HOW ROBERT BECAME SISSY ROBERTA hottest Crossdre
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A Surprising Evening At Robert And Wilma's free porn video
I waited nervously after ringing the doorbell.
Within seconds I heard footsteps approaching then the knob turned, the door opened and Wilma was smiling at me as she invited me in.
Wilma was wrapped in a fluffy white robe, unusual for this time of year, but as she took it off, she explained that she was wearing it only in case it was not me at the door.
Now I could see why. She was wearing a very small, translucent red Teddy through which I could see her erect nipples and the cleft of her shaved pussy.
After a hug and a peck for a kiss, she said "Robert is waiting for you on the patio, but wants you to undress here before joining him" As she reached for my belt, she said "Here, let me help."
"Fine with me", I replied, "and let me comment that you look simply stunning tonight, Wilma."
"Why, thank you, Larry, I'm glad you think so. I do want to look good for my two favorite men."
"Good enough to eat", I said with a chuckle, "and I know how good you taste."
"Quit that, Larry. I'm already wet enough as it is. All Robert has talked about this evening is your visit tonight and it's gotten me as hot as I can remember being."
As the last of my clothes hit the floor, Wilma moved to my side, took my cock in her hand and began to slowly stroke me up and down.
"Oh, goody!", she exclaimed, "you're already getting hard. Robert will like that. Come on, let's go", Wilma said excitedly as she started leading me to the patio door by my cock.
I had met Robert and Wilma at a very nice, upscale cocktail lounge about three years ago. A typical middle age couple out for some relaxation was my first thought of them and for the next several months had no reason to think otherwise.
Then something happened ... doesn't it always ... that changed my mind and made me wonder.
One weekend evening, there had been a new and very talented piano player booked for the evening's entertainment and the floor always had at least three couples dancing to some very smooth music.
Although I'm not really much into dancing, I've been told that I'm pretty good at it, but, being alone, was content to sip my drink, have idle short conversations with the bartender and watch the couples enjoying the music.
After about an hour, Robert came up to the bar to refresh his and Wilma's drink and, as he was about to return to their table, invited me to join them.
As we joined Wilma, I took my first notice that she was dressed simply, but elegantly in an off white silk blouse and long flowing madras print skirt. The image of femininity and class.
As the drinks flowed, thanks to Robert, we talked and got to know each other far better than we had over the previous two years of occasionally seeing each other at the club. He and Wilma danced when one of their favorites was played and, all in all, we had a very enjoyable time ... at least I did.
Then Robert invited me to dance with Wilma, pleading that it couldn't be much fun being the only lone man in a group of couples and that Wilma would enjoy the "change of scenery".
OK ... I can do that ... and we did.
Surprisingly, Wilma blushed as I took her hand and asked her to dance when the piano player began one of MY favorite tunes. I noted her reaction, but didn't make too much of it ... just a new experience for her, I thought.
As I held her to dance, I instantly noted that she wasn't wearing a bra under that demure silk blouse and if you don't think that got my attention, think again.
Wilma was an accomplished dancer and easily followed me smoothly around the dance floor. I was actually enjoying dancing with her which is something of a rarity for me.
As we returned to our seats with Robert, he smiled and said, "There. That wasn't so bad, was it?"
I didn't know whether he was talking to me or to Wilma, but noticed that she gave him a small shake of her head and blushed.
Now, I was definitely curious, but said nothing. I just took my seat, finished my drink and collected their glasses before returning to the bar for refills.
As I waited for the bartender to fill my order, I could see that Robert and Wilma were concentrating on their conversation. Heads close together, they appeared to be discussing something serious, but sat back with smiles when I again approached with fresh drinks.
The music really was a cut above what we normally got from the local talent pool and we all stayed far longer than usual and, of course, drank far more than usual as well.
I danced several more with Wilma and enjoyed not only her dancing skills, but the feel of this attractive woman in my arms.
She appeared to relax more with each dance and was soon leaning into me during the very slow songs.
But, all things must eventually come to an end and suddenly, and surprisingly, the bartender was giving last call. Where had the time gone?
