It has been over six years since my last journal entries. So much has taken place during the years and then COVID hit - putting a damper on most things.
I stopped writing about my taboo relationship with Maria and Carl, but it's truly worth revisiting again. Reading my past stories, you would be aware of how my relationship with two teens developed into one of the most fascinating chapters of my adult life. In fact, for over a year, we enjoyed each other's lust and enjoyment in the privacy of our home. Sex was often spontaneous and in every space in our home - bedrooms, kitchen counters, bathtub, patio, and basement.
Maria, an attractive girl in her late teens, took us both deep in her cunt for hours at a time. During that time, she also enjoyed watching Carl and me enjoying the taste of each other's cock and cum. In time she opened her ass to us for further delight and our double penetration soon became the norm.
Like all good things, it all started to end when Carl went off to an out-of-state college. Maria and I kept up the sexual escapades up to the point that she started sleeping with me every night. I would have been the envy of most guys if they knew what happened at my home. A middle-aged guy and a voluptuous teen with a kick-ass body sleeping together. But again, Maria moved on as we decided she needed to be with someone in her own age group. Besides, no one in a thousand years would have condoned a relationship between a fifty-something-year-old guy and his teen stepdaughter. Within two years she met a nice guy and they married. Sometime after, she gave birth to a son and moved out of state.
Between late 2018 and 2019, things became normalized for me again. I started dating a nice divorcee, who loved sex, but not the degree of kink I enjoyed. By 2020, COVID was beginning to raise its ugly head, so things went into low gear. For the first time in years, my sexual escapades came to a grinding halt. I longed for the past and masturbation took over my senses. Luckily, one night my cell phone rang and I noticed the long-lost number of our TS friend Tatiana.
In a slight Russian accent, she asked, "Hello it's good to talk to you again. Do you have Carl or Maria's telephone numbers? My phone was hacked so I needed to update my new phone."
I provided her with their numbers. We made some small talk and I asked, "Are you still living at home?"
"Yes," she whispered.
My mind quickly went back the years and thoughts of the many encounters reappeared in my mind. Tatiana was the first transexual I ever encountered and a good friend of Carl and Maria's. Tatiana was attractive and a passable trans girl.
I'll never forget the first time I reached into her pants to find an engorged clitty in my hand.
"Do you think you can come over?"
"Yes!"
We hung up and I started tidying up the place. I hadn't seen her for two years, but the four of us played numerous times in the past. I wondered how she looked. An hour later she stood at my front door.
"Hello," she said with a deep smile.
"Hello, please come in," I offered.
She removed her coat revealing a black low-cut dress. Her tits were pushed together in a tight cleavage. Sheer stockings outlined her shapely legs. Black heels with two-inch spikes elevated her to my height. She reached in and hugged me followed by a deep, wet kiss. My hard erection brushed against hers. Within minutes we were back into the bed we had all made love in years earlier. An hour went by, then two. We both came numerous times and our sticky jizz covered each other's bodies.
As we lay exhausted, I had time to admire her physical beauty. She hadn't changed. She sported a very trim frame and tight ass and body. Her boobs were meticulously formed and accented with dark wide areolas. The nipples were eraser-sized and firm. Her "clitty" was well-formed but with a thin shaft. Its ability to shoot cum remained unchallenged.
"You have a great body," I whispered.
She gave me a deep kiss and thanked me.
I recalled the many stories she told us of her transition period - Breast augmentation and hormones. She stopped short of pelvic surgery, but she was extremely feminine anyway. I also recalled how his transformation started and how motivated he became before becoming a "her".
She closed her eyes and said, "It was a very sexy time for me. I had very close physical features to a woman - a small frame, thinner legs, and light hair. It was an incredible time preparing to dress. I became horny beyond belief."
I nodded and smiled.
She and I continued to date until the COVID lockdowns. At that time nobody was dating, much less fucking. Every so often, however, Tatiana would text me and we would mask up for a short session and exchange blow jobs. Our sexual escapades continued for a couple years-luckily for me since I was dating no one else.
All was well. By the time, COVID winded down, I made the conscious decision to sell the home I lived in for decades. It was just too big for one person and the maintenance and upkeep tired me. I reached out to the two kids and asked them to let me know what stuff they wanted to keep. Although they lived a great distance away, they never relocated all their things. In several weeks, I had a good idea of what they would keep and what I would donate or throw away.
Maria, the more sentimental child, wanted to sort out some of the things personally, so several weeks later, she planned a trip home. It was my assumption that her husband and child would accompany her, but two days prior to her arrival, she indicated that she would come alone. It was just too far for all of them to make the trip. Sad that I wouldn’t see her husband and baby, I still welcomed her arrival.
