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I Lost My Virginity Wearing Stockings And Heels

I remeber it as if it were yesterday. I was seventeen and had been dating Jason for about 8 months. He use to get very playful when I wore dresses and would always try to feel me up. Especially my legs. I always wore pantyhose with my dresses. I knew he liked them and he definitely didn't try to hide the fact.
At that point I had never actually worn stockings. One afternoon my aunt came over. She was really cool and I told her everything. We were talking about Jason and I told her I wanted him to be my first. I wanted it to be really special. She was very supportive and was always a help. She told me she had just the thing for me. Later that night she stopped by briefly and dropped off a package for me.
I went into my room and shut the door behind me. I opened the box to find a gorgeous royal blue garter belt with black lace trim and a matching under wire open bra and the last thing in the box was a pair of back seemed black silk stockings. OMG they were so soft.
I jumped in the shower and then did my hair and an extra special job on my makeup. Then I put on the beautiful outfit with the stockings. The bra was very different for me. It had under wire and lift but my breast were totally bare to the front. My nipples got hard as I was looking at myself in the mirror...A little embarrassing...The garter belt had little short straps that held the stockings good and hi. I just loved it. I went to my closet and picked out my knee length black leather skirt that zipped up in front and right up the middle of my left leg. Then came my satin royal blue blouse and to top it off my black stiletto open toe heels with a thin ankle strap.
Jason and I were going to the movies that night and at 630 sharp he arrived. I seen him pull up out front and rushed out the door to meet him.
We arrived at the movie (Ghost Busters..lol) and went in and chose seats at the top, all the way over in the right corner. As I sat down I unzipped the front of my skirt to just above mid thi. I then crossed my legs and to Jasons surprise the top of my stocking popped out in plane site for him. His hand immediately went to my leg. I seen the smile on his face when he felt the silk. So much nicer than the legs pantyhose. I also noticed an instant bulge between his legs.
We watched about twenty minutes of the movie and he just could not keep his hands off me. Finally I took his hand in mine and placed it on my leg and then guided him up past the top of my stockings and to his surprise, right to my vagina as I wasn't wearing any panties. The blood rushed to his head and he became flushed and I think he almost passed out. He grabbed my hand and up and out the door we went.
We had a little place at the local lake that we often walked and he actually got to third base a couple times..lol That was where we went. Jason took our blanket from the trunk and laid it out near the water. I stood in front of him as he kissed me passionately moving his hands all over my *** as he worked them around front and started unbuttoning my blouse. My blouse came off quickly and he was so into my bra with my breast exposed and setting high for him...He kissed and sucked my breast as I unbuttoned his shirt and slipped it down his arms till it fell to the ground. Then with a slightly quick move I ducked my head in and started sucking his nipples. I didn't know what I was doing but to my surprise he was really in to it. I started undoing his pants and then dropped them to the ground and my hand found him rock hard...He laid me down on the blanket and fiinished unzipping my skirt and I could feel his passion as he gazed and his hands worked all over caressing my stockings. he moved his body down and started kissing my legs and then he had both of my ankles in his hands as he kissed my feet and toes...It was a little wierd I thought but felt amazing....He kissed his way back up my stockinged legs holding my ankles the whole time until he arrived right at the top of both of them and started kissing and licking my vagina..At first I thought eww how nasty but then I thought oh my god that feels so good. He stayed there for a few munites licking and sucking and I was just so into it. I had this incredible feeling come over me and then my body went stiff and I was moaning with pleasure and wow it was incredible as I orgasmed to his licking. He then moved slowly over top of me. My legs were spread and wrapped around him loosely. He began to kiss me as his muscular body dipped in the middle and I felt his manhood reach its entry point. He slowly worked it in and while it hurt at first, he was careful and worked it in gently. When he was totally inside me he stayed there for a couple minutes and kissed my neck and then he gently lifted my stockinged legs over his shoulders so he could feel, caress and kiss them. Then he started pumping nice and slow. Oh my god it was incredible.. in and out and mmmmmmmmm it was so good and then he picked up a rythm and slowly increased the pace more and more until he was pumping full. All the way in and all the way out and the pace was gentle but fast and I was just totally lost in the passion as he pumping me and kissing one leg while caressing the other as my legs held his bodt in place. I started feeling it again. The pleasure was welling up in my loins and I began to buck with him and then my body went stiff and as I was orgasming he pulled out his manhood and shot his ***** all over me.
Wow it was really passionate and he was gentle. It was a great first experience and Jason enjoyed those stockings many more times.
cherylteaks cherylteaks 41-45, F 11 Responses Feb 8, 2013

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Loved your story.. Reminds me of the Prom night I took my GF's cherry and the feel of her silky stocking legs wrapped around my back. Add me please.

Good times , Love your story and candor... Looking forward to more of these arousing , inspiring stories... Sd

I love stockings and heels. Shelf bras put me over the top
Please add me as a friend.

What a fabulous story. Royal blue is my favorite color

I so enjoyed your story

No wonder you like stocking. Did you repeat after that night with stocking again?

Yes...Many times.

Sound like you enjoy sex in stockings and heels

Terrific story! Is it me...or did it suddenly get warm in here? LOL

I have that effect on people sometimes......

