Pretty in Pink Ch. 03

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Husband continues crossdressing.
2.1k words
4.58
63.6k
36

Part 3 of the 6 part series

Updated 06/08/2023
Created 09/24/2016
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jealouscuck
jealouscuck
2,576 Followers

After our trip out of town, Jessica and I had an even better sex life, if that was even possible. One night we ate out as man and wife and she made me stop at a dark, lover's lane type place. I had not really noticed before, but she had dressed rather conservatively. I just assumed that it was some of her new work clothes. When we got parked, she said, "Oh, my, are you planning to try something while we are all alone in this dark place?"

It took several more hints for me to realize that she was playing the demure little conservative female role. I moved over, placed my arm around her and began trying to kiss her. She pecked me on the lips and acted very un-aroused for a time. As I nuzzled her neck, she let out a nervous moan. This continued on as I made small advances just like a teen age boy would do. She gradually became more "aroused" and began breathing progressively heavier. Feeling the whole scenario then, I placed my hand on her knee. She put her hands over my hand. I could not tell whether her action was to stop my hand or to just touch me. She was absolutely playing a part of a sixteen year old virgin out parking for the first time.

I continued to kiss and nuzzle her until she took her hands off mine. I slowly slid my hand up her stockings until I reached the bottom of an old style girdle. (Jessica has a gorgeous ass and does not need a girdle). This came down to mid-thigh and had the stocking snaps up under the girdle. Just as I reached further, she guided my hand out and up to her breasts. She does wear a bra most of the time, but this felt heavy under her sweater. I massaged first one and then the other breast through the thin sweater. I then reached my hand under the waist band of her sweater and began feeling her bra encased breasts. I later found out that it is a vintage bullet bra.

As I felt her up, she moaned a little more and with more enthusiasm. I felt under her breasts and guided my hand under the band, stretching the elastic band enough to place my palm over her ample D cups. She kissed me more urgently and breathed more heavily. I pushed up the bra above her breasts and pulled her sweater up high enough to expose them. I took each nipple in turn into my mouth and tried to pull her whole areola in with the nipple. She moaned and squealed.

Jessica then interrupted me and guided my hand back under her skirt. I complied and started my journey back up her sheer stockings. I traced the outside of the girdle up to the Lycra encased honey pot and rubber her vulva aggressively. She moaned more and more.

Then she said, "God, Baby, I am so hot. Please take me home and fuck me."

I drove quickly home. She had re-arranged her clothing just like a real virgin would. When we got to our bedroom, she played the role all over again. She let me fondle her just as she had when we were parked in the dark. Eventually I took all her clothes off and mine as well. I mounted her missionary style and inserted my little cock into her dripping hole. I came in under a minute.

Now I was disappointed, but she wasn't. After a two minute rest, she said, "Thanks for the fuck, Loverboy, now get down there and eat my wet pussy."

I got down and began licking her cummy pussy. She responded with moans and, "Oh, yes, Baby, suck your cum out of my hot pussy."

With little doubt about her instructions, I did just that. My cum tasted quite good. I would not say sweet, maybe a little dull metallic taste. The whole experience was making my brain spin like I was on a drug. She had let me seduce her and now she was demanding that I service her pussy with my mouth. I licked and sucked her to three maximum orgasms until she finally allowed me to come back up. We snuggled naked and fell asleep.

The following week, she called me while I was driving home from my sales trip and asked if I felt like eating out again. I was eager to get home and relished a good meal, good drinks and time with my sexy wife. When I got home, she told me to shower and shave. She was dressed in a pair of cheap jeans, loafers and flannel shirt. Her hair was slicked back and parted on the side. Of course, she looked hot as hell still, but I got the message when I entered our bedroom and found my outfit laid on the bed. I was the same outfit she had worn the week before. Exactly, except the girdle was a figure enhancement shapewear model. I quickly showered, shaved and removed what little body stubble I had.

After showering, I applied my dusting powder and perfume. I dressed in the clothing, including the bullet bra. I added the breastforms. It did not push the breastforms in quite the way it had encased Jessica's soft breasts, but under the sweater, it looked good. I put on a white thong and then pulled the stockings up. I fastened them to the holders and pulled the shapewear girdle back over the stocking tops. I added a conservative pair of three inch heels and a brunette wig.

I applied my own makeup. It was tasteful, but slightly understated. I used mascara and eyeliner and very subtle eye shadow. I little pink lipstick and I was almost ready. Jessica kept pacing and asking aloud, "What's taking so long? Let's go already."

We ate Mexican food and had a couple of margaritas. I acted very feminine. To be honest, the most curiosity we aroused was from Jessica dressed in male type clothing. I just did not look like a man in drag. Jessica assured me of this as she always does. We both went to the ladies room between drinks. I did not arouse any suspicion and Jessica could never be mistaken for a man.

Jessica drove her SUV and on the way home we stopped at the lover's lane we had visited before. She pulled over and turned out the lights. She put her arm around my shoulders and kissed me. This time I was the proper and demure one. In due time, she placed her hand on my knee and began rubbing my stocking encased leg. I gently held her hand trying to be coy and proper. She was not to be deterred. As she moved her hand further under my skirt, I let out a slight moan. She reached the bottom of my shapewear girdle and ran her finger underneath, toying with the stocking snaps as she massaged my inner thigh.

