This story is a work of fiction and contains descriptions of explicit sexual acts between a mother, son, a transgendered female and lesbian adults. All characters are Forty (40) years of age, no matter what they tell you. If this type of content offends you or you are under the age of 18 do not read it.
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Copyright 2023, Rikki all rights reserved
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At an early age mom and I were living in an apartment on the fifth floor of an old warehouse. We could walk out onto the roof of the fourth floor below us and had what was essentially, a deck, a quiet, private deck. We practically lived there in the spring and summer. We grilled, ate meals, did home work and entertained out there. Wanda, mom's best friend was our most frequent guest. She actually had an apartment in the same building but it was like she lived with us most of the time. She and mom laid out in the sun on the roof and drank appletinis sometimes, listening to jazz and occasionally getting a little bombed. One day It hit me that when they were both out there, they were making out and petting. I stood in the doorway watching for a few moments before I realized that I should give them some privacy. You may ask about how much privacy is on a roof top of an apartment building. However the answer in this case is - quite a bit. There were no there buildings around us that were that tall. And besides that there was a half wall all around the roof for safety but provided privacy also for those who maybe laying on blankets on the light gray roof.
A moment after closing the door they came in. They were affectionate in each other's arms and nuzzling the other's face.
"Look at that handsome young man over there, Willa." Wanda said to Mama. " I wish I had a handsome man like that to kiss me and dance with me..." She mumbled more but I couldn't hear it.
"Ricki, "Come over here, honey." I did as she asked. I was of an age when the attentions and affections of women and girls were becoming pleasing to me. The next thing I knew mom was kissing me on the face and her body was pressed against mine. Then another surprise happened and I felt Wanda's chubby, curvy figure press in from behind.
"Ricki today is Wanda's birthday, why don't you kiss our birthday guest?" I was somewhat in shock but not immobilized. I turned toward her and saw her wide moist mouth come down on mine. It was a two second education on what's so great about kissing. I was hooked. The soft encounter was sooo pleasing. The gentle scent of the appletinis they'd been drinking added to my pleasure. And then... her prehensile tongue split my lips asunder. WOW! It snaked into my mouth and made me think of what it maybe like to suck on her nipples. I became aware that both of these beautiful women's bodies were pressing in on me in a way I'd never considered previously. Well maybe not, Its hard to know what I knew and when during my sexual developement.
"Ricki, I think Wanda wants you to massage her nipples too." Mom chimed in. I realized what a strange circumstance I found my self in. My mom asking me to French kiss her friend. Never the less, my hands found Wanda's nipples (as well as the rest of her bosom) and her soft plumpness beguiled me and I nuzzled into her personal space.
I worried for a moment when I noticed that I was getting an erection and It was pressed against Wanda's thigh. Sweat shorts did little to hide the fact.
"Willa, I think your little man is a bigger man than we thought." Her leg moved over and around my hard penis and she planted a wet kiss on me again.
Wanda's nipples were erect and she responded with moans and writhing. My excitement was mounting and I was pondering the next step. Then I heard Mom.
"Here Ricki. You must be thirsty."
"What is it, Mom?" I knew what it was. It was an appletini. I'd mixed enough of them myself to serve Wanda and Mom. I just didn't know how to transition from serious making out to logical conversation.
"Drink it slowly, honey. Wanda and Mamma will give you something to watch while you sip your drink and then we have a little surprise for you." She watched me take a sip. I made a face. It was strong and sweet and reminded me of really sweet apple juice. In a few moments I knew I was going to like appletinis. Mom and Wanda watched me and Wanda gave me some advice.
"Just sip it Ricki. I know it tastes good but if you drink it too fast it'll make you really sick. Now I know you liked kissing me and playing with my breasts, didn't you?" I nodded, my attention returned to the pleasure we were having. "Well Ricki why don't you just sit there and watch us. I know you'll like what you'll see."
