was the first seed to ever penetrate this lovely girl.

Now the tears were really flowing and her smile couldn’t get any bigger. Her eyes shined and sparked and the last drops of my seed trickled into her pussy. I lowered myself enough to kiss her again. I looked into her eyes and told her that I brought Alex the girl to my bed and now she’s Alex the woman. She wrapped her arms around my neck and pulled down to her and kissed me like she had never kissed me before.

I had used a lot of sexual energy earlier in the evening and shamefully it didn’t take long for my well-worn cock to go soft. I pressed my groin into her, trying to stay inside as long as possible, but eventually it was time to let it fall out and I rolled to the side of her. Babs was on the other side of her, gently fondling the young girl’s tits. Babs asked her how she liked it and she just said ‘wow’ and laid there and smiled.

A few minutes later, Alex asked if we could do it again. Babs warned her that she could get sore after and to take it easy the first time, but Alex said she didn’t care and really wanted to feel me in her again. I told her I needed help getting hard and she quickly moved down and began sucking my cock. She stopped after a moment and said she could taste my cum mixed with her bl**d and juices and it was the most erotic thing she had ever tasted. Babs said she had to find out, but instead of tasting my cock, she positioned Alex so that she could lick her pussy while Alex sucked me hard.

Watching the two ladies and thinking about being back in that tight young pussy again helped me get back into erect readiness. Once I was hard, Alex asked about other positions. Babs told her that two of her favorites were riding on top and doggy style. Alex said that some of the girls at school talked getting fucked doggy style and how much they liked it. I said doggy it is and lifter her up and set her on her hands and knees. I moved in behind her and gently began to penetrate this newly taken pussy for the second time. She was still tight, but not quite as tight as moments earlier.

Once I was in all the way, I gave one final thrust and Alex let out a small yelp. I asked if that hurt and she said no, it just surprised her and felt like I was ready to go all the through her. I held onto the prettiest young ass I had seen in a very long time and began to pump in and out of her. Babs reached under her and played with Alex’s tits and I felt her hand rubbing along Alex’s clit. I just stared at her ass as I slid in and out of her pussy. Babs increased her tempo of rubbing Alex’s little clit and she soon had another orgasm. Her pussy tightened around my cock and I could feel it contracting in wave after wave. It really felt incredible as if her pussy was trying to stroke me into cumming. I continued to pump her and she had another orgasm before I eventually shot my second load into her. I held her ass tight against me as the last drops of seed squirted into her. As I pulled her tight, she pressed her pussy back onto me as far as she could press.

By now my cock was exhausted and quickly deflated. As soon as I popped out, Babs moved behind Alex and began licking my cum and the young girl’s juices. It didn’t take long for Alex to have another orgasm. As she came, my cum and her juices easily flowed out of her. When Babs had her well cleaned, she suggested that we all take a shower as both Alex and I had worked up quite a sweat. Alex asked if she could shower with us and Babs said that’s what she meant.

The three of us moved into the shower and took turns soaping each other down. I rubbed my hands up Alex’s legs, over her pussy, flat tummy, her breasts and arms then back down her back over her ass and down her legs to her ankles. As I was soaping up one side of her Babs was soaping the other side. Then Alex soaped me up making sure to spend extra time on my cock and balls and she also enjoyed soaping Babs tits, ass and pussy.

After the shower, we toweled each other off. Alex kissed us both goodnight and said she would have great dreams and see us in the morning and headed to the door. Babs asked where she was going and she said to the spare room and Babs told her she was sl**ping with us tonight. She joyfully bounced into the bed and snuggled in between Babs and I. We are all pretty tired and drifted off to sl**p.

In the morning, Alex was still sl**ping sound, so Babs and snuck out of bed. Babs went to quiet and change the baby and I headed downstairs to start the coffee and breakfast. About half an hour later, Alex came walking down the stairs, as naked as we were. We noticed she was walking a little funny and when we asked her she said she pretty sore this morning. Babs told her that she needed to walk normal or her mom would notice and want to know what happened. Alex said her mom and dad were working and wouldn’t be home till later.

I asked her if she was ready to go some more. She looked at me and said as much as she enjoyed last night that she was just too sore but really wanted to do it again the next time she babysat for us. I told her that I would look forward to it as long as she kept our secret. She promised again and said this was the most fantastic thing she has ever done and she wouldn’t do anything to ruin it.

Babs handed Alex the baby who immediately tried to nurse on her bare tit. She commented that it felt really good and Babs said that was one of the best things about breastfeeding.

The three of us spent the morning naked, relaxing and talking. After lunch, we got dressed and took Alex home. By then she was walking more normal. She waved as she let herself into the house and then we pulled away and headed home. On the way home Babs asked how was she and I told her she was fantastic. When we got home, Babs teasingly asked if I was ready for some older sloppy pussy and I quickly undressed her and took just inside the doorway.

Updated: October 21, 2016 — 1:10 pm

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