(Note: All characters in this story are 18 years of age or older.)
In my senior year of high school, Reese Witherspoon was my girlfriend. Now I know you think I am bragging and making this up, but wait until you read about how it all unfolded,, the story of our romance together which took place around thirty years ago...
Reese had always been popular among us guys in high school due to her stunning and gorgeous appearance. Many tried to become her boyfriend but no one succeeded, it was as if there was an invisible wall around her that none of us could penetrate. She was a straight A student, focused a lot on her academic work, and a nerd when it came to reading, a true bookworm, definitely not the kind of party girl you might think of given her pretty looks. She was usually dressed casually with jeans and T-shirt, but at times also wore nice dresses and sexy shoes, just to mix it up... One feature I particularly liked about her were her cute little sexy size 6 feet with their long toes, but unfortunately one could only see them when she wore sandals which was rarely the case...
In our final year we attended an after-hours acting class together, of course, she was stellar there as she already had experience in acting then outside of school. It came to be that the two of us were selected to play a couple that went through some tough times mid-life, with strains on their relationship, teen kids, job challenges etc. A lot of opportunities to express emotions and to interact with each other in a very personal way.
I not only liked Reese's acting and how pretty she looked, but also her kind and friendly character and sense of humor. She just made me laugh a lot while we were rehearsing scenes, for instance, when something went awfully wrong or was just done in a way that appeared off or odd...
A few weeks into the class, I finally mustered the courage to ask her if she would hang out with me some time... I knew about the many failures of other boys to get her attention and to even get a single date, so my hopes were fairly low...
To my surprise, though, Reese accepted, and said "Sure, that should be fun...!" Maybe she had found a liking with me, too? I was hopeful...
A few days later we went out for a walk and some ice-cream and had a very nice conversation... it felt comfortable and warm to be with her and I was in hope that we could have more hang-outs with each other... Reese was indeed game it turned out, and so we enjoyed many walks, dinners, bike rides, visits to a local amusement part, movies and other leisure activities together...
It was really great dating Reese, and for sure she felt the same, the only thing was... she set restrictions on our physical contact... it was okay to hug and kiss each other on the cheek, but she would not have any more than that, she made this unmistakably clear... So, was she my girlfriend, or "just a friend"..." Hard to say at this point if nothing would shift in the physical space between us...
An opportunity did come about a few weeks later, after we had experienced a great evening in the local amusement park with rides, watching marching bands, eating fries and cotton candy and all that... Her parents were out of town that night and we went to her house and hung out on the couch in front of the TV...
We cuddled, and I gave her a few kisses on the cheek, some time later also kisses on her mouth... This was a test, would she say no and tell me to stop...? Nothing! She must like it, I thought, and some time later went bolder and slightly stuck my tongue between her lips as I kissed her on the mouth a second time... Again, nothing! I was so excited that we could cross the wall of intimacy she had built around herself and slowly kept probing her mouth with my tongue...
There, her tongue started to move, as well, and we engaged in a slow, but very sensuous dance of our tongues, playing with one another, pushing in firmly at times, then softly again... All that French kissing had made us quite hot and Reese took her sweater off, exposing her silky white 34B bra to my view...
I could not resist the temptation and my hands started to explore her boobs through the fabric of the smooth bra, while we were still engaged in our super-long French kiss...
Reese broke the kiss to take my sweater off, and then my pants and socks, so I just wore my boxershorts at this point...
Her hands gently traced down my body from my head over my neck, shoulders, chest, tummy, until they reached my boner which had been hard for quite some time...
"I hope this is okay?" Reese asked.
"Of course, that feels really good," I replied.
And with that, she started to gently massage my rock hard cock through the fabric of my boxers...
Now it was my turn and I took off her jeans and socks, as well, leaving her white bikini panties on display... My hands also stroked her body all over from head to toes, and then focused on her sex, I gently rubbed her outer lips through the fabric of her soft panties but purposefully did not want to get further and more intimate at this point...