And I did enjoy it. Mamma licked Wanda's face and then kissed her with Mamma's own tongue going into Wanda's face. Their excitement mounted quickly they started pulling off each others swimsuits and reaching for each other's bodies, hands touching tushes and reaching between thighs. Soon the suits were gone. And they were in Mom's bed. I too, took off my shorts and tee shirt and even my underwear then.I was so shocked that I thought to get up, but the moment I began to move, I swayed and felt a little dizzy. So I stayed put and a smile crossed my face as I saw two beautiful lovers cavorting in front of me, naked. Looking back its hard to tell what I knew about sexuality and what my feelings were at that exact time. But Mom and Wanda seemed so natural and loving and friendly. The one thing I did know was that I was aroused. I never had imagined seeing one woman's breast pushed up against her partner's, or a hand slipping between the other's thighs and the vocalizations and moans, or the effect of the whole on my little wee wee still erect from live contact with Wanda and now throbbing with a life of its own. Of course I held the wiggling thing to caress it and discovered that I could give myself pleasure. Recalling that time, I was close to cumming right then but instinctively backed off to prolong this adventure. Instead I caressed myself mimicking what the adults were doing and almost going into a trance.
They were moving a bit less but more intensely. I think Moma's hand was completely inside of Wanda's vagina and Wanda was shuddering with pleasure. They were laying juxtaposed with each one's head at about the groin of the other. Wanda massaged Mom's breasts, pulling and twisting and pressing, oh my.
"Ricki," mom called out excitedly. "Come over and lay next to Wanda. Put you arm around her and kiss her." My right arm went round her neck and my left caressed her abundant tummy as my mouth sought out her's. Suddenly Wanda's back arched. Then she cried out, "OOOh Willa, a huh, huh, Ooooh, OH, Oh, Ricki I'm cumming! Ohh god! oh baby.
I am better equipped in vocabulary to describe those events today than I was back then. Wanda had grabbed on to me and held me with superhuman strength, it seemed. Her body shuddered in rising and falling waves of rapture. We laid like that for a long time. When ever I moved she held me tight, and at the same time my naked cock moved along her thigh and was rewarded with throbs of pleasure. Then after a while it seemed like she was asleep. I surreptitiously, I thought, rubbed my erection against her thigh some more. I even started a slow rhythm and was content to stay that way. But then...
"Willa, Ricki wants to fuck someone. What do you think we should do about that?"
"I want to make love to my little man and I want you to play with us too." They started to untangle themselves from each other and from me."
"That was one of the best orgasms I ever had Willa." Wanda exclaimed and pecked Mom and then she kissed me also. I had finished my appletini after getting up.
"I like how this tastes when we kiss." I observed.
Mom the declared, "Well honey, we'll have to kiss some more then." Her mouth locked on to mine as Wanda's had earlier. Mom's was different though. Wanda had been more aggressive and horny, Mom was gentler and more given to being pleasurable. Mom was slimmer than Wanda but when her naked skin made contact with mine it was a tactile celebration. She pulled me down on her body as she rolled over in the bed. "Ricki, do you want to put your wee wee into mine?" Her smile was beatific. As I arched over her body she held my penis gently, rubbing it in the wetness that adorned her body from her carnal knowledge of Wanda. Instinctively I lowered myself as she guided me into her.
"Oh god, mommy!" I wanted to tell her how wonderful she was making me feel. But I was over whelmed by the sensations of her horizontal dance with me. She possesses the ability to clamp her vaginal muscles around my wee wee and milk it. She pushed her nipples into my mouth which was pure joy. But it also allowed me, or her or both of us to settle into a rhythm, a delirious rocking and plunging, naked on naked wrestling encounter. "Oh god, mommy, you're so beautiful, I love you. I love making love with you." She smiled and kissed me.
"There-there you are my sexy man. You're going to have to take care of Wanda and mommy in bed. Do you think you can do that?"
A shudder ran through me with the delight of knowing that there will be more of this lovemaking in the future. And as much as I loved mom, I also loved Wanda. I looked around to tell her so, but didn't see her right then. Mom's and my sweat was making our bodies slick and sensual and I got lost in a few moments of heightened action, thrusting and feeling her meet my thrusts and the hunger and longing in each of those thrusts.
That sneaky Wanda! Out of the clear blue (I heard it before I felt it) she swatted my bottom with a distinct 'crack'. Oh but god, did it turn me on. Well one good surprise deserves another. I then felt both of her hands on each of the globes of my bottom, playing with them. She massaged them, rubbed them in opposite directions, spit in between them and spanked me, harder than before but still playfully.
Oh my, what happened next I'll remember even if I get Alzheimer's. Her blessed tongue came rippling through the valley, played over my anal opening and then plunged into me, vigorously shoving her way through and causing me to fuck poor Mamma so hard and passionately.
"Mamma, mamma, Wanda's tongue its,.. its inside my bottom! Oh Mamma. Then just as suddenly it was out. She kissed both cheeks on the way out. Mamma was gently pulling her nails down my back. I was kissing her continuously, tasting her tongue and the faint essence of appletinis.
