Andrea Goes the Extra Mile

Story Info
When money is tight, Andrea learns how to earn more.
4.3k words
4.49
37.4k
8
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Andrea and I have been friends for almost ten years. We met when she started dating a friend of mine. Andrea was fresh out of high school then and the first thing I noticed were her flawless sized seven and a half feet. Being that we live in Florida, Andrea was always wearing flip flops and showing off her amazing feet. Andrea is a beautiful girl besides just her feet.

She stands about 5'4" tall and weighs about 120 pounds. Andrea has very blonde hair and blue eyes. She has what I consider to be large tits for her small frame, about a solid "C" cup. She has a flat little tummy with a round and very squeezable ass. Obviously being a die-hard foot lover my main focus is on Andrea's feet, but she has such great legs. A nice toned calf that tapers down to her ankle and ending in a deep Achilles tendon and strong, well defined ankles.

I don't remember when Andrea learned about my foot fetish, but while she was dating my friend, I kept my thoughts to myself. While Andrea is extremely sexy, she is volatile in relationships! After she broke up with my friend, he moved away and Andrea and I remained friends. I would of asked her out to make those feet mine, but she loved relationship drama WAY too much for me. I was fine being just friends and friends with foot benefits.

Andrea craves attention from men and therefore once my love for her feet was out in the open, she enjoyed letting me enjoy her feet. She knew very well how crazy she could make me and I think she loved the attention. Thus began what continues to this day, our "secret" friends with foot benefits. I started dating the woman who is now my wife during the period where Andrea and I were developing of secret foot friendship.

Andrea isn't the type to initiate foot contact beyond texting me pictures of her toes when she gets a fresh pedicure. I am surprised by her more submissive attitude towards my love for her feet and while she never starts the foot fun, she never balks either.

This short story would be a novel if I attempted to write down every foot session we've ever had. To give an example of her discretion and somewhat submissive attitude I remember a bunch of us at a bar sitting outside drinking. Andrea was wearing a simple black dress and black heels without pantyhose.

We were at the bar getting drinks and had a quick alone moment. I leaned in and told her how sexy she looked tonight and asked if she had been wearing those heels all day. Andrea smiled and nodded knowing how much I love that. I joked that she was killing me and she knew it.

We sat back down at the table outside. I made sure I sat next to her. While carrying on a conversation I leaned back and my right hand found her left calf. Neither Andrea or I skipped a beat in the conversation and kept our poker faces on. My hand slid down the back of her calf and she knew exactly what to do without me even asking.

As my hand touched her Achilles tendon, Andrea lifted her left foot slowly out of her heel until it was bare. My cock raged as my hand felt the soft skin of her creamy pink sole. It felt so warm and moist. I stroked the ultra soft skin under her toes and pink toe pads. I continued her foot massage and she kept her foot there until I was done.

Over all of these past years Andrea has let me smell, kiss, lick, and suck on every part of her feet. We've had a few sessions where we are alone at the house together and I'll orally rape her feet until my tongue and jaw ache. Andrea has ticklish feet as well and I've pinned them down and tickled her until she is bucking and begging. Which brings me to the limit of our unspoken foot relationship.

I have gotten overwhelmed in the past and placed one or both of her feet on my cock over my shorts. While she won't break the mood and get mad, she will move them away. I've never wanted to ruin what we have so I don't press the issue. She is friend's with my wife and I'm sure has a limit to what is acceptable.

I've been dying for years to fuck her feet and cum all over her soft soles. Again, not wanting to ruin my ability to worship her feet I left the issue alone. That all changed recently. Fast forward to present day and Andrea is a 27 year old single mom. Trying to finish college as well as work full time. Since her "baby daddy" was a dead beat, she has been trying to make it on her own. My wife and I have been supportive and try to help her in any way we can. So Andrea felt comfortable approaching me the other day and asking for money. I could tell it was hard for her to ask and being that my career is going great, I was in a financial position that allowed me to help her.

She and I were sitting on my back porch by the pool when she asked me. Everyone else had gone to the store and we were alone. I had a few beers in my by this point and was feeling it. So when Andrea asked for the money, which was a fairly hefty amount, I joked with her about what she was willing to do for the money. Honestly I was just joking and wouldn't of really made the money conditional. However it was her reaction that aroused me and made me continue down this path.

