Helping My Wife

I am a 40 year old man who has been married to my beautiful wife for twenty years. Like many Americans, inflation has taken it's toll on our finances. I have been incredibly stressed lately trying to make ends meet, especially with a daughter, Brianna, getting ready for college. It has effected my sex drive, and I can feel my wife getting frustrated. About 6 months ago my wife took a job as a secretary for a big law firm in town. I must admit we need the extra income, but I am also a bit jealous seeing her dressed up everyday going into an office full of horny lawyers.

A few weeks ago my wife came home all excited.

"My boss and his partner are sending me and the partner's secretary Jessica out of town next month to meet a couple of potential clients. If they decide to use our firm we will each get a $20,000 bonus."

"That's great." I said. "We can sure use the money, but I am not sure I am happy with you going away for the weekend to entertain some guys."

"Don't be silly, I'll be sharing a room with Jessica, I don't think there will be any fooling around happening. Not that I would mind, it's not like you pay any attention to me lately. The other night I got all dressed up, put on my hottest slutty lipstick, played with your cock, and nothing happened. If I didn't know better I would think you were gay."

"I'm sorry honey, I had a bad day at the office. I still think you are incredibly sexy, and I get jealous thinking of all those men you work with at the firm."

"Don't be stupid",my wife said. "Most of the men in the firm are married, and we have serious sexual harrassment rules. But to be honest I don't think I would mind if someone hit on me or at least squeezed my tits or grabbed my pussy. A woman has needs you know. Why should our 18 year old daughter being the only one getting laid?"

Again I apologized and promised to be more attentive. I did understand her frustration, and by the tone of her voice I was wondering if I was driving her into having an affair, and just maybe that was getting me excited.

The next day my wife came home with a few bags and in a very good mood.

I asked. "You seem in a good mood, what's in the bags?"

"My boss gave me money to go shopping for my little trip. He told me to buy a couple of sexy outfits,do you want to see?"

She then unpacked the bags. There were a few pairs of sexy panties and matching bras. Some stockings, a garter belt, a couple of short skirts and dresses. "This should help me get that $20,000 bonus."

"Don't you think that's a little slutty?" I asked.

"I don't think so, you should see what Jessica bought. Don't tell me you are getting jealous again? This is what women are wearing on weekend getaways these days, just ask our Brianna."

Again, I didn't know if I were jealous or excited. But it was nice to see my wife happy.

The next few days as soon as my wife came home from work Brianna would encourage her to try on one of her outfits. Then she would compliment her. "Wow mom you are certainly hot. Dad, all my friends think mom is a MILF. If I look like that when I am her age I would be getting laid all the time."

"That's quite enough young lady." My wife said. Then she added. "Do your friends really think I am hot? Should I wear red or pink lipstick with this outfit?"

"I don't know." My daughter said. "Why don't you ask dad?"

I have always had a bit of a lipstick fetish. I loved when my wife would put on lipstick to suck my cock, but I chose not to answer. My wife and daughter were having too much fun teasing me.

All went well for the next week or so. My wife came home in a good mood, her and Brianna would put on fashion shows. One night Brianna had my wife pose for some pictures. Then she would send them to her friends. Her phone went wild with text responses from her classmates. All the guys, and some of the girls, commented on how hot my wife looked. Brianna would whisper in my wife's ear about which friends had big cocks. Finally my wife said. "That's enough, you are making me horny, I might need to borrow your vibrator tonight."

Everything changed the next day. My wife got a phone call from Jessica. She had a family emergency and would not be able to go away next weekend. My wife got very upset. "There is no way my boss will let me go alone on this trip. I guess he could send one of the partners, but I was looking forward to going with you Jessica."

"I was looking forward to spending time with you, but this emergency came up. Before we tell the boss I have another idea. Let's go out after work tomorrow and I will run an idea by you."

The next day my wife calls and tells me she is going out with Jessica and will be home a little late. So after work my wife and Jessica go back to Jessica's apartment. They have a couple of drinks and finally my wife asks. "What is this plan that you have?"