To stop her momentum, I gently took her hand from under my skirt and placed it on the mounds of my bullet bra and sweater. She gently massaged my breasts and moved her hands down to the waist band of the thin sweater. When she ran her fingers up under my sweater, my stomach cramped from the gentle touch. I moaned a little more low pitched this time. She moved slowly up until she placed her palm over my bullet bra cup. She firmly caressed each breast while I continued to breathe faster. She French kissed me and I pulled her tongue into my waiting mouth. I lay back against the passenger side door, spreading my pretty legs a little wider as I did. She lifted my skirt and caressed my legs. She moved higher and higher until she reached the V between my legs. My panties and girdle were so tight that there was no way any blood could get through for me to have an actual erection.

I did feel a general tightness at my man pussy as she massaged me. She ran her fingers well under me and passed across my girl cock stuffed firmly under my feminine underwear. I was moaning like a bitch in heat now.

I said, "Oh, god, honey, I want you so bad. I would love to feel your cock in my girl pussy." We went on this way for awhile. I would have shot my cum if I wasn't so bound up. Shortly, Jessica moved back to the driver's seat and cranked the car. We drove home.

When we entered our bedroom, she held me close and pulled my ass to her groin. She rubbed my ass pads and moved her hand to the front to finger my girl cock. She unfastened my skirt and I let it fall to my shoes. She rubbed my V as I moaned and hunched forward to her hand. She then pulled down my shapewear girdle after she un-hooked the stocking tops. She excused herself to go to the restroom. I was wondering what she had in mind. I did not have to wait long. She came out wearing a leather cock harness with a six inch long chocolate colored dildo springing erect. She had on a leather bra that pushed her magnificent breasts up and almost out. She wore fishnet stocking and black high heeled boots. She gave me a pair of black crotchless panties and took off my panties that I had worn to dinner. She helped me on with the black panties.

She gently guided me to the bed and laid me down. She stood over me and started masturbating the cock like a man would. She added some lubricant and continued jacking off. She reached some lubricant to my crotchless panties and placed a copious amount on my boi pussy. She held my legs up and pushed her cock slowly into my panty opening. I felt the dildo gently touch my boi pussy opening. She held it with her hand and moved my legs to her shoulders. As she inserted the tip, I shuddered. I moaned in excitement. She pushed tenderly in a little at the time. She pulled back and thrust back in. She was now fucking my boi-girl pussy in earnest. She gained a slow steady motion plowing deeper and deeper each time. The pain gave way to unbelievable pleasure as everything below my waist was on fire.

I screamed, "Fuck me with your big cock. Fuck me harder. Fuck me faster. Make me a bitch. I am your sissy bitch. Please fuck my pussy."

My cock was now as hard as it had ever been. The pressure on my prostate was exhilarating. And then... My little hard cock erupted the largest cum explosion I had ever experienced. The cum came up and shot up in the air landing back all over my panties, stomach, bra and face. Spurt after spurt erupted like a volcano spewing hot lava. As Jessica pounded my boi pussy, some of it hit her in the face also. She kept pounding my boi cunt until I could take no more.

She stopped, pulled off the leather harness and cock, and then mounted my face with her steaming pussy. I felt engulfed. The afterglow of my orgasm was short lived as she fucked my face, mouth and tongue with her aroused girl pussy. She bucked herself to a huge orgasm, but did not stop. She paused as she squeezed my head with her thighs. She shuddered and paused and then began fucking me again. She came again. She paused and breathed heavily. Then she began fucking my face again. She went on this way until I thought I would smother. I managed to push her ass up occasionally to take a breath. With her last orgasm, she bucked forward and collapsed on me. Her pussy was flooding my face and the sheets. She had had a super girl cum each time she climaxed. My whole body was wet. My wig was wet. My face was drenched. I held her hips and kissed her inner thighs. We lay this way for an undetermined amount of time.

Then, she rose back up and fucked me with her pussy again just in case she needed another orgasm. She came again on my face. She relaxed and backed off me. She thrust her pussy back onto my hardening cock. She humped my cock until I shot off into her. She did not cum, but she was satisfied getting me off inside her.

We fell over in bed and slept. When I awoke the next morning, I was a complete mess. I had been ridden hard. My wig was possibly ruined. I was wearing crotchless panties, thigh highs, bullet bra and my ass was sore. It was the best hurt I had felt so far. Jessica was still in her leather bra, fishnet hose and boots. We slept until almost noon. Finally we got up and showered. Jessica told me how much she enjoyed fucking a true little virgin.

jealouscuck
jealouscuck
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6 Comments
bggb29bggb29about 4 years ago

What a great gal

AnonymousAnonymousabout 7 years ago
Double Date

I know what will happen next. Femme hubby and dominant wife will double date two " real men" . Brianna will become a complete woman and Jessica will adore being with a alpha male. Ms Peggy

AnonymousAnonymousover 7 years ago
More to Cum?

I hope she gets you to finally take a real cock up that sweet bum

DianeRedfernDianeRedfernover 7 years ago
Loving and exciting

Excellent unfolding - very talented writing. I enjoyed the pacing, the flow and most of all the dildo sex. Got me so wet all over I had to read it twice.

xoxo,

Di

AnonymousAnonymousover 7 years ago
Erotic!

A wonderful addition to the series. Oh to have that kind of partner!

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