"You know we are happy to help you Andrea, but what are you going to do for me for that much money?" I said with a funny smirk and a raised brow thinking she'd see I was kidding.

Looking distraught Andrea lowered her voice and said, "Well what do you want me to do?"

It must of been the lowered voice and submissive tone that instantly aroused me. I lowered my stare to her pink toenails. Her head followed mine.

"What? You want my feet?" Andrea questioned with a confused look on her face. I assumed she was confused because I already been enjoying for years for free.

I debated ending the joke, but I liked where this was going and decided to play it out for a while longer. I continued to stare at her dainty feet as I built up the nerve.

"What do you mean you want my feet? Do you want to take more pictures of them or something?" Andrea asked with question in her voice.

"I'll be happy to give you the money Andrea, but I want a night alone with your feet. I want you to give me a foot job." I said bluntly

There was a moment of silence where Andrea pretended to be confused about what exactly I was asking her to to. She knew exactly what I wanted but played dumb as she processed her response. "What do you mean by a foot job?" Andrea asked.

"Well Andrea what I want is a night where your mom keeps your son and you wear heels all day. I'm going to come over and I want you to jerk me off with your feet?" I told her.

She stayed quite for a minute and I saw the look on her face turn from confusion to one of betrayal and somewhat angry. "I'm not some kind of slut." she informed me. "If you don't want to give me the money ...fine, but I'm not going to let you have sex with my feet."

I had backed myself into a corner by playing a joke that went wrong. She was frustrated and at that very moment everyone came home and she got up in a "huff" and acted like nothing had happened. I kept my distance from her during the party and felt guilty. A few hours later Andrea found me alone in the house and walked up to me and simply said, "When?" with a defeated tone. I told her tomorrow night.

I showed up and Andrea opened the door. She was wearing a simple black dress with pink accent. She had on sheer black pantyhose and black heels. To lighten the mood I joked about her wearing pantyhose because this was the first time I ever saw her in them. We laughed and she said something about under the circumstances. That let me know that she had put them on trying to be sexy! She looked so hot that my mind started thinking how she'd look when I was fucking more than just her feet.

We walked over to the sofa and she sat down and let out a nervous sigh. I leaned down and picked up her feet and put them in my lap. She sat back and quietly watched as I slowly removed both heels. I held her feet together and raised them up so I could look at her soles in this sheer black hose. Damn they looked amazing! Sheer enough to see all the lines that crisscrossed her soles.

I leaned in and planted my face into her moist soles. Inhaling deeply and drinking in the wonderful light scent her slightly sweaty feet provided. My lips kissed the parts of her soles that were touching them. I rubbed her feet up and down my face. The erection in my shorts was getting painful and my breath became heavy as my grip on her narrow ankles became tighter.

"Fuck Andrea, you have NO idea what your feet do to me." I groaned quietly. I took both feet and placed them squarely on top of my erection. This time instead of moving them away, she left them there.

"I guess you really DO like my feet." Andrea joked. I felt her feet began to move ever so slightly and I released my tight grip on her ankles. I leaned back and she slowly moved her feet up and down my shaft. "Is this what you want me to do?" Andrea asked with this sly and flirty smile. It felt so good looking at her high arched feet sliding up and down my cock that I couldn't speak for a minute.

"Well, you've got the right idea, but let me do this." I said as moved her feet and pulled my cock free from my shorts. I placed her feet on either side of it and she attempted to do what she thought was jerking me off with her feet. Her movements placed her in an obviously strained and uncomfortable position, but I didn't care. She picked up the pace as her creamy feet tried to hold my cock between her arches.

Andrea was really concentrating on a rhythmic motion with her feet. With a strained look on her face she said, "Are you gonna cum or what?" She was straining her stomach muscles with her knees up and her feet "hovering".

I decided to give Andrea a break. I told her that she could relax for a few minutes and rub her feet on my cock. With her right foot Andrea pushed my cock back so that it was pressed against my chest. The ball of that foot slid slowly up and down my shaft. I reached down and took ahold of her left foot and pulled her leg out straight. I used my free hand to somewhat massage her left foot but more so to feel the texture of her foot encased in the nylon material. I stared at her left foot and allowed my fingertips to trace every line and wrinkle in her sole.