Jessica finishes her drink and says. "I've been thinking. You're husband and me are about the same size. On more than one occassion you said you thought he was a little effeminate. I've met him a couple of times and I think he definitely has some feminine qualities. Maybe you can convince him to dress up as a women for the weekend. I just bought these new clothes. Why don't you take them home, run the idea past your husband and see what he has to say. Use your charm, figure out a way to get him to agree and I will come over tomorrow and help you turn him into an attractive woman. The men we are meeting that weekend don't know who I am, your husband can become Jessica."

My wife says. "Maybe it's the alcohol, but that's not a terrible idea. I will go home and run it past my husband."

My wife comes home from Jessica's, kisses me and says. "Honey we need to talk."

I am a little worried, but she insures me that everything is ok.

"i just had a long talk with Jessica. She came up with this idea. She just bought all these sexy outfits for next weekend, and since she can't go and you and her are the same size, well maybe you could wear them and go as Jessica. Remember that halloween when you dressed as a woman? You didn't look half bad, and I think with a little practice you could pass. I think you can more than pass, I think you would make a hot looking woman."

I really didn't know what to say, and then she continued. "You know how much I was looking forward to the weekend. We will be staying in a really nice hotel, the firm will be paying for everything, and we could use the $20,000 bonus. Please, Please, Please."

I thought for a moment and said. "I don't know if you could pull this off. Dressing for a Halloween party is one thing, but going out and trying to fool your potential clients is something else."

'I will tell you what." She said. "Jessica will come by tomorrow night. We will dress you up, try some of her new outfits, put on some makeup and see how it goes. If you are not comfortable you don't have to do this."

Then she said the magic words. "If you do this there will be a lipstick blowjob in your future."

I was hooked and agreed. My wife called Jessica and made plans for her to come over the next day.

Both my wife and Jessica took the next day off. They made up some excuse to their bosses about needing to do some last minute shopping for the weekend. Jessica came over late morning and thanked me for doing this. "If you can pull this off you will save my job."

My wife took me and Jessica into the bedroom. "Let's get started." She said. "Take off those male clothes."

There I was completely naked in front of two attractive women. Jessica said that I need to shave my body, but my wife suggested we just start by putting on her clothes. "We can worry about shaving him later."

First came a pair of silky pink panties. "Try these on." My wife said. I put them on. They actually felt really good and I started to get excited.

"Look." Jessica said. "Is that a bulge in those panties? Is that some pre cum. I think your husband is enjoying this."

My wife agrees and asks. "How do they feel honey, looks like we may have to buy a few more pair. I haven't seen your dick that hard in a long time."

I admitted they felt good, then Jessica said. "Let's try on this matching bra."

She puts the bra on me and stuffs something inside to make it look like I have boobs. Then they help me put on stockings and asked me how they felt. I admitted they felt nice and I was got more excited when Jessica said, "Imagine how good they will feel once we shave you legs."

Next came the sexy dress. Then they sat me down and started with my makeup. Some blush and powders. My wife said. "You have such nice blue eyes, let's make them sexier. Eyeliner, mascara, and eye shadow. Then some pink lipstick and lipgloss. Jessica commented. "Now, that's what I call hot cocksucking lips."

I didn't know how to feel about that comment, but when she put a blonde wig on my head and told me to look in the mirror I couldn't believe what I saw. I really did look like an attractive woman.

The women decided that we should call it a day. My wife told Jessica. "I will shave his legs and pussy tonight and we will continue tomorrow. We still need to work on walking in heels, and I think he, I mean she, needs a trip to the nail salon for a nice manicure."

Jessica agrees and heads on home. I guess we lost all sense of time, because about 5 minutes after Jessica left our daughter came home with a couple of friends. She introduced us to Lacey and Jim. "We are going to my room to study, can my friends stay for dinner?"

My wife says. "Of course, is 6 o'clock ok?" Then she introduces me. "This is my friend Jessica, she works with me at the law firm. Have fun studying, see you at 6."

My daughter and her friends head to her room, and a few minutes later my wife and I go to our bedroom.

"I do believe you just passed your first test as a woman. I don't think our own daughter recognized you. Now, get undressed and take a shower. I will shave you before you put your male clothes back on."

I took a quick shower than my wife began to shave all my body hair. It felt very weird when she shaved my pubic hairs. She kept thanking me for doing this favor I didn't even mind when she referred to my genitals as my pussy. I started putting my male clothes on when she stopped me. "Put on these panties. I think you should get use to wearing them. Besides, I can tell you definitely like them."

