A Halloween to Remember Ch. 02

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The morning after the Halloween party, we woke up as usual. I felt a little different under the covers until I remembered what had happened after we made love the night before. We had showered and then I picked out two pair of sexy panties. One for Jeff and one for me. I looked over at him as he started waking up. Jeff had been at home from work for a while and we had no plans for the day. When he roused enough, I slipped over to him and cuddled. I had him turn on his side and I played the big spoon to his little spoon. It just sort of worked out that way. I was not making a statement, but afterwards I did grasp the significance.

The girls had initiated the costumes for the party, but the guys had gone along. After the party, I had led Jeff into our first ‘lesbian’ sexual encounter. I purposely did not let him penetrate my pussy with his cock instead bringing him off with my hand. Now I began rubbing his pantied cock until he was hard again.

I did not want to lose the theme from the party. Sonia had intrigued me with her stories of how Keith had taken to the start of their feminization fetish. I had the hots very badly for duplicating this with my own husband. The first step had been a success. I wanted to get with Sonia about what their after party had been like, but I was not ready to share any details about Jeff and me just yet. I would let her bring the subject up and not quiz her too closely. Otherwise, I would feel obligated to report our bedroom activities also.

I had thought this through. Since Jeff had gone along with the costume for the party, I was feeling a certain anticipation for the expansion of my plan. After the party and after making love, putting him into panties for bedtime was the sure sign that he was not averse to the idea. I did not necessarily expect him to embrace it to begin with. At that point my only goal was to re-enforce the new pleasure and hopefully get him comfortable with the idea.

When it was time to arise and have our coffee, I made sure to be the first one to speak.

“God, Honey, last night was fantastic. I don’t know what came over me. I guess the anticipation and planning for the party got me going. When all you guys agreed, we thought it was so sweet of you to go along with our kinky idea. Seeing what a big hit you all were made us so pleased that Beth had thought of it. Although I must admit that Bart was not very believable. I thought you were the prettiest. Keith looked good, but you are shorter and the stilettos looked more natural on you. Did you enjoy it?”

He seemed to be looking for some kind of sign. After all, waking up in your wife’s panties is not exactly what you would brag about to your buddies. I was hanging on his response…

“Yeah, it turned out okay. I expected some of the other guys to really get personal about it, but everyone seemed to enjoy the joke.”

“It was sweet,” I cooed. “I had not idea it would turn me on so much to see how good you all looked made up. I never made it with a girl before. Much less a gorgeous one.”

I jabbed him and ran my fingers over his cock now tenting the front of the pink panties. Jeff was not big by any means, but his cock did get hard. Also, he was a heavy cummer. When I blasted him with my girl cum, I was hoping that it did not turn him off. I hugged him again and suggested that we get some coffee and go back to bed. He started going toward the bathroom. I had to act quickly.

“Oh, and Honey, would you leave the panties on? I want to re-live our wild sex night while we have our coffee. Go to the bathroom and I will get our coffee.”

As I poured the coffee, I was excited to see if he would come out with my panties on. He did indeed leave the panties on per my request. I put our coffee on the night stands and again told him how sexy he looked wearing my panties. It must have been the ‘manly morning after masculinity syndrome’ because he said, “Sandra, the costume party is over”. He said it but without firm conviction. I was determined to explore the fetish mainly because Sonia had been so enthusiastic about Keith being totally into it now.

“Oh, but Honey, I had such a good time last night. I mean the party was fun, but our lovemaking afterward was off the charts. And you look so sexy all cleaned up and smooth. I bet the guys who propositioned you last night in jest were a little turned on by the, uh, dark intrigue of anonymous prostitutes being so near to them.”

Jeff was in a casual mood, but still showed some reluctance to engage in the conversation. I wanted to explore this a little further, but not press it enough to make him uncomfortable. If this was not something that appealed to him, we would drop the subject and I would have memories of the party and the wonderful sex we had afterward.

He did answer. “It was so different bahis firmaları and you girls seemed to get a kick out of it. Bart looked sort of out of place. I mean he shaved his mustache and still looked like a bulky guy.”