Then a wet sensation flowed between my buns. It was oily. It was followed by Wanda's finger which went straight in to my anal sphincter. She timed it so that I would thrust deeply into Mommy. It worked. Then she twisted and twirled her finger around and around until she found my prostate. It electrified me.
"Mamma, something is happening to me! Oh Mamma!" I was shrieking. I came in waves and shudders and waves of shudders. The indescribably delicious feeling of spermatozoa coursing through my penis and the loving, tender contact, the skin to skin sensations with Wanda, Mommy will be with me forever.
I'm not sure but I think I fell asleep then, naked and inside Mommy.
Of course living a fantasy like this is all well and good. Actually its even better than that, but you know what I mean. Real life rears its head and seeks to interfere. It was decided that I would be home schooled. That relieved me from enduring a whole bunch of social pressures many that I had no clue about.
Mom and Wanda had formed a business partnership in which they designed lingerie. From time to time they had to go uptown, downtown or out of town for business meetings and occasionally they brought someone home. And sometimes when we had a guest the three of them would be trying on lingerie and having a few drinks. And sometimes when the lingerie went on there was an even bigger production about taking it off.
"Oh was that Champagne I spilled down your front? Tee, he, he?" one customer who didn't know her sheets from the wind breathlessly mused. She leaned down and licked Wanda breasts and kissed her skin while she removed her bra and began to kiss in earnest. I watched a few of these encounters discretely as I was not allowed to join in, unless in time Mom and Wanda agreed that one or another guest was trustworthy.
We did continue to make love with each other. And occasionally they would bring around a friend who they'd known for a longtime and had been a sexual partner with either or both of them. All of these guests were women. In rare occasions I was invited also.
Then there was one time.
Wanda had been out of town but was due back and Mom wanted to do something nice for her. "Ricki, honey will you help me do something nice that will be a nice surprise for her?"
"Sure Mom." I had learned quickly that if I was a happy and enthusiastic member of the household we would have wonderfully fun adventures in the bed room.
"I want to arrange the hors d'oeuvres on your naked body for the party. "I must have gasped, because Mom thought I was shooting down the idea. But I corrected that quickly. I loved the idea of laying on the table, naked, with little snacks arranged all pretty on me. I hope that the partyers will linger and play while they nibble. "Oh that's a relief, Ricki. I thought you'd like that. Now I have to check on the masseuse."
"What's a masseuse?" It was a funny sounding word. "She's someone who rubs your muscles and makes your body relax." Just then the caterer arrived and it was Janelle, a friend of ours. She had the table set for six in a few moments and had wonderful smells drifting from the kitchen. The kitchen was then off limits to everyone else. But I know Mom snuck in there when I heard Janelle yip when Mom pinched her bottom. Then in a little while our friend Waverly arrived with the masseuse. She was a rather tall woman, shoulder length black hair. She wore a lot of makeup but it was pretty. She brought a massage table with her. It was all folded up and had little wheels. "Everybody, this is Shelly, masseuse-mas-fina. There's a name they call her customers. "Lucky." Mom exclaimed. "She's also wearing one of Wanda's designs. So get a good look at it while you can." It was a sheer yellow top that had printed grass, still sheer, from her breasts to her hips with faded flower pedals in the breast area and two bright red flower centers on her nipples, which were erect. She didn't appear to be wearing panties but she did have an alluring sashay in her walk.
I was escorted to the kitchen where I laid on a serving cart. Janelle came pirouetting over.
"There's one thing we really want to display on this appetizer assortment. I want to see this wee wee standing up and waving the flag. Okay Ricki?" She didn't wait for my answer, she just bent down and suckled my penis into her mouth until I was erect and excited enough to stand on my own, as it were. She laid a circular dish with a hole in the middle, through which my now throbbing tenderloin protruded. Then she spooned in a warm artichoke dip. The warmth helped my erection stay up. Sliced fruit and crudites adorned my thighs and savory charcuterie was on my arms. Janelle came by and played with my cock and kissed me from time to time. Soon someone called out "She's here!" and Janelle wheeled me out to the dining room. Mom winked at me and licked her lips.
