I started wearing heels in a casual way as a teenager, really learned to like them and often wore them at home in the evening. Now as I was engaged to be married I had decided I'd better get around to throwing out the few pair I had. The problem started one night when I had promised to take my fiancée to dinner and a movie. She arrived at my house as I was just finishing dressing. I let her in and gave her a kiss, then said I was going up to put on a tie. I'd be right back.
"Oh, I'll help you pick out a nice one" was her comment and she came on up to the bedroom behind me. We've been in bed there before, of course, but I'd had always had the shoe cupboard locked. Without asking she popped open that cupboard thinking it was a clothes closet. Seeing my heels, she asked "Oh are these for me?"
"You're seeing another woman!"
"No, no definitely not. NO!"
"But then who's are these?"
"Oh wow, they're yours aren't they?"
"They are, aren't they?" and she grabbed up my nice classic black patent pumps. "Put them on, come on Brian, put them on. These'll look great with those grey slacks. Come on." Did I detect a bit or sarcasm?
Thinking the wedding and my life with her was finished I didn't know what to do. I took the pumps from her outstretched hand and sat on the bed trembling.
"Come on Brian. Put them on I want to see them with your slacks and blazer."
I slipped off one loafer and put my foot over my knee.
"No, not with socks on silly. If you wear them you must have some knee highs. You do don't you?"
"Um, yes," and I pointed to a drawer.
She pulled out a pair of tan ones. "These'll do fine," still sounding very firm about it all.
I put on the knee high and a pump.
"Both feet! Do both feet Brian!"
When I finished I stood up, still tremendously nervous and expecting to get my face slapped and my ring thrown back at me, but I stood up.
"They're beautiful. You look great. Now let me pick a tie to compliment it all and we'll go to dinner."
"Not wearing these," I exclaimed.
"Not to a restaurant, not in daylight."
"Oh, well then to the movie."
"In the movie then. If you don't wear them in the movie I'm not going out with you. We'll pick some secluded seats and you wear them while we watch the show."
"They don't let you take packages into movies any more."
"I have my big purse with me. Nobody will question a woman with shoes in her purse," she said taking the pumps from me and turning to the other door where she picked a red and gray tie. " Now don't be a nerd about this. I'm not taking no for an answer. No, no, just leave the knee highs on. You can wear them with your loafers can't you?"
"Well come on then, let's get going."
She seemed in a good, but no nonsense, mood. I hadn't been slapped or rejected. I went along with her request.
We had ‘everyday' conversations on the way to the restaurant, yet I felt I was being toyed with.
At the restaurant we had a nice meal, some great wine, and a good time. What was going on? Part way through the meal I felt her stockinged foot lifting my pant leg and rubbing against a knee high. God it was such a silky smooth feeling, wonderful. I was getting a hard on. In turn I slipped a loafer off and started to run a toe up her leg. Her eyes went wide and she looked at me with that doe like look she gets when she wants to be screwed. Was she also enjoying the caress of nylon on nylon, or was she playing me along for some big ugly ending later. My rod was so engorged I didn't think I'd be able to leave the table.
Later, as we finished desert and my rod had relaxed some, she reached for her purse. "Do you want to wear your heels to the movie now she asked."
"Oh Brenda. I just don't think I can do that, I mean……"
"Well you're not getting away without wearing them in the theatre." She was firm, almost demanding again, yet the doe eyed look was still there.
The walk to the theatre was pretty silent. Not icy really, but quiet as though she was thinking. Probably going to get me with the heels on and then scream out and draw everybody's attention to me and make me a laughing stock.
At the theatre, true to her word, she chose secluded seats near the front and to one side where we would be alone. Once the lights were down and the movie started she opened her purse and handed me my black patent pumps. "Now!" she said.
I slipped off my loafers, which she quickly grabbed and stuffed into her purse. I put on my pumps. They did feel good, but I dreaded the scene I expected to come. I tentatively took her hand, which she didn't reject, and settled down to watch the movie. Soon I felt the toe of her red slingbacks hooking my ankles and pulling them toward her. Then she intertwined her ankles through mine, our shoes now nestled together. Despite my fears of a scene my cock hardened. Brenda felt for it and slowly worked my zipper down. I knew there was going to be trouble, yet I was so aroused I couldn't bring my self to stop her.
With her hand wrapped around my cock we spent the movie nestled and touching. Each time I would start to wilt as I worried about what she might do Brenda kneaded me (or by rubbing nylons with me, and sliding leather along leather) brought me back to hardness, but never to the point I might come. Just a constant yearning in my groin for this experience not to end.
Yet, all too soon the movie did end. I cannot say I remember much of it, what with my nervous tension and my sexual tension. But I was left with that wonderful feeling of a plump cock filling my shorts – not that rigid hard bursting feeling that is the ultimate of manhood, but that blood filled fullness I'd like to have most of the time.
Brenda leaned over and said "Now do you want to walk out of here in those heels, or in your stocking feet, cause I'm not giving you your flats back.?"