We laughed and began to compare the outfits and makeup of the other guys. I asked him about the razzing he got from the other men who were dressed more traditionally. Jeff thought that some of the guys’ costumes looked ridiculous. He said that a couple of them were much less believable than the hookers except for Bart. I reminded him that even though it was a stretch for Bart to look feminine, he still was willing to go along with the theme because Beth really wanted to join in the fun with the rest of us.

“Yeah, Sandra, but that does not explain the ‘after party’ we had. Don’t you think that was a little over the top?”

“Over the top? Is great sex over the top?”

“You know what I mean. Dressing for the party was one thing, but dressing for bed makes me feel uncomfortable.”

“How so?”

“I don’t want people to think of me in that way.”

“What people, Jeff.”

“If anyone knew about this, I would be humiliated.”

I could see his concern.

“Jeff, the party was a costume party. You said yourself that some of the other guys looked terrible in their costumes. You guys were gorgeous. Bart did not ruin anyone else’s costume. He complied with his wife’s wishes. He gets an A+ for that just like the rest of you.”

“Oh, I didn’t mean it that way,” he objected.

“Jeff, I had a great time last night. If it made you feel uncomfortable, we should drop it and believe me, I will not publish on the internet how much I enjoyed my husband pleasing me in bed.”

He blushed and looked a little guilty for trying to put up a defense after the fact.

I continued, “But anyway, like I said, it was so fun. And I won’t put you in that predicament again if you feel all threatened.”

“Oh, Sandra, I am sorry to come across that way. Yeah, I had a good time last night also. You were so…, uh, so, horny. Why did that turn you on so much, really?”

“Really? I don’t know for sure. The thought of you guys being so great about it. And no one freaked out. That is as old a theme as, well,…, I guess prostitution itself. Many highly successful screen actors have taken on the role of a woman. It shows their range of talent. For a man to be seen as a real woman is about the ultimate in acting skills. Take Dustin Hoffman, Jack Lemmon, Tony Curtis, Tom Hanks. That is just to name a few. And I’ll bet that there was probably a certain sexual thrill over and above their satisfaction of a great performance.”

“So,” he asked, “You’re saying that men get a sexual thrill out of dressing like a woman?”

Boom. Magic question. How I handled this answer would be the determining factor of whether Jeff would enjoy this as much as apparently Keith does.

“Don’t know. I must ask you. Did you get a sexual thrill out of dressing as a sexy prostitute?”

He paused, not sure how to answer.


“Uh well, now that you mention it, I guess, yeah, in a weird way. I can’t explain it though. I was like the first time you masturbated growing up. It was fun, but you were supposed to feel guilty about it.”

I giggled, “Yes, we were all made to feel guilty about anything sexual. It was our parent’s way and the way of religion to protect us from things that we were not mature enough to handle properly. And that was good in a way. Not so good in other ways. We carry through those feelings into adulthood. I am not saying that we should disregard our moral upbringing, just that when married adults engage in mutually satisfying actions, it is the height of marital bliss.”

“That sounds right. I guess when you put it that way it makes sense. And yes, you were a ball of fire last night. I have never seen you so turned on. It just caught me by surprise that you were so passionate. I have heard of women squirting during orgasm, but you have never done that before.”

“I hope that did not turn you off, Honey.”

“No actually, it seems to be a popular topic in porn. I mean, from what I have heard and read, that fetish turns men on. I know when it happened, it caught me by surprise, but when I realized what was happening, it was a real turn on. Even though I did not cause it, it was still sexy.”

“The hell, you didn’t cause it, Girlfriend. Who else was there eating my pussy? But on second thought, it was your new alter ego. And I am beginning to fall in love with her too.”

I sensed that it was time to move a little further. I was going to wait and let the smoke die down before I suggested doing anything again, but thought we were making progress, so I asked.

“Well, I can tell you it really rang my kaçak iddaa bell. After you shower, will you let me fit you in another clean pair of panties?”

“Uh, to wear today?”