The door opened and there stood Wanda. Everyone yelled, "Surprise!" and she broke out in a gorgeous smile. She hugged Mom and everyone else and then her eyes landed on me. "Oh, my god Ricki! You look good enough to eat. She dropped all of her stuff right on the floor and bent down and sucked my trouser trout into her mouth just like Janelle had done a few minutes ago. Her tongue swirled around me and then under the tip. She removed the dip dish let me fall out and then she sucked my testes and I was so turned on that I had to be restrained by Mom and Janelle from knocking food on the floor. Wanda then had me back in her mouth going up and down and up and down. In the periphery I saw everyone taking their clothes off and a few entrancing, hot caresses (Oh gawd). My body went rigid and I looked at Wanda and she smiled.
"Cum for me now Ricki." I did and a little landed on her lips but she swooped down and sucked it in and swallowed the rest. She continued to tongue massage me for several minutes and I nearly cried, I was so happy.
"The others gathered here were watching Wanda's wanton actions or beginning some of their own. Waverly and Shelly closed in on Wanda and started removing her clothing.
"What's up, my pretties?" Wanda asked.
"This is your company bonus surprise." Mom cooed.
"Oh. You mean ravaging your tasty son wasn't a surprise? I'm ready to kidnap him and keep in my hidden lair in the woods." She turned to me and added, "It has all of the comforts, my lair has." Then she winked. Shelly had pulled off Wanda's skirt and was pressing her slim body against the fulsome curves of Wanda. Shelly maneuvered Wanda to the massage table and coaxed her to lay on her tummy.
Mean while Mom had removed the appetizers from my arms and legs and tummy. Thinking about what I'd just heard I asked Mommy, "Does Wanda really want to kidnap me?"
"If she does, you could spank her naked bottom." I think Mom was well on the way to being lit and thinking of what she wanted to do.
"Now this should be interesting, Ricki. Shelly is going to give Wanda a nuru massage." Mom turned me back toward the show, wrapped her arms around me and I felt the curves of her body imprinting on me. Shelly had only been wearing panties at that point, which now went flying. Shelly poured massage oil all over her own body and made quite a display of distributing it everywhere. She was shining and dripping as she climbed onto the massage table with Wanda.
It was then I think that I saw that Shelly had a penis. 'How odd' I thought, 'That this beautiful woman was born with a penis.' Shelly's oiled butt slid along Wanda's back, eliciting "Oh my god"s and "More, more, more" as The slick, naked beauty massaged with every part of her body. Wanda was pretty slippery looking and had a naughty twinkle in her eye.
"My god, how can anything feel this good?" Wanda exalted.
Momma had been wearing a sari and a bikini top but as she held me close I felt the sari fall to the floor and then the wetness of massage oil dripped and trickled down my back. Soon our bodies were sliding against each other. I could feel Momma's breast splayed out toward my arms spreading more oil and telegraphing her excitement. She even massaged my nipples. I noticed the thickening sensation in my organ.
My eyes caught Waverly on her knees in front of Janelle. I suspected so much but didn't have the knowledge or experience to know what was happening exactly.
Wanda had not moved much, so far, but Shelly was now hovering above her almost horizontally and face down. Shelly lowered her chest onto Wanda's back and slid down her back, now down to Wanda's bottom, and now down to Wanda's thighs. But Shelly's face was between those bountiful buns and when Wanda squealed I knew something had happened. Then Shelley was back up, chest to back with Wanda and her hips were twisting above those tempting buns. Then she lowered her hips and began moving parallel to Wanda's body.
Suddenly Wanda shrieked and began laughing, "You impish, naughty, sissy. Now reach around and grab my boobs and fuck me good. I knew Shelly was thrusting purposefully and was quite excited when she swatted Wanda's buns and declared, "I wanted to find a nice plump one like you today, you wicked, wicked Wanda. Milk my sissy cock deep inside of you. Momma was moving us away and soon we were kissing and caressing and my erection was returning. At some point Wanda came and things were quiet for a few minutes.
Mom broke the silence then, "Ricki what kind of lingerie would look good on Shelly, do you think?"
"Oh, let me think." I gave it serious consideration and then answered, "The asymmetric bikini ensemble." This combo had a black and white checkerboard bra cup on the left. On the right were shingled layers of lace alternating in black and white. The bottoms were similar but a lace belt went all the way around. It was part of the 'Let's Play Nakies' collection, for the coming Spring.
"Oh, that's so clever Ricki. We'll have to have her try it on later. Do you think she's pretty?"
I responded by nodding enthusiastically, which surprised me. I hadn't realized that I had an opinion on the subject. But when I looked at her again and noticed her lithe dancer build and her easy smile and sexy carriage I knew that I would love to fuck her myself. I was confused though. I would have wanted to fuck Shelly, but was mommy asking if I wanted her to fuck me? I never considered the possibility before and it didn't really appeal to me.