I thought ‘Oh Jesus here we go,' but I didn't want to walk up the sticky aisle apparently barefoot either. "With heels," I whispered back.
"Good," was her response, and we set off, she holding onto my arm.
In the lobby she said, "Good going, now just through the door and on to the car."
"It's three blocks!"
"Are your shoes pinching?"
"No, silly, they are expensive pumps," I said without thinking.
"Well then? Come on, it's dark out here." and she nudged me on and no one seemed to notice me. "One, two, three, four… That's it, just keep going now."
Three long blocks of both fear and pleasure. I loved the sound of our heels clicking along together, now with my arm around her, our hips swaying in sync as only high heels will do to you, the feel of the shoe arch pressed against my instep. Three hundred and forty four, three hundred and forty five, three hundred and forty six – my brain had been counting off the steps. I stopped to unlock her door expecting a laugh or exclamation from someone on the sidewalk, but I waited to close her door, watching those beautiful red kid slings disappear into the car . Around at my own door, the lights of a car coming down the street flashed fully on the shiny patent. I expected a squeal of brakes and an angry driver to lunge out at me. Nothing! I was in the car.
As for my cock, I was so tense it felt like it had wilted to absolutely nothing. I couldn't remember the feeling of having a dink so small since I was a little kid.
The ten minute drive back to my house was occupied with talk of our wedding (which was a relief) and Brenda was even showing a bit of stocking top but she still seemed distracted. However, I had to keep my mind on driving – driving in heels was not as simple as I thought it would be. It got easier as we went and I learned to keep my ankles tilted, but still….. At last we were there and I was feeling more relaxed as I pulled into the driveway.
When Brenda carries her big purse it usually means she plans to stay the night, and I was hoping that would still be the case. She left it by the door, not a good sign, but I went to get us two glasses and some cold wine.
Settled on the couch she took her glass and emptied it in one shot. Not at all like Brenda. I refilled it and again she drained half of it. I pulled her toward me to cuddle, but she lay back, her head on my lap. The front of her blouse billowed open and inside I could see one of her hard pointed little tits. They push straight out like cones until the brown rings, then dimple in and start again until the tiny gum drop of her nipples. Delightfully my cock began to rise again. As she felt it happen she pulled her head back onto my legs, unzipped me and pulled it out to let it rise like a little monument. I slipped my hand into her blouse and I quickly went very rigid.
"Why didn't you do that in the movie? I was unbuttoned for you." she asked softly.
"I… I… I didn't notice. I'm sorry. I was a little uh distracted."
"It's OK. I wanted to discuss something with you tonight, um…"
My cock started to go limp. She simply flicked her tongue out and brought it back to rigidity. "Uh huh," I croaked, taking a quick sip of wine to clear the dryness.
"I uh .. You've never worn your shoes outside before have you?"
"No Bren. I haven't."
She was quiet for a while, just flicking my cock with her tongue from time to time, as needed. I finished unbuttoning her blouse with intentions of getting it off so both her hard cones would be bare.
Brenda usually calls me Bri when she wants something. "Yes." Sipping again.
"Bri, I want to…. Um, and so you've never been driving with them on either?"
"Not that either, no."
"Well you do it very well, I mean wear heels."
"Thanks." Sipping, sipping.
"How long what?"
"How long have you worn them?"
"Um, since I was seventeen I guess, but you know, only some times, at night."
"Ah." Flick flick flick of that cute pink tongue.
Her nipple had long ago returned to its proper position, extended. Watching her, feeling her tongue and being able to look past her head at my patent pumps coming out of the legs of my gray slacks made my cock tremble and a little clear juice started to dribble. "Yummy," she whispered, flicking it away
"Ah what?" I continued her earlier comment, trying to stop from coming.
"That explains why you do it so well."
Silence again, then "Bri I, … do you like my shoes?" she said softly extending her right leg straight up in the air, her skirt falling back to reveal her garter belt.
I moved my hand from her tit to her ankle and started caressing my way down the silky nylon. "Yes I do, and the red matches your blouse perfectly."
"Do you like the heels on them, or do you like your thin ones better. My um. A friend I know likes the little thicker ones and convinced me to buy them…. anyway, which do you like best?"
"I really do prefer thin heels," I said, but those are very nice. Maybe a half inch wide, aren't they? Thicker than that is ugly."
By now I had reached the straps of her garter belt and was working across soft white flesh to work a finger inside her panties.
"No Brian." She sat bolt upright onto the couch, now beside me. "No, I can't go on like this. I have to tell you…."
I had crossed my legs, almost crushing my balls and forcing my rod into even more prominence, while at the same time I had wiggled my toes to dangle my right pump, in an attempt to appear casual. It obviously didn't work.
"… I have. I have a secret too. There is a girl, no a woman," she croaked in her frustration to express properly what she wanted to say, "that I…. go to bed with."
‘Huh, that was it? That was what this had all been about,' my brain said. And I thought lots of women did that.
"And?" I said wiggling my shoe.
"And you don't care?"
"Of course I care. I care that she treats you well. I'm not disturbed that you enjoy another woman's body or she yours. I thought that plenty of women enjoyed each other today. As long as you and I still enjoy each other I'm OK with it."