“Sure, why not? I want to keep the feeling alive for the rest of the weekend. I might even have a little something in mind for my ‘sexy hooker’ tonight.”

He showered. I was waiting for the water to stop and gave him a few seconds. He did not go into the bath with any briefs. After I was sure he was finished drying, I entered the bathroom and took him by the hand. I led him to my lingerie drawer and said, “Pick your color, Girlfriend. Or how about we call you Gina, if we play this way again?”

My playful and accommodating nature must have intrigued him for he reached in and selected a pretty peach colored bikini panty. He put them on. I felt all around the thin material of the panty and gave his hardening cock a little pat just for good measure. On a whim, I opened his underwear drawer and put on a pair of his cotton ‘tightie whities’.

“See how boring these are, Jeff? Aren’t mine so much prettier?”

He smiled at this. I walked around a little and then took them off. I tossed them into the garbage can in the corner of the room. I then selected a hot pink thong and stretched it over my glistening pussy. I gave him a big kiss. We both pulled on a pair of shorts. Jeff put on a tee shirt and so did I. I left off my bra. I suggested that we go shopping for groceries and some wine. During our shopping trip, I frequently rubbed the outside of his shorts making sure to slide the material over the softer material of his panties. I made sure to rub my breasts against his arm every chance I got and my nipples were poking holes in my shirt. I had plenty of stares directed to my poking nipples. I noticed both men and women eyeballing my breasts. In fact, I noticed several women who seemed to enjoy the sight. Naturally some of the old biddies gave me the disgusted look that always seems to come from unattractive people.

Back at home, I cooked a nice dinner and served several glasses of wine. I announced that I was going to get a shower. Jeff was to put the food and dishes up and join me in the bedroom later. When he came into the bedroom, I was not quite ready, so I asked him to watch TV for about ten minutes. I put on my old robe and some ugly house shoes and told him that he could shower next. While he was in the shower, I removed the robe and put my feet into my stilettos. I was wearing a white thong, white garter belt, suntan stockings and red high heels. My DD’s were barely contained in a half demi-bra. I had put on a sheer duster that hid absolutely nothing but added to the overall femininity of my outfit. I had also applied my version of hooker makeup that suggested ‘hot female’ but did not scream ‘hooker’. I thought a little less garish and a little more doll face.

He came out of the shower to find me standing at the foot of our bed rubbing my pussy through my thong. I led him to the bed and propped him up with a couple of pillows. I put on some lively music and began dancing and swaying to the tunes. I used all my dancer moves and was as sexually suggestive as I could be. His cock was standing at attention. I touched him little by little, making sure to avoid his cock each time. I let my hair fall over his chest and then legs, but never let it touch his cock.

I took his hand and sucked his fingers into my red painted lips, then move them to my pussy. I pulled my thong aside and had him bury his finger into my dripping pussy. I moved his finger back up to his mouth and had him suck my juice. His cock was hard and starting to ooze precum from the tip. I placed his finger into the gooey liquid and then guided it back to his lips. As he opened his lips, I held his finger to the tip of his tongue. Then back down to his cock and this time I placed his wet finger onto my own tongue. We shared his precum for a while and then I took his whole cock into my mouth and didn’t stop until I had his entire length in me. The tip did not reach my throat, but the fullness was pleasant. I sucked him, making sure that he did not cum.

I got up and gave his cock a few strokes and then danced away again. I seductively removed my thong and wrapped his cock with it. I dabbed the material into his stream of precum. I pulled his dripping cockhead back into my mouth and coated my tongue with his secretions. I then moved up and shared the bounty with him. I got up on the bed and mounted his face with my naked pussy. There is no other way to describe it. I fucked his face. I moved my pussy all over his mouth, nose and face. I wanted to drown him in my juices. I came on his face twice. Each time after I orgasmed, I found new energy and fucked him harder. I was screaming, “Eat my cunt, Bitch. Fuck my pussy with your kaçak bahis face.”