As we stood up to leave, Robert stumbled and nearly fell over. I grabbed him and sat him down again, asking if he was alright. It was obvious that he wasn't.
Robert hadn't danced much after I started dancing with Wilma and it had escaped me just how many drinks he had put away. He was not drunk, but was feeling no pain and was in a happy, frivolous mood.
A bit concerned, I asked Wilma if she was sober enough to drive them home and she responded that she thought she was.
I didn't want to take the chance on either of them getting hurt or running afoul of the local gendarmes, so I told them that I would drive them home in their car and either have a friend pick me up or take a taxi back for my car.
Since they drove a Lincoln, there was plenty of room in the front seat, so we all piled in and I pulled out of the lot headed for their house, Wilma next to me and Robert next to the passenger's door. Robert had his arm over Wilma's shoulder and repeatedly pulled her close for a kiss or to nibble on her ear. That brought small giggles from Wilma each time.
In the mood he was in, Robert was talking a mile a minute and soon I found myself being asked questions about Wilma ... wasn't she a good dancer, wasn't she a pretty woman, wasn't she dressed nicely?
Wilma just kept her head down, silently and blushed as I answered in the affirmative to all Robert's questions.
It didn't take Robert but a few minutes to move his right hand to her thigh and begin teasingly bunch her skirt up while commenting on what nice legs she had.
"Behave, Robert", Wilma told him, "Larry doesn't want to see you acting this way."
"But I'll bet he'd like to see these gorgeous legs, Wilma, wouldn't you, Larry?", he responded as he persisted in gathering up her skirt in small bunches of his hand.
I was enjoying what I thought innocent fun by a tipsy, but loving husband enjoying himself. In truth, I was actually a bit complimented that he would feel safe enough to have innocent fun with his wife in front of me, obviously thinking there would be no repercussions or prices to pay.
What I didn't notice, at first, was that Wilma said nothing during most of Robert's ranting and did not stop him from inching her skirt up.
When I did finally notice, we were a well lit intersection stop light and I looked down to see Wilma's skirt halfway up her thighs.
Robert was right ... she DID have great legs.
Still ... I didn't think more of Robert's untypical behavior than a husband who was borderline drunk and having fun in a safe situation. There was no way I was going to even try to take advantage of that. That's not in me.
Arriving at their house, Wilma and I each took one of Robert's arms and made our way into the house. Robert had an arm over our shoulders and we were holding him up, more to prevent him from stumbling than falling down.
It was then I noticed that while Robert had his arm draped around Wilma's neck, his hand was firmly anchored on her breast.
He saw me looking and got a funny little smile on his face as he said, "If you think her legs are good, you should see these tits. To die for".
Wilma blushed again and I just laughed and told him that I was sure he was right, but that getting to the door was our next major hurdle.
Once inside, Robert flopped onto the couch and I sat on a love seat across from him as Wilma said that she thought that coffee was definitely in order for all of us.
I started to protest, but Robert told me to chill out and relax. A coffee would be good for everyone.
Coffee did sound really attractive at that point and I had nowhere to be other than my bed, so I sat back and relaxed while Wilma went to the kitchen. Soon I could hear the sounds of coffee making and soon thereafter smell the wonderful aroma of fresh coffee.
Robert, however, had other ideas. As soon as Wilma had left the room, he made his way to a low cabinet, opened it and took out a bottle of Scotch.
I didn't think he needed another drink, but in the safety of his own home, I also didn't think he was in any danger. It was, after all, his house and he was a big boy. I was equally sure he would pay for it tomorrow morning with a good sized head, however.
Soon, Robert and I were sipping some very good Scotch when he called to Wilma, telling her to change to something more comfortable ... maybe her little red outfit.
Questions flew through my mind. What was that all about?
Wilma didn't answer and Robert and I continued chatting while sipping our drinks until Wilma came out carrying the coffee and three cups ... in a red baby doll pajama set!!!
I almost lost it.
As she set the coffee and cups down I took note that her red bra and panties were covered by a short sheer jacket, but I could still almost see her body in enticing detail.
After pouring coffees for each of us, Wilma sat next to Robert and acted as though this was a natural and normal situation. Soon we were all chatting and talking about what a good time we had tonight when listening to an obviously very talented musician.
