I Visited My Sister In-Law

Story Info
I visited my sister in-law and got a naughty surprise.
3k words
4.46
165.1k
73
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
SarahCD
SarahCD
401 Followers

I went over to my sister-in-law, Alison, for a casual chat. We had always got along really well. She was my wife, minus my wife's attitude towards me. We sat in the living room and chatted over a glass or two of wine. Then the buzzer on her clothes dryer went off. She said, "I need to fold my clothes while they're still warm."

I followed her into the laundry room and watched while she unloaded the dryer and separated her clothes into categories and started folding them. We just chatted on. My eyes kept going to the pile of her panties waiting to be folded. They were in bright colors with lace trim and lots of bows. My wife would never have worn anything that sexy and skimpy. I started to get a strange fascination in them and realized that I was getting an erection.

I think she glanced at my crotch and noticed where my gaze kept going. She moved to start folding her panties. She picked up a nice frilly black pair and suddenly held them out to me and said "There, these should fit you, try them on."

I stammered and blushed but she said "I know you want to, go on, put them on." I took them and held the soft lace between my fingers. I was so excited but scared at the the same time. I was holding a pair of frilly girl's panties and my siste-in-law wanted me to put them on. I was so confused and excited at the same time. I had to put them on. I went to leave but she said "No, change here, in front of me, I want to watch you."

I was so excited about wearing her panties that I didn't care if she watched. I undid my belt and took my jeans off. I pulled down my shorts. I was very aware that she was staring at my very erect cock. I quickly slipped on her panties and put my jeans back on.

It was a wonderful feeling. Girl's lace panties around my cock. It was electric. I was actually wearing girl's panties under my jeans. I could have cum just by thinking about it. It took me a while to fully accept what was happening. I was wearing girl's panties.

She continued to fold her clothes and we did not mention panties again. It was as if nothing special had happened. When she was done we went back to the living room for another glass of wine. It was hard for me to maintain our conversation knowing that I had on girl's panties. It was so erotic. I was wearing girl's panties under my jeans and pretending to be quite normal.

She said "I need to go shopping later, can you come with me to help carry things?" I said, "Sure."

She added, "If you ever don't do what I tell you too, I'll tell my sister all about this". My sister will love to hear all about her sissy crossdressing husband. My blood froze; I realized that I was totally under her control. Somehow it was kind of exciting. I wondered what more she would make me do.

She said, "Let's go shopping."

I was still wearing her panties under my jeans and it was hard to keep my erection hidden. I was actually wearing a pair of girl's panties out to the mall. I imagined that everyone could see them even though I had regular men's jeans on. It was as if everyone was staring at me.

By now it was Saturday afternoon and the stores were full with customers. She went into a lingerie store and she just looked around. A saleslady came up to us, "May I help you, ma'am?" Alison turned and smile sweetly, "Yes that would be nice. It's for him. He needs some new lingerie."

I turned beet red and started to shake and mumble and turn away. Alison put her hand on my arm to keep me in place. The saleslady was flustered. She noticed two things: the credit card in Alison's hand and the bulge in my jeans. I guess that a sales commission trumped over social norms.

She found some nice things for me. Alison said, "Why is it that men have no idea about colors and patterns; about how to match and complement clothes. I will have to spend time teaching you how to create matching sets, bras and panties with camisoles and dresses. It will be so much fun!!" Then we can work on accessorizing, getting the right purse and belt for a particular outfit. Then we come to jewelry and makeup, more lessons for him or is it her? What color eye shadow works with a peach dress and there's so much more to learn.

She whispered to me, "If you ever disobey me, my sister will love to see your new wardrobe."

We paid up with all of the items laid out on the counter in front of us. It only added to my embarrassment but also a strange sense of excitement. I loved my new clothes. The colors and textures looked so sexy. I wanted to try them on, my cock was hard just thinking about wearing them. Would she make me wear them in front of her?

I let my fingers feel the lace and satin, such soft thin girl's clothes and they were mine. I would be putting them on later.

Alison said it was her treat to me for being a good girl. I kind of liked being called a "girl". It had my cock jump.

She asked the assistant where the changing room was and handed me a bra and panty set and gave me a shove. I had to carry them into the changing room and put them on.

Then she took me to Dress Barn and I made me pick-out a dress. I chose one with short puffy little sleeves in white and pink. The puffy sleeves hid some of my male shoulders. It had a straight bodice and a floral skirt that poofed out. It had petticoats underneath to make it spread out more. She made me go and try it on. I had to get the assistant to unlock the changing room door for me.

It was a wonderful feeling when I slipped it on. A girl's dress just felt so electric against my skin. My panties were free to the outside under the petticoats. I was so excited and scared at the same time. I was getting electric feelings wearing a girl's dress. Even the words shook me, I was wearing a girls panties under a girl's dress.