My heart rate and breathing increased as Andrea was applying just the right amount of pressure to my cock on all the right areas. She could see my chest heaving and feeling the slight arch in my back as I thrust my cock against her sole for added pressure. I knew she must feel degraded to a certain degree by having to become a foot whore, albeit a temporary one. However the way she was moving that foot up and down my shaft made me wonder if she wasn't at least somewhat turned on.

Being a die-hard sole lover, I really wanted to cum on Andrea's soles. If I were to cum in our current position, I could cum all over my own chest or perhaps straight up into the air turning Andrea's sofa into a cum geyser! Even then, my cum would reenter the atmosphere and land on top of Andrea's indentured feet. I wanted her laying face down so that I could fuck her feet.

"Let's go upstairs to your room." I said with a very matter of fact tone.

Andrea took a look of confusion and mild frustration. "Are you gonna cum or what? Am I doing something wrong?"

We had only been at it for about ten minutes. The emotion in Andrea's question seemed to be mixed with the feeling of wanting this to be over but more than that her inherent need to be able to make a man cum. "Don't worry baby, you are doing just fine." I said as I removed her feet from my lap. I reached down and picked up the heels she had been wearing and told her to lead the way.

The staircase leading to the second floor of Andrea's apartment is long. I stayed a few steps down from her and watched as she slowly swung her fine ass back and forth. I had seen Andrea walking plenty of times and it wasn't her normal walk. She knew my eyes were fixed on her ass and she made sure to switch it back and forth like a good girl should.

Once in her room she paused and looked at me as if to say, "Where do you want me?" I set her high heels on the foot of her bed and took her by the hand. Guiding her to the foot of the bed. Once there I turned her around so that she was facing the bed with the front of her thighs up against the mattress. I positioned myself behind her and took her long blonde hair in my hands and removed it from her shoulders and laid it down the middle of her back. I snuggled in close and rested my cock against her ass and began to massage her shoulders.

She stood there with a somewhat rigid posture. That is until I leaned forward and began kissing the back of her neck. As I softly kissed her neck mixed with gentle licks using the tip of my tongue, I felt her relax. I heard her breath heavier and I pressed my cock harder against her ass. I reached up and took her hair in my right hand and pulled her head back by her hair. Not hard enough to cause any pain, but to let her know who was in charge. This position with her head now forced back and resting on my shoulder opened up her neck. I lovingly kissed and sucked on this newly exposed flesh.

Andrea has two sliding glass closet doors that make up one wall of her bedroom which are mirrored. I found myself watching us in the mirror and saw Andrea's facial expression. Her eyes were closed and her lips slightly parted. She was now deliberately pushing back against my cock with her ass. The desire to push her forward on the bed, raise her dress, lower her panties, and fuck her doggy style for all she was worth was becoming a hard feeling to fight. I commenced to sucked on her ear and growled softly, "Goddamn I want to fuck you so hard right now. I've wanted to fuck you ever since I met you." As I said this, I pulled her hard back a little harder causing her face to wince slightly.

Something came over me as I was a nanosecond away from plunging my cock into her little pussy. Andrea is friends with my wife and she and I have been friends for a long time. There was something "okay" and non-cheating about fucking her feet, but fucking her, as much as I was dying to, seemed like a very bad idea.

I pushed Andrea forward on the bed and positioned her so that her feet were hanging off the bed. I was still feeling dominant over her and she had been responding well to being dominated. I guided my hands up the backs of Andrea's smooth young calves. Raising her dress to her ass I saw that Andrea was wearing thigh-high stockings! Visions of her body wearing nothing but those black, ultra sheer thigh-highs as I fucked her in every position imaginable was hard not to think of.

My hands were now at the tops of her thigh-highs. They were close enough to her pussy to feel the warm and humid heat radiating from between her legs. The crotch of her panties were visibly wet. If I had pulled them off and fucked her, she wouldn't of objected. Inserting my fingers into the tops of her thigh-highs, I gently rolled each one down her legs until they were both around her ankles. Gripping the toe portion of each I pulled them and watched as they slowly exposed inch and after inch of her tender bare soles.