As I orgasmed the final time, I again squirted a torrent of girl cum all over his face. I dismounted and stood beside the bed. I moved his hands to his cock and showed him how to masturbate. I stepped back and shouted, “Drench those panties with your cum, Girl.”

He didn’t last long. He shot ropes of cum upward. One shot made it up to his chin. The rest was spread out from his face to his stomach. Even though he is a heavy cummer, I was surprised at the volume of his ejaculate. As some of it started running off his body, I quickly sucked it up and snowballed the cum into his mouth. The rest of it, I guided his hands to the pools and had him scoop the cum up and suck it off his fingers. I shared it with him, taking care to make sure that he ate most of it himself.

We seemed to be on a similar path to Sonia and Keith. I don’t think I would ever have imagined that Jeff would be turned on by dressing as a woman. The Halloween party had been a coming out party of sorts for Keith. Sonia’s stories about their bedroom activities had certainly excited me and now it appeared that Jeff was becoming more comfortable with feminization. The new elements in our lovemaking were, I hoped going to be of lasting enjoyment. Already we had experienced squirting, crossdressing and cum eating. Jeff had never eaten his cum from my pussy, but that was the part I was keeping separate. I did not intend to let him enter me and have a traditional experience. I wanted to keep him in the feminine role and females do not have a cock. For now, letting him masturbate in panties was going to be the type of sex he would have to get used to in order to cum.

I did not know exactly how we were going to expand the fetish, but I knew there would be an almost endless supply of role-playing ideas. I began to mull over some playful scenarios that we could use within the confines of our home. I was not looking to dominate him in a bondage sort of way, just lead him into a more imaginative role for himself. To make this work I believed that I would have to take the lead initially for our sex play. Later I would have him move the needle himself, but in fact I would be the one to propel the development. I just hoped that he would enjoy it as much as Keith seemed to.

When I was alone with Sonia again, I did not bring up the topic. Finally, she asked if we enjoyed the party and how Jeff was afterward. I did not want to put our business out there, so I just indicated that we really enjoyed the experience and that Jeff had a newfound respect for what we girls go through to look nice.

“Did you guys do anything when you got home?” she finally asked.

“What do you mean? Like take off the makeup?” I asked.

“No silly, sex?”

“Oh,” I declared innocently. “Yes, we did have sex after the party. You guys?”

“God, yes. Keith was so turned on with getting to dress up completely and wear the makeup, shoes and of course the sexy lingerie. We had what I would only call the most passionate love session of our entire marriage. I must have created a monster when I rubbed his cock with my panties. We can’t get enough of each other.”

“Has the fetish worn off yet?” I asked.

“No. It is more and more elaborate. I have been buying him panties, garter belts and stockings ever since the party. I dress him completely before sex. I mean makeup, wig, his own high heels and matching bras. He has quite a collection of bras now. We buy different cup sizes for him to wear according to how sexy we want him to be. So far, we only stuff the bras with pantyhose, but I am going to order him some breastforms. This is so exciting. I mean, I am trying not to gush, but this is amazing. I hope we are talking in confidence here. I don’t want this to get out to the group. I probably shouldn’t have told you in the first place, but the party just got me all revved up.”

I was revved up also, but I was going to slow play my comments.

“Now that you mention it, Sonia, Jeff did seem turned on that night. I first thought that the party and the alcohol had lowered his inhibitions, but when I asked him to leave the lingerie on in bed, he seemed more than willing to participate.”

“Did he fuck you all night, Girl?”

“Not quite, but he brought me to several crashing orgasms, but not with his cock. We made lesbian love, you know, oral?”

“That’s all?”

“Well, I used one of your tricks and had him jack off into the panties.”

“I bet that made a mess on some sexy panties.”

We giggled.

“What about since then?”

I didn’t want to spill the entire pot, so I just said, “I had him jack off with the panties a few nights ago and he came all over himself. I had him eat it. We shared some of it, but he ate most of it.”

“No? Oh, my, god, Sandra. He ate his cum?”

“Is that a big deal?”

“How sexy. I am going to get Keith to do this. I thought we were the kinky ones, but your husband actually ate his own cum.”

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