Infatuated with an Older Woman

Ever since I first became attracted to girls I have had a huge crush on my best friend Ray's mom. When we were younger she was always the most beautiful woman I had ever seen and she still is. Whenever I would go over to Ray's house to hang out by the pool Jackie, which is what she insisted we all call her, would come out wearing a bikini and I would always get a hard on just looking at her sexy body. As soon as I would get home I would have to rush to my room and jack off while I fantasized about Jackie, which is what she insisted I call her. She always said when someone called her Mrs. Anderson it made her feel so old.

As I got older and started dating I noticed I would always be attracted to girls and now women that reminded me of Jackie. They would have to have blonde hair, big tits and a gorgeous ass just like Jackie and when I make love to them, most of the time I would fantasize that I was making love to Jackie. Then last month it finally happened and it was even better than I had always imagined. Since that first night together we have made love almost every night and it just gets better and hotter.

It all started the night before Ray's wedding after the rehearsal dinner. I was going to be his best man so I sat at the table with him, his fiance Kelly, Jackie, Kelly's matron of honor and Kelly's parents. That night Jackie had on a short dress which showed off her long sexy legs and it also showed plenty of her generous cleavage. I could barely take my eyes off her all night during dinner and then afterwards I went to my favorite bar to have a few drinks and find someone that reminded me of Jackie to take home and have sex with. But as it turned out I didn't have to find someone that reminded me of her because I got the real thing and it was amazing.

I'd only been there long enough to have one drink and hadn't even started scoping out the women yet. All of a sudden I heard a familiar voice ask me if the stool next to me was taken. At first I thought I was imagining things but when I turned around there was Jackie looking hotter than ever. I jokingly said that I was saving it for her and she said "you seem always know the right thing to say Jimmie and you're so sweet."

As she climbed up on the stool I glanced down and her short dress rode up exposing even more of her sexy legs and I could already feel myself starting to get a hard on. When the bartender came over and asked her what she wanted to drink I told him to put her drink on my tab. Jackie said that wasn't necessary saying she could afford to buy her own drinks and I told her I knew she could but I wanted to and she thanked me.

After he brought her drink I said "I've never seen you in here before Jackie, what made you come in here tonight?" She said that she had heard me and Ray talking about the bar before and wanted to see what it was like. She then added "now that I'm here it just makes me feel old." I told her she shouldn't feel like that because she was by far the most beautiful woman in the place. She touched my arm and said "you are so sweet Jimmie, I'm surprised some beautiful young woman hasn't scooped you up." She left her hand on my arm for a few more seconds and just her touching my arm I could feel my dick getting even harder.

We had a couple more drinks before she said she needed to get an Uber and go home because she had a lot to do before the wedding. I told her I could give her a ride home and she said "I'm sure you came in here tonight looking for a young woman to have some fun with" and I stopped her by telling her I didn't mind at all. I could see a sexy grin appear on her beautiful face and for the first time I wondered if I might actually have a chance with her.

After I paid for our drinks we went out to my car and I opened the door for her and she said "not only are you the sweetest young man you're also a gentleman, one day you're going to make some young woman a very happy woman." As she sat down in my car her dress rode up even higher and I could see her sexy red panties. When I got in the driver's side I glanced down to see she hadn't pulled her dress back down and rode the entire ride to her house with her sexy panties exposed and I thought I was going to cum in my jeans.

When we got to her house I walked around to open the door for her again and as she swung her legs out she gave me a great view of the crotch of her sexy red panties. i walked her to the front door and she asked if I'd like to come in for one more drink and I told her I would love to.

After she made us both a drink she said she wanted to go put on something more comfortable and she would be right back. when she came back into the living room my jaw dropped, she had on a short silk night shirt and she said "now that feels so much more comfortable. I could see her hard nipples poking through the silk material and I got an instant hard on and I was scared she might see it so I placed my hand over it. She then said "I hope you don't mind me wearing this Jimmie I just hate wearing a dress."

I told her that it was her house and she could wear whatever she wanted and she said again how sweet I was. I thought to myself "if she only knew how much I would love to see her without that night shirt on she wouldn't think I was so sweet.

After we finished our drinks she asked me if I'd like one more and I told her I better not considering I had to drive home. What she said next took me completely by surprise, she said "you could always just spend the night and maybe we can get to know each other much better." She then got up and went to make us another drink and when she came back in the living room she sat even closer to me than before and our legs touched.

She thanked me again for giving her a ride home and I told her it wasn't a problem at all in fact I kind of enjoyed her company. She then said she hadn't been completely honest with me and I asked her what she was talking about. She said "I saw the way you were looking at me at the restaurant during the rehearsal dinner and then again at the bar and quite frankly it turned me on having such a handsome young man look at me that way.

I decided to lay all my cards on the table and told her she was the most beautiful woman I had ever seen and I had been fantasizing about her since I was a teenager. She reminded me of our age difference and I told her I didn't care about that and I had never wanted anyone as much as I did her at that very moment.

The next thing I knew we had sat our drinks on the table and we were making out like a couple of horny teenagers. When I moved my hand up to fondle her firm breast through her silk night shirt we both moaned into each other's mouth. After a long passionate kiss she pulled back and said "I can't remember the last time I was this turned on Jimmie are you absolutely positive about what we are about to do?" and I told her I was. She "we would be much more comfortable in my bedroom, would you like to go there before we go any further?" I told her I didn't care where we were as long as I could finally live out my biggest fantasy.