"Jesus," she shouted, jumping off the couch to stand in front of me legs spread, hands on hips, both tits staring me straight in the face. "And I've been struggling for a week to figure out how to tell you, and then tonight, your shoes, and trying to nurture you to wear them with me…" Sparks jumping out of her eyes, she turned and paced to the door and picked up her purse.
I thought she was going to leave. Instead she turned and came back, tits thrust out. She dug my shoes out and put them on the table, then dug out her night clothes, and last took out an unopened pair of black stockings.
"Here," she said, thrusting them at me, "take off your trousers and shorts and put these on instead of those knee highs." Then pushing her panties down, so I caught a glimpse of bare slit I been intending to reach only minutes before, she said, "Then put these on to keep that thing of yours under control until I get back."
"I don't have a… a garter belt Bren."
"Those are my ‘spares'. My ‘spares' always have elastic tops."
Taking my loafers with a "You won't need these again tonight," comment over her shoulder, she went upstairs with her night clothes.
I worked at slipping the lovely stay up stockings up my legs without getting a run in the very sheer fabric and eased my feet back into my pumps. The panties I pulled up over my hips and although they would contain my semi soft rod, they scrunched into my bag, pushing my balls until they wear appearing out the sides. This was not comfortable at all. I finished my wine and waited.
Brenda returned wearing a black nighty that clung to her body, its smoky transparent top only emphasizing the beauty of her tits. Over her shoulder she had slung the coat to go with it, hanging it over her thumb. At the sight my cock sprung back to fullness and popped out of the top of the panties.
"Here, stand up and put this on. My those stockings look great, and your knob looks so cute peeking out like that, but I can see the panties just don't work. And now I can see that the peignoir doesn't look right either without boobies to push it out. I could do something about that, but not tonight … hmm. Okay, take the peignoir and panties off, then sit back down.."
I did as I was asked, then Brenda said "You do have a condom in your wallet don't you?" and I nodded.
She ripped the little package open and forced it down over my engorged cock. Then she carefully lowered herself down onto me, folding her legs so they were up beside me, her red slings now resting on my shoulders. It took a lot of concentration to stop from coming just then. She was literally impaled on me.
"Now that's comfy," she cooed. "No, keep your hands off my tits until I've said what I have to. Here's my deal. You get to keep your pumps…., if you will agree to wear them out with me more." I nodded agreement. "And," she went on, "if you'll let me keep my girlfriend. Deal?"
"Deal!" I gladly agreed.
"OK," she said easing off of me to stand, "Let's go upstairs and fuck!"
I love taking stairs two at a time in heels, and watching Bren's red ones flashing ahead of me just added to my desire.
We crashed onto the bed and she pulled her lips wide, wet and ready to take me. I drove into her and nylon swished against nylon. The feeling of shock rolled up my legs and into my groin. She must have felt that same excitement too for she bucked under me and we both came, yet continued to thrust until at last I slumped back onto the bed.
When our breath returned, I rolled to my left and began sucking one of her wonderful tits. She began to knead my cock. "Bri?"
"Those white pumps of yours I saw, the ones with the metal heel..?"
"Are they new?"
"Do you think the store would still have any?"
"I'd like to buy a pair. We could wear them together then. Couldn't we, huh?"
I said "Yes," but I didn't need to answer because she already knew. My cock hardened again at the idea.
Quickly I applied a new condom, as Brenda removed her nightgown and rolled on top of me this time. We had a long slow coupling as I played with both of her tits, watching the nipples swell and swell until her eyes started to go wide again and she arched back away from my hands to let out an ecstatic cry of joy. With that my own load emptied. I wished it had been right into her. In a few weeks it could be that way.
A few minutes later I sat up to remove my heels and her stockings. "No, don't do that Brian. Sometimes I sleep with my shoes on, it's sexy. Have you never done that?"
"Well, this is a good time to start. Come on, it's time for some shut eye."
Two or three hours later I woke to find us coupled like spoon, her butt into my belly. I could feel one of my heels touching hers. My cock started to rise once more. Brenda felt it pushing into her legs and eased them apart to let it grow into her. Soon it was nestled into her crease and she was playing with its head, like it was a short cock of her own. Then she rose up on her knees and asked me to take her from behind.
Another fresh condom and the third fuck of the night. We had never copulated this much in one night, but I was certainly ready. This was also a new way for me and I went at it slowly. I couldn't get in as far, but Brenda seemed much more stimulated this way. Nylon was always next to nylon and she locked her heels over mine. I bucked into her over and over and could hold off no longer but she must have known I was coming for she pushed away back into me then cried out and sagged forward.
Exhausted now we lay side by side just fondling. God I love those tits.
As I was once more dropping of to sleep she whispered "Bri?"
"Have you ever thought about having your balls off?"
I sat straight up in bed and unconsciously covered them with my hands. "Good God no! I know we don't want any children, and I have an appointment next month for a…"
"No, no, its not that. I just thought the panties would fit much better without them in the way."
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