As we talked, Robert periodically ran his hands over Wilma's shoulders, arms and legs while talking naturally and looking directly at me.
I guess I didn't show the reaction he was looking for as at one point he stopped and asked me if I didn't like Wilma's outfit.
"It's fine, Robert", I told him, "It looks very attractive on Wilma".
"Well, you don't act as though you like it", Robert responded, Why don't you sit over here where you can see it better and show Wilma just how much you like seeing her in it?"
I liked Wilma and certainly didn't want to be part of something engineered by a drunk Robert, loving husband or not, but as I looked at Wilma in some trepidation, she scooted a few inches closer to Robert and patted the cushion next to her.
I picked up my coffee, glad to have something to do with my hands, and after walking a few feet to the couch, sat next to this vision in red.
"Now, that's better, don't you think, Honey?", Robert asked Wilma as he pulled her close for a quick kiss.
Soon we were all comfortable again in our new positions and talking away as though this was the most natural thing to do.
While talking, Robert continued petting and touching Wilma while also giving her short kisses and ear nibbles.
I was enjoying both the talk and the obviously sensual sight of this great looking woman and I could see that she was starting to respond to Robert's touches and seemingly innocent pats.
In only a matter of minutes, Robert had his hand under Wilma's top and kneading her breast while talking as though it was not happening.
After more talk and more rounds of "touchy-feely" from Robert, he suddenly pulled Wilma into a kiss and simultaneously untied the bow at her throat. Stopping the kiss, he turned to resume talking with me as he also opened her top, leaving her red bra in full view.
I was still confused, but definitely enjoying what I was being shown. Although not "busty", Wilma had a very nice set of tits that filled her bra enticingly.
Through all this, Wilma made no move to stop Robert or indicate that she was uncomfortable. Her only reaction was an occasional blush as she talked with us in a normal voice.
I could see Robert watching me as we talked and also see the tent in his trousers that told me he was enjoying this.
Again carrying on an easy conversation, Robert took Wilma's hand and placed it over his trousers. As though it was the most natural thing in the world, Wilma began softly kneading Roberts crotch while carrying her part of the conversation.
Soon, however, that too changed. Maybe due to some unspoken signal from Robert that I missed, Wilma unzipped Roberts, trousers, took out his cock and was now stroking it slowly.
Suddenly the mood changed.
"That's it, Sweetheart. Show Larry how much you like playing with my cock".
Now I was the one with a tent in my trousers. This was maybe the most sensual and erotic sight I had ever seen and it was happening two feet from me.
I couldn't help but look at Wilma's hand slowly working up and down on Robert's cock and now saw that he was openly kneading her tit with one hand and gently rubbing over her panties with the other.
"Yeah, Babe", Robert murmured, "Jack it for me. Jack my cock so Larry can see how much you like it."
The words.
I was being turned on as much by hearing Robert's words as by watching Wilma jacking his cock.
"OK, Sweety", Wilma answered, "but you'll have to carry on for a few minutes. We need a fresh pot of coffee."
Duhh!! Coffee? OK, my cup was admittedly empty, but the break in tension was huge.
"OK", Robert said as he took hold of his own cock and jacked it himself, saying, "but don't dawdle. Get back as soon as you can."
With that, Wilma picked up the pot, stood and started toward the kitchen.
"Wilma", Robert called to her.
Stopping and turning to look at him, coffee pot in hand, she asked, "Yes, Robert?"
Robert simply said, "It's time, Honey."
With a small nod, Wilma turned and continued into the kitchen.
"What a woman", Robert said while still jacking his cock. "She keeps me on a low boil all the time."
"Well, with a beautiful and obviously loving wife like that, Robert, I'm surprised it's only a low boil. I'd be boiling over all the time. We'd never get out of the house."
That caused Robert to laugh, but he responded with, "Get comfortable, Larry. Go ahead and take out your cock. I know you'd feel better and Wilma does like to look too, you know. You've been looking at us and, I think, enjoying the looking, so how about returning the favor. We'd like to see you too."
I told Robert that although his offer was tempting, I'd not be comfortable without knowing how Wilma felt about all that he said.