At 6 o'clock my wife calls Brianna and her friends, and 5 of us sit at the table. Our daughter asked if Jessica was joining us, but my wife said that Jessica had left. Dinner was pleasant, lots of small talk about school and work. After dinner Brianna's friends left and me, my wife, and Brianna sat around the livingroom. Brianna said. "My friend Jim thought that Jessica was hot, is she married?"

"No." My wife said. "She has a boyfriend."

Then Brianna smiled. "I know that you were Jessica dad, you make an attractive woman. But you definitely fooled Lacey, and Jim did think you were hot."

I tried to deny it, but my wife finally admitted that I was Jessica, and then proceeded to tell Brianna the entire story of the weekend with clients and how Jessica had to cancel, but thought I could pass as a woman and go in her place.

Brianna agreed that I could pass as a woman, and she was willing to help in any way she could. "Thank you." My wife said. "Maybe you can help me and the real Jessica over the next few days. Your dad still needs help with a few things, like walking in heels, maybe doing his makeup, and anything else you can think of."

That night when me and my wife were getting ready for bed she gave me a big kiss and thanked me again for taking Jessica's place for the following weekend. I was hoping for sex that night, but when I started getting frisky my wife stopped me by saying, "I love you honey, but I am not sure I could have sex with someone wearing panties. But I didn't forget that there will be a lipstick blowjob on your future."

The next afternoon Brianna came home from school to get started, but my wife wasn't home yet. I tried to convince her to wait, but she was so anxious I agreed. I certainly was not about to strip naked alone with my daughter, so she decided to work on my makeup. She taught me how to apply eye makeup and complimented me on how pretty and feminine they looked. She told me all her secrets about lipstick. What she wears to look pretty, what she wears to look sexy, what she wears to pick up guys, what she wears to look slutty.

"That might be too much information, but thanks for the tips."

Just then my wife and Jessica walk in. My wife says,"What a great job you have done with your makeup, you are looking more and more like an attractive woman."

I give Brianna all of the credit, but she says that I did 90% by myself. "She didn't teach you about flirting or picking up guys, did she?" My wife asks.

"Not really." Brianna smiles. "I just told him what lipstick I wear if I want to pick up a guy."

Jessica suggests that since my makeup is already done maybe I should get dressed and the four of us should go to the mall. "We can do some last minute shopping, grab a bite, have her practice being female in public. Maybe me and her can go get that manicure. I need my boss to think I will be seeing the potential clients this weekend. He always comments when I get my nails done."

So the girls proceed to help my get dressed. This time it's a matching black panties and bra. I have a little problem putting on the bra, but they say we will work on that later. I put the stockings on by myself. I can't believe how amazing the panties and stockings feeling on my shaved legs and pussy. The girls all notice my erection in my panties and I get a little embarrassed. My wife says, "You are really enjoying this, maybe you should dress up all the time."

Me,my wife,Brianna,and Jessica drive to the mall. First stop Victoria Secret. Jessica tells me to go in and buy some panties because I got pre cum stains on a couple of pairs. "Better buy at least six pairs. Make sure you ask a sales woman for help."

I go in and buy six assorted colors, much to the delight of the three girls. Next stop the makeup store. I am told to pick out a couple of lipsticks. I go in and pick a red and a shiny pink. The girls then decide to go to dinner and leave me in the mall alone for an hour, then meet them at the nail salon. I wander around the mall. I find myself window shopping at women's clothing store. A couple of good looking young men are definitely looking me over, and I am definitely getting a little turned on. One 20 something year old tells me I am hot and asks for my phone number. A few minutes later I meet the girls at the nail salon. Jessica and I go in while my wife and daughter decide to do some last minute shopping. Jessica and I make small talk while two women were soaking our hands. Jessica thanks me a few dozen times more and tells me to have fun over the weekend. "To be honest, I wish I were going, but I hope you and your wife have an amazing time."

We meet my wife and daughter a few minutes later and drive home. Brianna starts telling us that her friend Jim was talking about me at school. "He really has the hots for you and wants to fuck you. I hear he has a nice cock."