"It was a great first experience and Jason enjoyed those stockings many more times." Wow! What a wonderfully sexy story. Your aunt gave you thee best advice! I'm sure you were stunning and looked SO sexy in those seamed stockings. I wish I'd been your boyfriend that night. I would have been in heaven - complete heaven... You're a wonderful caring woman, have lovely legs and know how to drive a man wild with your lovely stockinged legs. You're amazing. Take a bow pretty one!

OK you are definitely too kind but I will take a bow just for you......

Thx! It's just that you're perfect to me. I mean that. Imagine the fun we'd have if we were both single! You'd have me under your control and I'd be the happiest guy alive.

"I will take a bow just for you." Yeah! You deserve it. Do you have any idea how perfect you are to a guy like me? You're a nylon fetishist's dream. I hope I spelt that right!! You're perfect Cheryl Ann.

I realize that you love stockings hon but I am really far from perfect. Last year when I slept with the so nice crossdresser, I cheated. It was the only time in twenty years but none the less I cheated. I am not perfect. Of course I could say his stockings made me do it...lol

I don't care. That doesn't bother me one bit and I know that no one is perfect. I also cheated on my girlfriend (who later became my wife) when I was 21. An old girlfriend came to town and she knew about my fetish and had bought some lovely stockings. I was very horny and we were having fun and she got up and put them on for me. I was wowed. She just wanted me to have fun and gave me a ******* and then let me c*m in her mouth. It was heaven and nothing like it has happened since I've been married.

My big mistake was telling my girlfriend and thinking I'd feel better. It was just the reverse. I've learned from that. I think I married the wrong girl.

"Of course I could say his stockings made me do it." Really? So you like it when a guy wears stockings too? Wow! You're fun and I'd love to do that with you.

To me, you're perfect in the sexual sense and your legs in stockings are wonderful and yes, perfect!

Well his legs were shaved nicely and he was dressed very classy and in my opinion really passed as a woman and I was flattered by his interest in me.
While in a sense a hand job is cheating, I did it all hon.......Everything!!!!

That's okay. I'm sure you had your reasons for doing it. I've learned that it's too easy to judge the person who does the cheating without asking why they did it. Everyone has their reasons. I've met some women on EP and have learned that they had good reasons for cheating. I had good reasons that day with my old girlfriend. That was an amazing day and I've never forgotten it.

I feel comfortable with you and if you wanted me to crossdress or dress in nylons, I could easily do that for you. I'd even shave my legs for you. I still think you're amazing and VERY sexy Cheryl Ann.

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very sensual well put

Thanks hon....It was very sensual.. I think it is why I like stockings so much.

thats good do u still wear them

almost evryday hon...

thats great darlin

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Lol I am glad you liked it. It is truely my first and it happened in 1981. Amazing how times dont really change for some things. I just remember how totally sexy I felt wearing those stockings. I was very nervous but I think the stockings and garter set led me thru to my ****** and sexual experience. I wear them very often and love reliving my first experience in them...Men pay so much extra attention to me also...Hmmmm my aunt was very young in the late 50s and 60s........lol

"I just remember how totally sexy I felt wearing those stockings." OMG! You're amazing!

"I was very nervous but I think the stockings and garter set led me thru to my ****** and sexual experience." Wow! What a very sexy woman you are.

"Men pay so much extra attention to me also." That's me - exactly. I'd be so happy and would be putty in your hands. It would be heavenly. You have wonderful legs and are beautiful. YOU are perfect Cheryl Ann.

I am sure you would have been great hon.... I really try to be sexy....But I do it the way I want to. I feellike I am so lucky. I love lingerie and always have. I feel like I dont have to compete or beg for attention. It just gravitates my way. I was at an out door bar one time at mid agternoon. I was wearing a pair of full fashion french stockings and noticed I was getting a lot of looks. Not only from the men but the women too. So I thought I would have some fun. I took off my heels and started rubbing my feet. As I crossed my legs to bring my foot up to rub the top of my stocking would just slightly appear. After a couple minutes one woman slapped her man and another got up and grabbed her mans hand and left. A couple minutes later the bar tender brought me three drinks.....It really is powerful and yes I was being a naughty girl.....But it was fun..lol

"I was wearing a pair of full fashion french stockings and noticed I was getting a lot of looks." OH MY GOD! Seams! Cheryl Ann!

"I love lingerie and always have. I feel like I dont have to compete or beg for attention. It just gravitates my way." I'm sure it must! You would be so easy for me to love and admire and lust and thank my lucky stars for. It would be fun to watch other guys being so turned on by you.

"As I crossed my legs to bring my foot up to rub the top of my stocking would just slightly appear." I've met an angel !!

"It really is powerful and yes I was being a naughty girl.....But it was fun..lol" Good for you. I wish I'd been there that night. I honestly wouldn't have been able to keep my eyes off of you. I would have been so happy. And I would have wanted to see as much of you as I could. I mean that. You're wonderful and incredibly sexy to me!

What a beautiful picture you draw. Growing up and dating in the late 50/60's you have captured the magic of discovery that I had experienced-very vividly, thank you-can't wait to read more.

I am glad you liked it. It was my first and I love thinking about it. I really do remember it like it was yesterday. The movie wasn't ghost busters though...It was a re-show of star wars...lol Jasons idea.