"Well, have it your way, Larry, but you'll see soon enough that I'm right. And it is only fair, after all."
Now I'm about as straight as they come and have never had a gay thought in my life. But maybe because Wilma had been part of the activities up until now, I admit that it was a turn on to see Robert sitting there slowly stroking his hard cock with his wife only a few steps away in the kitchen.
It seemed no time at all until Wilma came out of the kitchen with a fresh pot of coffee and my eyes nearly fell out of my head. She had taken off her bra and panties and was now just wearing the translucent cover jacket that hid very little. I could easily make out her dark rose areola and also see that her pussy was shaved clean.
"That's more like it, Honey", Robert said to her as she put down the pot and again took her seat next to Robert. "That's what we want to see, more of your gorgeous tits and pussy."
Wilma just blushed again smiled and began refilling our coffee cups.
"But you're right, Honey", Robert said, "Larry's seen your tits, but he hasn't seen your pussy yet. Open your top and stand up for us, Wilma. Let us have a good look at what a beautiful woman you are."
Without a word, Wilma stood and, arms at her side just looked at us.
"Open your top, Honey", Robert instructed her, "let us see all of you clearly."
And that's just what Wilma did. Tucking the tail of her top under her elbows she stood before us in total frontal nudity and I got my first overall look at Wilma and her gorgeous body.
Medium height and slender, her shoulder length auburn hair set a perfect contrast to her fair skin. She was all that Robert said she was, a sight to behold.
Robert continued to look at his beautiful wife while still stroking his cock, but told Wilma that I was reluctant to take mine out and jack it without her approval.
"Tell him it's OK, Wilma. Tell Larry that he should get comfortable, too, and that we'd enjoy seeing his appreciation of how good you look.
"Robert's right, Larry", Wilma told me, "Please make yourself comfortable like Robert says."
"Come on, Babe," Robert blurted, "tell him what you want, what we want and tell him so he knows for sure you mean it."
Turning back to look at me, Wilma then said, "As Robert says, Larry, you should take out your cock and jack off with us. You'll feel so much better with your cock in your hand as you look at me ... at us."
Wow!!! The words again. Just hearing this classy woman say those words put my blood pressure through the roof and my cock to a painful level of erection.
As I unzipped my trousers to comply, Robert patted the couch next to him and told Wilma to sit down and take over on his cock again.
In no time I was part of their private little erotic group, jacking my very hard cock while I watched a nude and gorgeous Wilma jack on Robert's.
"Isn't she great, Larry?", Robert asked me as he resumed kneading her tits and rubbing over her pussy.
"She certainly is, Robert", I replied, "You're a very lucky man".
"Here, Honey", Robert told Wilma, "Lean back a little so I can get at that pussy of yours better and Larry can see it."
Wilma didn't say a word, but merely turned square to the couch and leaned back against the cushions in a semi reclining position.
Maintaining his hold on her breast, Robert gently pried Wilma's legs apart and began running two fingers gently up and down her pussy lips.
All Wilma did was give out a very small moan as she continued jacking Robert's cock with one hand.
From my position next to her right leg, I could look down on a clear view of Robert's hand running over a beautiful pussy. Being shaved, I could see her generous inner lips protruding slightly and watch as they turned a slightly darker shade in response to Robert's busy hand.
"Having fun, Larry?", Robert asked. "You like watching Wilma jack my cock while she gets her pussy worked over?"
What a stupid question I thought that was ... and I told him so.
Robert just laughed at that and told me, "Well, you can play too, you know. Come on up here and show that tit next to you how much you like it. Don't worry about your cock, it'll get taken care of."
Suddenly Wilma's hand was over mine. I looked at her and she just smiled while giving me the slightest nod.
I needed no more encouragement than that and as she took over stroking my cock, I began exploring, feeling and kneading her right tit.
What an erotic sight I had before me. This gorgeous woman was jacking me and her husband while we were both exploring both her tits and her pussy.
Very soon, Robert upped the ante again by leaning down to take Wilma's left nipple in his mouth and began sucking it while still kneading and squeezing her breast.