"Do you think you want to put your wee wee in her like she was doing to Wanda." My excited smile was answer enough for her which was good because I think I would have been too tongue tied to give a coherent answer. Mom waved Shelly over. She sashayed in cat like movements and bowed her head to Mom and only raised her eyes when Mom lifted her chin. "Lie down on your table Shelly. Ricki here, is going to tell you a secret, but he needs to no what it means first." It was the most erotic sensation just watching her manipulate her body onto the massage table and into the prone position and purr like a cougar.
Momma dipped her hand into the bowl of warm massage oil and poured the wonderful stuff on my chest and spread it all around my chest and arms. She was so close that her erect nipples were touching me and I nearly melted. She continued on down and spread more on my thighs and legs, between my buns. She groped my testicles and her mouth suckled my now turgid lance of love. Her tongue swirled and swished and in a couple of seconds she pulled away.
I was suddenly disappointed, wanting more of that. Then Mom called out to the other three women. "I've got one leg."
Wanda Called out for the second, Janelle took my arm and had my hand between her thighs and was riding my hand. Waverly who was caressing Shelly's bottom with oil at the moment, gave her an audible swat on her tush and said, "I always get so jealous of you when we go out." She broke out laughing and took my hand. Some one counted to three and they all lifted me up and moved me over Shelly's fascinating form. For a second I had doubts whip through my consciousness, but I saw her buns writhe against each other and all doubts fled.
It was like I lost consciousness and I woke up with my prong on Shelly's tender tushy. The women kept hold of me and moved me back and forth and someone with a free hand kept guiding my wiggly wee wee into Shelly who was arching her bottom up to me. Then they lowered me down on her completely. That's when I became aware of the constriction, the tightness, the pressure,...OOOHHHhhh god! I involuntarily began thrusting and the exquisite pleasure increased for every muscle twinge and every thought of movement. My hands encircled Shelly and found her breasts and nipples. My face and nose nuzzled her hair. I wanted to tell her how sweet she was and how intimate I felt. I opened my mouth and surprised myself.
"I love you, Shelly. You're so beautiful and you make me feel so wonderful."
"I love you too, sweetie. And I love you deep in my ass." She replied quietly. Then I noticed that she was making her buns swish and enclose more tightly, my penal probe. I could only respond with more thrusts. I found that the tip of my presence in her was encountering some resistance to me backing out.
"Oh, oh I like that."
"You like when I do that to your weapon Ricki?"
"I love it, Shelly."
"I'm glad you like it. Whenever you want me to do it just spank me."
I giggled, "Spank you?"
"Sure, baby I enjoy that and I know how to reward you too. Go ahead try it."
"Okay." I said with a little trepidation. I swatted and it was more of a playful pat, so I did it again harder. I felt her grasp of my cock's mushroom head almost like she had a tongue down there milking me. I was so happy to be riding her that having to slap her butt seemed like a distraction. So I concentrated on deeper and harder thrusts. The sensation of our bodies slipping against each others naked skin was wonderful, too. But I had to hook her shoulders with my hands to keep from sliding off. My pace was increasing quickly. Our bodies, lubed with oil now had the additional sensations of sweat which heightened the sensations even more. I was thinking that I would probably cum soon. But in a day for surprises, one more just arrived.
Momma inserted a well oiled finger in my bottom. She rotated it back and forth and touched something that pushed me over the threshold. I felt liquid squirting out of me. I felt Shelly squeasing me and I felt Momma gently massaging me there, inside. I was crying with happiness and joy. My body convulsed and throbbed, while Shelly's every move seemed to compliment what I was experiencing.
"After a moment I just collapsed and laid on her back in our sweat and oil and heat. If I even gave a notion of a thought about it, my penis throbbed. I did not want to move but thought that I may feel heavy on Shelly's back. As I started to shift my weight to alight from the table Momma gently restrained me. At the same time Shelly's magical inner muscles grasped my cock again. Thoughts flooded my mind about making love again even though I was exhausted.
"Hey sweetie," Shelly cooed, "You don't have to go anywhere."
"Learn to experience the sweetness of the aftermath." Mom whispered. I processed that idea for a moment.
"You can even go to sleep if you want to." Shelly murmured. I felt a sheet being pulled over me. It was my last conscious thought with my tenderloin still inside of her.