Then I had an idea... as I had now seen and even briefly touched her feet, this was the opportunity to get more... I raised myself up and asked Reese if she would be ok receiving a foot massage from me... She looked a bit surprised since everything had gone a different direction so far, but was not opposed...
She moved her legs up and placed her feet on my lap... there they were, her perfect cute little sexy feet, right here for me to explore, I thought... her toes were indeed quite long, another cute aspect of her feet I really liked, and in fact her second toes were even longer than her big toes, quite amazing...
I started to provide Reese with a sensuous foot massage, paying attention to her ankles, tops, heels and soles, and varying between gentler and firmer pressure, longer and shorter strokes and rubs... finally I got to her toes and paid attention to each of them individually in a playful way...
"That feels soooo good," Reese purred. "Do you want to... lick them, too?"
No need for this invitation, I had already started to pick her feet up to raise them all the way to my face... their soles were so soft and smooth and had a very delicate flowery scent, maybe from a foot lotion that she had applied... I started to lick Reese's small pretty feet all over, exploring particularly her soles and all individual toes with my tongue, until it was time to suck on her toes... I could put almost half of her foot in my mouth as they were so small, and had the wonderful experience of sucking on them intensely with both gentleness and firmness...
Reese had started to moan subduedly, and when I inserted first one, then her other foot into my mouth, she started to breathe more rapidly and clearly got aroused more strongly, I also noticed a wet spot on her white panties...
Reese then took her feet back down on my lap and started to massage my still rock hard cock through the fabric of my boxers... Experiencing her feet there, moving up and down my shaft and caressing its tip with her pretty long toes felt like heaven to me... I was so relaxed and at the same time so highly sexually aroused that I almost came...
But Reese had another idea,... she took her feet off my boner and lay down on top of me so that our sex touched through the fabric of her panties and my boxers... I started massaging her cute little firm breasts again through the fabric of the silky white bra, and she rubbed her sex against my hard-on, back and forth, back-and-forth... it was not long thereafter that she came first, exhaling loudly, shaking from her orgasm, and creating a big wet spot on her panties... This brought me over the edge, as well, and my cock exploded in multiple loads of cum...
We embraced each other for a long time and then started to French kiss again... what a memorable night where certain boundaries were crossed and hopes for even more were kindled...
Around two weeks passed and the long-awaited prom night of our high school class was finally going to happen... Everyone was jealous of me having Reese Witherspoon as my prom date and she did not disappoint, looking absolutely stunning and gorgeous in her prom outfit, consisting of a shoulders-free red minidress, shiny smooth black pantyhose, and red leather heels... I could not take my eyes off Reese when I saw her in this outfit for the first time, and spent as much time as possible with her during the prom night, we danced many hours together and I made sure to be able to touch her pantyhose-encased gorgeous legs every once in a while when a situation arose...
Reese definitely noticed the attention I gave to her sexy hosiery and when we sat together at a table would tease me without end, for instance, by dangling her red heels from her nylon-clad cute little feet, or by rubbing her feet against my legs, in rare cases going all the way to my rock hard boner, making sure that no one else could see her teasing moves, though...
As the evening progressed and we had become a bit tipsy from the drinks that were available to us despite being under drinking age, there was more cuddling and kissing between us, and we both dreamed about a sequel of a night together once the prom had ended...
While I resented my parents being away for a long planned trip to Europe, I did like the fact that their house was available to use that night without any disturbances and we would have it just for ourselves...
After a few snacks and non-alcoholic drinks in the kitchen, I took Reese by the hand and guided her to my bedroom which she had hardly seen before because we usually would hang out in my parent's living room to watch TV...
Since the intimate adventures two weeks ago where we made out on the couch in her parents' place we had not had any sexual experiences (of course except for French kissing), there just had not been a good opportunity for that in the meantime... I was hoping that this would change in this post-prom night when we had already done so much teasing, kissing and cuddling to get closer to one another...