All I had to do was look at Wilma's face and I was down sucking on her right tit as well.
This was far more than I ever imagined with these two and I was enjoying all this immensely.
Wilma was jacking both of us and her husband was now running two fingers in and out of her pussy. The sight alone was about to make me cum.
Wilma then stopped jacking Robert and ran her fingers over the head of his cock, which was shiny with a good amount of his pre cum lube. Then, while looking at first Robert and then me, she raised those wet fingers and licked Robert's precum fluid from her fingers.
"Yeah, Honey, suck my cock juice", Robert told Wilma, "and tell Larry how much you like it."
"I do like it, Larry", Wilma said with her fingers still running over Robert's cock head and then into her mouth. "It's warm and so sweet. It tastes wonderful."
"Wonder what Larry tastes like, Honey? Think his is as sweet as mine", Robert asked her.
Wilma didn't reply, but only looked at each of us in turn.
"Go ahead, Honey, try it and tell me what you think."
In no time, Wilma was running her fingers over my cock, gathering my precum fluid and licking it from her fingers.
"Well?", Robert asked her, "What do you think?"
"It's very good, Robert", she said to Robert, not quite as sweet as yours and a bit different taste, but just as good in a different way."
"You like it, though?", Robert asked.
"Oh, yes", Wilma replied, "very much"
"Well, then get me some", Robert told her, "If it's that good, I want to see for myself."
Now, rather than lick my precum from her own fingers, she extended her wet hand to Robert's face and I watched as he licked her fingers clean of all my precum.
"You're right, Honey", Robert admitted, "Larry does taste good."
As I said, I'm a super straight and always have been, but the sight of Robert licking ... no ... sharing my precum with his wife was a huge turn on.
Suddenly Robert stood and as he began removing his clothes, said, "I don't know about you two, but I'm ready for a snack."
Once nude, Robert knelt between Wilma's legs, pulled them wide open and began licking up, down and around her pussy. She was obviously enjoying his attention because she scooted a few inches closer to the seat edge and raised her hips to meet his mouth.
Now I could see that Robert had his mouth over her whole pussy and was licking it full length as far inside as he could. Periodically, he would suck her protruding inner lips into his mouth and lean back as he gently stretched them away from her body.
With his fingers working into her pussy, Robert leaned back, looked at me and said, "Wait a few minutes, Larry. A bit more on her lips and they'll hang out over an inch and you'll see a beautiful sight."
With that he lowered his head back into her and resumed licking and sucking all over her pussy, but paying good attention to both her inner lips and an occasional kiss on her clit.
Soon, I could see her growing response and within a matter of minutes I witnessed another beautiful sight ... Wilma in the throes of a big orgasm.
Then, with Wilma panting slightly, a bit of sheen from perspiring and pussy open and red as she remained laid back before us, Robert got onto his knees on the couch beside her and offered his cock to Wilma's face.
Without hesitation, Wilma opened her mouth and began sucking the head of Robert's cock while jacking the shaft with her hand.
"Don't let all that go to waste, Larry", Robert told me, "That's some of the best pussy you'll ever eat, I can guarantee you that. Get in there and keep her happy while she sucks me off."
I was so turned on that I couldn't see straight, but was obviously too slow in reacting for Robert.
"Come on, Wilma", "tell Larry he can eat your pussy ... that you'd like him to."
"Yes, Larry", Wilma said as she stopped sucking on Robert, but continued jacking him as she turned to me, "You can lick me there if you want."
"Jesus, Babe!!!", Robert exclaimed, "Tell him. Tell him so that he knows it and use words that he'll understand."
Still jacking Robert's cock and looking into my eyes, Wilma now said, "Yes, Larry, come eat my cunt. I want you to lick and suck my pussy. Put your tongue into my wet cunt and make me cum. I want you to."
Needless to say, those words put me into action and I immediately had my face buried between her legs as I licked her cunt and sucked on those long, soft lips. She tasted wonderful and her pussy leaked so much of her juices that it ran down my chin. Soon my entire face was coated with her ... with Wilma.
It didn't take Robert long before I heard him grunt and looked over Wilma's pussy mound to see him stiffen as he came in Wilma's mouth. Within seconds, Wilma froze and came too with little shudders to her whole body.