After she paid for my new dress, she said "Go and put it on". I had to take it back into the changing room and slipped it back on. I was surprised, it felt wonderful. The dress just rubbed against my body and I loved the way the skirt swished against my legs. I tried sitting down and it was wonderful to feel the petticoat against my thighs. At least it hid my erection.

Later as we walked around the mall, the petticoats brushed against my legs. I admit it was a wonderful feeling. I could feel the air conditioning blowing under my dress against my new panties.

Before we went for lunch she looked at me and said, "We had better do something about your face." She took me to a makeover place in a store. If you bought $60 worth of their make-up they would give you a free make-over. I had to sit there on the high salon chair while my makeup was done and people walked by seeing me. Not only was I wearing a dress but getting my makeup done too.

I had to put my head back while she powdered my face. Then she did my eye makeup. I did enjoy it when she did my eye-liner. Just a black line just a above my eye. It felt so cold at first.

Alison said, "Before we go for lunch we need to name you. You shall be "Amanda". I kind of liked the name, it suited me.

We had a light lunch, her treat. The Maitre d' treated us as just two girls out for lunch together. We sat and chatted. I admit it felt exciting and sexy being in a restaurant dressed as a girl. People passed by and took me for granted. I had an erection the whole time. I was in a dress, out with people seeing me.

I had trouble maintaining our conversation. I was so confused. I was dressed as a girl, I looked like a girl, I was being treated like a girl. I loved it. My every sense was on fire. I could feel the dress against my legs; the lace of the panties around my cock, my bra across my chest. My senses were on fire.

It was such a wonderful feeling. Sitting there, dressed as a girl, looking like a girl, out in public; sitting with my legs crossed and my dress tickling my legs; a wonderful surrealistic experience. I got lost in my thoughts more than once. I was a girl.

When I had to go to the restroom, Alison took my arm and led me to the Women's room. We went in together. It was decorated in cool pink with real flowers beside the sinks; so different from a Men's room. I took a stool and realized that I would have to sit down to pee or it would make too much noise.

We paid up and headed for her place. She wanted me to model the other new clothes for her. I had to put on each outfit right in front of her so that she could get a good look at my cock each time. She could tell that although I had no choice in the matter I still loved every pair of panties I tried on.

My wife travels a lot on business and so I started spending a lot of time with Alison. I had to model for her. She said that there is something uniquely virile and masculine seeing a strong Alpha Male in delicate lingerie. She liked me in softer pastel colors and flowery patterns.

I acquired quite a collection of panties and bras. Each pair I had to pick out for myself and ask the assistant if I could try them on. It was so exciting going to a new lingerie store that she had found, knowing what she would make me do.

She even watched me masturbate. She whispered tender words of encouragement. She made me lay back to masturbate, just like a girl. I had to lift up my dress or skirt, slip my panties down and lay back to rub my cock. She loved to watch every stroke. She could always tell when I was about to cum. Then I would shoot cum all over my stomach.

She said that her hardest task was to re-teach me how to masturbate. She said that "Pretty girls do not "jerk off"" Girls do not stroke and pump savagely at their pussy. She taught me to dress up really pretty in panties and a bra. Sometimes I wore a delicate bow around my penis. Women don't masturbate standing up. She told me to lean back and relax. I gently and slowly rubbed myself. An abundant flow of pre-cum does wonders. I used one finger to gently and slowly slide over and over it in smaller circles and larger circles. I slid my hand down and back up: slowly and gently, no rush, no hurry and gently. It was OK to ejaculate, it's perfectly OK to let her watch.

We had a secret email account for communicating. She called me "My Sissy!"

One day I arrived to find her wearing a short red pleated school girl skirt and a white blouse tied in a knot on the left. My wife would never have worn anything so naughty and provocative. She told me to come upstairs with her. She had a surprise for me. I followed up behind her and I am sure she let her panties show at every step.

In her bedroom was a sheer lacy red teddy nightie lay on the bed, she told me to strip and put it on. I did. She looked at me and smiled. She said, "I want to make love to a girl, Amanda. Kiss me."

I was so excited to try on the teddy I raced to take my clothes of. It was quite normal to me naked in front of her. I felt an odd feeling to try on her school girl skirt. It was so short and looked so naughty. I wanted to feel it around my thighs. I had come so far. Now I wanted to be a naughty sissy school girl.

I moved forward and we kissed deeply and with passion for the first time; before, it had been more of a friend's kiss. Now I had become a girl kissing her lesbian lover. Two naughty girls wrapped up together. I lifted up her skirt and felt her butt through her panties. A pair I had probably worn before.