My wife says. "Brianna when did you start talking like that? Let's keep the conversation a little less slutty." Then she adds. "Does he really have a big cock?" Everyone has a good laugh. We get home and Jessica says. "Same time tomorrow. Have a good night."

Again the next day Brianna arrives before my wife and Jessica. She has me do my makeup by myself, complimenting me on how well I am doing. "If I didn't know better I would think you have been wearing makeup, or at least lipstick, your whole life. Have you?" Then her conversation becomes more X rated. "I think you should suck Jim's cock. My friend who have given him blowjobs all say he has a big cock. I am not really into him, but would love to see you suck his cock to see how big it really is."

"Please Brianna, but I don't think we should be having these conversations." But secretly I was getting excited, and I think Brianna knew it and kept the sexual conversation going. "Wow, my pussy is getting wet thinking of watching you suck Jim's cock. Is your pussy getting wet too. Would you like to borrow my vibrator?"

Fortunately, just then my wife and Jessica walk in and Brianna stops talking. My wife is so impressed that I did all the makeup, and like Brianna questions if I had done this before. The girls decide to dress me up in another of the sexy outfits that Jessica had bought. Putting on stockings is getting easier, as is putting on a sexy pink bra.

The girls also decide to sit around for a few hours giving me feminine tips, and maybe later going to some bar and have me experience what it's like to have men hit on you. They have me practice a little more walking in heels, work on posture, innocent flirting, how to cross my legs, etc. With every little thing I feel more confident that I can pull this off.

About 9 pm the girls decide we should go out to a local bar. Me, my wife and Brianna drive in one car, while Jessica drives alone in her car. "Maybe I'll get lucky and meet someone." She said.

We get to the bar. More cars than usual for a week night. I am about to get out of the car when my wife says. "Did you forget something dear?"

"Oh yea, I forgot to freshen my lipstick." "Good girl",my wife say as I apply some lipgloss.

We go inside. There are more men than woman, but after the four of us walk in the numbers became a little closer. Sitting at the bar were Brianna's friends Lacey and Jim. My wife asks Brianna. "Did you tell Jim that your father was going to be here?"

"I may have told him Jessica was going to be here." Brianna grins as she walks over to meet her friends..

The three of us find a table and order drinks while my wife and Jessica check out the men in the bar. "Too many young men here tonight",my wife says.

"Nothing wrong with that", answers Jessica.

We are about half way thru our drink when Brianna comes over to our table. " Dad, Jim offered me $20 if I could get you to dance with him. He's a little on the shy side, but he is kind of cute. Please dad."

My wife says,"Brianna, don't call her dad. Go ahead honey, dance with Jim. He is kind of cute." Brianna takes my hand and walks me over to the bar. "You remember my friends Lacey and Jim?"

"Yes I do. Jim did you want to dance?"

Jim nervously said. "Yes, I'll go to the juke box and pick out a slow song."

So I take his hand and we walk over to the juke box. Moments later a slow song starts playing. We head to the dance floor where there are a few other couples dancing. I can't believe how turned on I am having a cute young man holding me close on the dance floor. I whisper in his ear that he's a very good dancer and he smiles. I don't understand what is happening to me, but all of a sudden I want Jim to kiss me. The song is over. We walk back to the bar. Jim thanks me for the dance and we make small talk. Now I am thinking to myself, it's now or never, and I give him a kiss. He kisses me back and our tongues meet. I am nervous, hoping he doesn't notice the bulge in my panties. I certainly noticed the bulge in his pants.

"Thank you for the dance." I say. "But we have an early day at work tomorrow. Please ask Brianna for my phone number and give me a call." I kiss him goodbye, brush my hand against his cock and go back to our table as my wife and Jessica stare at me with their mouths wide open.

We go to the car and drive home. Brianna says,"it looks like dad, I mean Jessica has a boyfriend."

"She does have a glow about her, should I be jealous?" My wife asks.

When we get home my wife says,"We need to talk. Clearly dressing up as an attractive woman has changed our marriage. I don't think it's a bad thing. Your relationship with our daughter has never been better, but I have needs, and I can't see us having sex again. But look at the fun we can have going shopping, going out and picking up hot guys. I think our marriage will be better than ever. Let's sleep on it, and talk tomorrow." Then she gave me a big hug and said. "I love you."