Jackie stood up and held out her hand for me and led me to her bedroom where she pushed me down on the bed and started to unbutton my shirt. After she had it off she moved her hands down and unbuttoned my jeans and since I never wear any underwear as soon as she pulled my jeans far enough down my hard cock sprang free. She began to move her hand up and down on my cock saying "you're so hard Jimmie, would you mind if I gave you a blow job first?" and I told her I would love that.

She kissed me again before she started to kiss her way down my stomach until I could feel her hot breath on my cock. The next thing I felt was her soft tongue licking up the pre-cum that had leaked from the tip. She then ran her tongue down my shaft to my shaven balls and sucked them for a second before licking her way back up to the head. I watched as she looked up at me and opened her mouth and slowly sucked my entire length inside her warm mouth.

As she began to move her talented mouth up and down on my cock it wasn't long before I could feel the cum rising up from my balls and I moaned if she didn't stop she was going to make me cum. That only seemed to make her suck harder and within a minute I was telling her I couldn't hold back any longer. Jackie took my cock down her throat just as I moaned I was cumming and came more than I think I ever had and she swallowed every bit of my cum.

When I finally stopped cumming and she pulled me out of her mouth she looked back up at me and said "I can't remember the last time I felt a man cum like that and I can't wait to feel you cum inside me but first I want you to make me good and wet with your mouth. She moved back up and kissed me as I rolled us over so I was now on top of her looking down at her beautiful face and said "Jackie you don't know how many times I have fantasized about this very moment." She kissed me again before she said "you won't have to ever fantasize about it ever again because you can have the real thing any time you want.

I pulled her night shirt off to see she was completely naked underneath and she looked sexier than ever before. Her big beautiful breast had the hardest pink nipples I had ever seen and I moved my mouth down to suck both of them. Jackie was soon pushing my head down saying "I need you to make me cum Jimmie" and when I ran my tongue over her smooth wet lips for the first time I fell in love with her sweet juicy cunt. I started out by running my tongue over her smooth wet lips before pushing my tongue inside her to get a better taste. I moved my tongue in and out of her s few times before moving it up and started flicking her swollen clit.

I then sucked her clit into my mouth and continued to flick it with my tongue and a second later she was crying out "oh baby you're making me cum, you're making me cum so hard." As I began to feel her warm juices covering my mouth I covered her pussy with it so I could drink every last drop of her sweet cum. Her first orgasm seemed to last a long time and when her body began to quit shaking she said "come up here Jimmie, I need to feel your hard cock deep inside me."

I definitely didn't want to disappoint her so I moved up and we kissed again as she moved her hand between us to help guide me inside her tight pussy. I slowly pushed forward until I had my full length buried deep inside her tight juicy cunt and I began to move it in and out as she moaned how much she loved my hard cock inside her. She was soon moaning she could feel herself getting ready to cum again and I could feel her pussy getting even wetter.

After her second orgasm began to subside she told me she wanted me to do her from behind. I pulled out and she rolled over lifting her gorgeous ass in the air. I moved behind her and started to rub my cock on her wet lips before pushing it back inside her. I grabbed her by the hips and started slamming my cock as deep as I could inside her and she was moaning for me to fuck her harder. I knew she was rubbing her clit because I could feel her fingers touching my cock as it moved in and out of her. I could also feel her tight pussy starting to contract around my cock and she was moaning she could feel herself getting ready to have another strong orgasm and she wanted me to cum with her. A few seconds later I moaned I could feel myself getting ready to cum again and she said "cum for me Jimmie I want to feel your hot cum shooting deep inside my hungry pussy."

I managed to hold back a few more seconds before slamming my cock deep inside her moaning I was cumming in her tight pussy. As I shot another huge load she cried out "I can feel it Jimmie I can feel you cumming inside me baby and I'm cumming with you."

After I stopped cumming again I collapsed on the bed telling her I had never been with a woman like her and I hoped we could do it again real soon. She rolled over on her side and kissed me before saying "is right now too soon?" I told her I didn't even know if I could get it up again she said to let her take care of that for me. She moved back down and started sucking my flaccid member and in a matter of seconds I could feel myself getting another hard on. She continued to suck my cock until she had me completely hard and then moved on top of me and slowly eased her pussy down on my cock until she was completely impaled on my hard cock.

As she began to grind her pussy on my cock I reached up to fondle her big beautiful breast and pinch her hard pink nipples. We were both moaning as she continued to ride my cock until we were both cumming together again.

After that we laid in each other's arms until we both fell asleep and the next morning I woke up to her talented mouth moving up and down on my morning hard on. When she realized I was awake she moved back on top of me and rode my cock until we cumming together again. We took a shower together before I had to go get ready for the wedding but before I left she made me promise I would come home with her after the reception so we could do it all over again and that was a promise I definitely intended on keeping.

That first weekend together was almost six months ago and we have made love almost every night since. At first we tried to keep it a secret but about a month after the wedding Ray came over to her house and caught us together and to my surprise he was okay with it. That night Jackie asked me to move in with her and I did and now we don't care who knows about us.