I'm looking down at Andrea's body on her bed. Her head is tilted down and her torso is up, supported by her elbows. This makes for a nice arch in her back. The bottom of her dress is still pulled up from her stocking removal which exposes her tight panty covered ass. Her legs are slightly parted and her soft size seven and a half feet hang off the bed.

I place her ankles side by side and use one of her stockings to tie her ankles tightly together. Once bound, I raise her calves at about a forty degree from the mattress. I'm holding each foot in a hand with my palms up. My four fingers are touching the tops of her feet and I use my thumbs to caress up and down her soles. My thumbs feel that soft skin under her sweaty little toes. Then the slightly rougher skin on her arches as I make my way down to her heels. Pressingly deeply into her virgin foot flesh with my thumbs.

Reversing my hand position so that I am holding her feet like one would a sandwich. My thumbs force her toes to point and point HARD. This causes her soles to wrinkle. The fingers of each and slowly rise and fall as I stroke up and down her milky white soles. Kneeling down and allowing her feet to relax I take her two big toes into my mouth. Sucking them lovingly and being able to smell her feet. The visual of all of this is getting to be too much. Holding her feet in place with my left hand, the right hand finds it way to my shorts and soon they are in a pile around my knees.

The first stoke I give my cock is almost enough to make me cum. Releasing him I stand back up and toss Andrea one of her heels. "I want to see you smell it." I say. Being a good girl, Andrea does so without hesitation. Seeing her pretty face with her nose inside her black heel is intense. She does it for a second then places the shoe back down.

Placing her calves back at the forty degree angle and supporting them with my left hand under her feet, I grasp my cock by the base with my right thumb and fore finger. I raise my cock vertically and then start slapping her soles with it. The slaps are hard and make a loud "thump" against her soles. I slap them a few more times and then lay it flat on the balls of her feet.

Thrusting my hips back and forth. Watching my cock slide down to her milky white arches. Guiding it side to side across her arches and then the balls of her feet. Moving backward and putting the head of my cock under her toes and sliding him back and forth. That ultra soft skin I keep talking about under her toes feels insane on the head of my cock.

Even though Andrea is receiving no direct stimulation besides her feet, she is moaning a little louder and softly grinding her hips into the mattress. "You want to cum, don't you baby?" I ask.

In a louder voice than I had been using, Andrea turns her head to look at me. She lets out a sarcastic chuckle and says, "Duhhhh!!"

"Good girl" I say, "Make yourself cum."

Andrea reaches under her body and I see her hips adjust and rise to allow her fingers to reach her wetness. It becomes obvious she makes contact when she lets out a loud sigh of relief.

Taking Andrea's other stocking, I use it to tie her tow big toes together. Tight enough that her precious little toes turn slightly blue. Bending her legs more towards her fine ass, I slide my cock in between her arches. I look over at this scene in the mirror and can't help smile at myself. Looking at us in the mirror is like watching a porn video staring Andrea. I relish the situation for a second as I look at us in the mirror. I can't believe that I have Andrea tied up on her bed with my cock between her feet as she is masturbating. This is a mental picture I'll remember forever.

I hold each of her feet in my hands in the position where my fingers are under her feet and my thumbs stroking her soles. The fact that her feet are bound is applying just the right amount of pressure to my shaft. My thumbs are there to molest her soles. I fuck her arches deeply and love how it feels when just my head is sticking up between her arches. I take some saliva and lubricate her arches. Now its time to fuck them ...and fuck them HARD.

I'm fucking Andrea's feet in a "soles up" position at such a pace that it could be argued that I'm raping them. Andrea is getting loud and is moving around on the bed in such a way that I have to hold her feet tight so that my cock doesn't dislodge from her arches. "I want to hear you cum Andrea, cum like the good little foot whore that you are." I say.

She is facing the pillow and saying, "Oh fuck, oh fuck, oh fuck." She keeps repeating it over and over. Controlling my own orgasm is getting to be an impossible and cruel task. I want to cum on her soles at the moment she cums. I've never heard Andrea have an orgasm, but when she slams her head into the pillow and buries her face in it and starts to scream, I have a sneaking suspicion that her moment is arriving.

12