She said that she loved seeing and feeling my pussy through my thin girl's panties. They made my cock feel so naughty; a man's cock in frilly girl's panties. It was such an electric feeling. It was like the first time I had regular sex. I could hardly think of anything else but dressing as a girl.

We kissed as we fell back on the bed. I could feel her hands going down my back and feeling my wispy panties. I pressed my cock against her pussy as we kissed and cuddled. It was so erotic knowing that I had previously worn those very same panties.

I didn't feel that I was being unfaithful to my wife. It was Amanda having sex with her lesbian lover, Alison. My wife was just a vague memory at that point. When I was with Alison I became Amanda.

I pressed my cock against her pussy as we kissed. There was just a wisp of lace between us. I slid my hands inside her panties and squeezed her butt. I pulled away from her just a little and smiled at her. We both knew where we were heading and we were both happy with it but in no rush to get there. We wanted to enjoy every moment.

I moved my hand round to the front of her panties and rubbed her mound. She moaned as we kissed again and pressed together. I undid the side knot on her top and pulled her blouse off. Her bra was so thin I could see her nipples pressed against the lace. I reached behind her back and unclipped it.

She smiled at me and it was her turn to pull away. She put her arm across her crest and looked at me with a naughty grim. She let her arm drop and her bra fell away reveling her breasts. They were so cute, pert little B cup; with lovely little nipples sticking up at me.

She slid her hand around to the front of my panties and gently squeezed my cock. She whispered "I love a hard cock in sissy girl's panties. Do you like the feel of lace against your big hard erection? You sissy girl you, I know you do."

I did love this new found feeling. Wearing girl's clothes had become part of me. When I dressed as Amanda I became a different person. She gave me the freedom to become a whole new person; a clean start. Amanda was now part of me. She was always sleeping in the background as I went around as a guy. I would never be the same again. I am now part girl.

I so wanted her to slide her hand inside my panties and I know she knew that was what I wanted. She looked at me and waited. Then she slipped her hand inside my panties and took my cock in her hand. She gave me a squeeze and started rubbing my erection.

We kissed again. My tongue mimicked what my cock was about to do to her. We knew what was about to happen and the anticipation made us both so hot. She held my cock as we kissed again. I pulled her panties down and I let her pull my cock out from the side of my panties. I positioned the head of my cock against her pussy kips and stared at her as I slipped inside her.

It felt like sliding into a warm welcoming cave as I went deep. Her pussy clenched around me and made me shake. I was a girl having sex with her lesbian lover. We shifted around and she sat up on top of me; her full weight pressing down on me; her full weight on my pubic bone. She was taking my cock deep inside her. I put my hands up to fondle her breasts. I love cute little breasts with pert little nipples.

She sat on top of me clinching her pussy muscle around my cock. I put my hands on her hips and pulled her down to me. She threw her head back and let her hair hang down her back as we fucked together. I knew I was going to cum soon and so I moved her around and lay on top of her.

It was my turn to push deep as we both felt our climaxes coming. We came together. Her pussy gripped my cock as I filled it with my cum. I pressed down on her as the last pulses of my cock teased her pussy. We fell sideways in each other'as arms, kissed and just held each other.

I now live a double life. Every few days I become Amanda and make love with my lesbian lover. I became a new person when I became Amanda. She had become my second self. I am proud to be Amanda. I had become Amanda.

SarahCD
SarahCD
401 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
20 Comments
SissyCrissy6245SissyCrissy6245over 3 years ago
Maybe a "Part 2" ???

Satah, another wonderful "tail" from your experiences. Christine thinks a chapter 2 with Amanda's Wife discovers hur and Allison together would lead to the Wife admitting a Lesbian experience in middle school. Then they could enjoy a Lesbian "Slumber Party" ...practicing makeup...talking about Men and their delicious COCKS. Maybe a separate story/experience....Mmmm ;-)

AnonymousAnonymousalmost 4 years ago

could have been longer. would have liked to see how the wife reacted to his dressing

AnonymousAnonymousabout 5 years ago
disappointed

I loved your story, but was disappointed to learn Allison was a real girl and not a CD or tranny. The first story of yours was when Sarah went to the Everglades and it really turned me on.

AnonymousAnonymousabout 5 years ago
Nice story

My wife plays dress up with me.

We started with me taking her panties off her and putting them on me before fucking her silly. We now dress up as sluts and go out partying sometimes. Last beach trip had my hot pink bikini and a short white tee in platform heels at the window getting a banana split for two.

AnonymousAnonymousover 5 years ago
beautiful

I read this while wearing my maroon leotard and pink tights and black lacy panties underneith. i love dressing up and having fun by myself when my wife is not home.

Show More
Share this Story

Similar Stories

Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
More Stories