After we had all come down and were again breathing normally, we sat as old friends would, still nude, drinking now warmed over coffee and talking.
"How did you like that, Larry?", Robert asked. "You ever taste such a sweet pussy in your life?"
"No, Robert", I replied, "I must admit that it was a once in a lifetime treat and I'll always remember and appreciate the gift you two have given me."
I could tell that my words had pleased Wilma from the slight smile and tiny flush I saw on her face and breasts.
Robert noted it too. Within minutes, he was hard and back to licking her pussy.
"Want to get her ready, Larry?", he said between lick strokes. "I'm about ready for round two."
At Wilma's invite, I moved to sit next to her and began playing with her tits as I heard and saw Robert really getting into Wilma's pussy.
Soon, she was moaning into his face and also began stroking my cock to another huge hard on.
Before I knew it, she was pulling me up onto my knees beside her and had my cock at her face. Now, with Robert eating her pussy, she began sucking my cock while jacking on the shaft. This woman wanted me to cum, there was no doubt about that and I wasn't about to disappoint her.
My head rolled back and my eyes closed as I enjoyed the utterly wonderful and erotic feeling of this beautiful, sensitive woman sucking perfectly on my cock. As my feelings built toward a hard orgasm, she momentarily stopped and then began again ... only it felt different.
I looked down to see Robert laying on Wilma, his face next to hers and with the head of my cock in his mouth. She was still jacking the shaft and looking up at me with the softest eyes, I have ever seen.
He likes this", she said, "I like this. We like this. Are you alright? Is this OK with you?"
While I was in blowjob heaven, Robert had moved up from eating Wilma's pussy to fucking her. I was so gone into what she was doing to me that I hadn't noticed. This put his face right next to Wilma's as she sucked me beautifully. It was no extra effort for her to point my cock at Robert's mouth and for him to take me in and begin sucking.
I had to admit that, although different, it still felt really good.
All the while, Wilma was jacking my cock as Robert sucked it and rocked his own cock in and out of her pussy.
"I had no idea.", I told Wilma. I wouldn't have guessed it in a million years, but it does feel good and my overall erotic feelings are running high", I continued with a smile at her lovely face.
Looking relieved, Wilma began trading my cock back and forth with Robert. She'd suck on it for a minute and then point it at Robert so he could also suck on me.
"Do YOU like this, too?, I asked Wilma. "Does it turn you on to watch Robert sucking my cock?"
"Oh, yes", she replied while still jacking my shaft. "Robert is fucking my pussy and this always gets him really hard. I can feel his entire body against me, his chest on my tits and we get to share sucking you off. Plus", she continued, "I do like to see men sucking each other off. I get wet just thinking about it."
Now this evening had been filled with a whole new set of experiences for me and this was the newest of all. And the strangest, but what I found even more strange was my reaction. I was still hard, still getting close to cumming, felt like I was with two real friends and ... wanted this woman to be happy and I told her so.
"So long as you are happy, Wilma, I'm happy too. If this pleases you and turns you on then I'm more than OK with it". There I had to laugh.
She looked up at me trying to see why, so I told her, "You two have given me a tremendous amount of pleasure this evening and, though it's all very new to me, it feels really good. I guess it's true that a mouth is a mouth and I also like seeing you watch and seeing your pleasure, so, all in all, I'd say it was a win win all around."
I knew Robert had been listening to me and he picked up his pace on both his wife and my cock. It didn't take long for all of us to reach the point of no return and we all had a great orgasm together.
Robert pumped all his cum into Wilma's sweet pussy while I gushed cum like never before into first Wilma's and then Robert's mouth. As we started to relax, they stayed joined at Wilma's pussy while Robert allowed my cock to soften in his mouth.
When I was totally deflated, he relinquished his oral hold on me and kissed Wilma passionately. Then he lowered his head to her chest and we all just lay there in the afterglow.
As we disentangled, Wilma went to the kitchen, for cold drinks this time, while Robert and I just laid back on the couch with one foot on the floor, one drawn up and facing each other.
Gert
- 12.12.2022
- 19
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