I saw her rental car pull into my driveway and she stepped out as I opened the front door. A warm smile lit up her face as she walked up to the door. We embraced and I kissed her on the cheek as she squeezed me.
“Oh my God, how are you?” she asked.
“I am great. You look wonderful. It’s amazing how much you matured in the last couple years.”
Maria was no longer the teen I had known so well. She was twenty-four years old, and a mother now. Her face was tanned and her stunning figure hadn’t been affected by childbirth.
I grabbed her bags and we went inside. She made coffee just like she did when she was living at home. We sat for an hour and talked about family, events, and her new life.
“I love being married to Paul,” she said. “And the baby sleeps most of the night, so I am finally getting my sleep again.”
I had only seen the baby twice since he was born during the peak of the COVID outbreak, so she showed me hundreds of pictures. It was good to see Maria again and she brought life back into the boring house.
“And, I wanted to tell you something. I’m pregnant again. It’s only six weeks, but it was confirmed last week.”
“Oh my God,” I cried out. “That’s wonderful. Congratulations. I’m so happy for you.”
I hug her, and she filled me in with all the details. She would stay with me over the entire weekend, so it would be a good time to catch up. We had a number of things to sort through at the house and several buyers were already interested in the property. Within two hours, she shuffled through her things in her old bedroom.
Maria was sorting through some old photos she stored underneath her bed. She sat on the floor as she went picture-by-picture. I noticed her facial impressions as she went through some of the older photographs of her actual family from Mexico. Her teen figure changed a little over the past six years. In her mid-twenties, she still had a kick-ass shape. The khaki shorts she wore were shaped perfectly around her body and her long tanned legs extended down to her perfectly manicured feet and toes. White summer sandals contrasted her tanned feet perfectly.
My God, I saw her naked hundreds of times and she still turns me on. Oh well, things change and I’m very happy that she has a new life and family.
I refocused on helping her clean out her stuff, but I couldn’t help but think of the past. After a day of work, she asked if we could order take-out from her favorite restaurant. I placed the order and poured myself a glass of wine. I knew she wouldn’t drink due to her pregnancy. We sat and relaxed on the patio while we waited for the food delivery. Our conversations varied from the things we all talked about many years earlier. Maria was a mature woman now and her life experiences changed.
“So what about you?” she asked. “Why aren’t you seeing anyone? Carl and I were hoping you would have continued dating Ellen.”
“She was really nice, but it didn’t have the spark I was hoping for,” I answered.
Ellen was a nice lady but lacked the sexual prowess I hungered for.
“Well, I’m sure you will find another lady friend. You are handsome and a great lover, so I am confident that the right one will come along.”
Wow, I’m honored. Maybe the wine is affecting me, but that was one hell of a compliment. Especially the "great lover" part.
When dinner was delivered, we both ate and decided to take a dip in the pool. This would likely be one of the last times we would enjoy the water. I was on my third glass of wine, so was already light-headed. I'm not used to drinking anymore. No one to drink with!
Since Maria, didn't think to pack swimwear, she put on a pair of denim shorts and a tee shirt. We both jumped in and enjoyed the water that fine summer night. After a few minutes in the pool, we dried off and sat on the patio. The Tiki torches lit the patio area with a warm glow. The night air turned cooler and Maria wrapped a towel around herself. We talked about her family, being a mother, and her life growing up at home.
"So how is Paul treating you? Is he spoiling you like I did?" I asked while laughing.
"He is great. He is also a good dad. We are both looking forward to our next child," she replied. What we lack is the spark that Carl and I shared. Actually, the spark you provided too. You developed us sexually."
She got up to pour me some more wine. As she dropped the towel, her soaked Tee-shirt revealed two perfectly shaped tits. Her large nipples, erect from the cool air stood out proudly. Her arm brushed mine as she poured the wine. I don't know what I was thinking, but I needed to admit something to her.
"Maria," I stuttered. "Maria, those times with you and Carl were some of the most exciting times in my life. It probably was inappropriate, but it was erotic."
As she sat on my deck chair, her long black hair shined from the glow of the flaming lights. She touched my hand and rubbed my arm.
"To answer your earlier question in more detail... Paul is great, but I missed the fucking I experienced when I lived here. Paul and I have sex, but not to the degree we shared here at home."
Without saying a word, Maria lifted her T-shirt up revealing her breasts. They were as magnificent as I remembered, but fuller due to childbirth. There was some noticeable sag, obviously due to nursing the baby. Her nipples and areolas were dark and sculptured.
"I'm still lactating," she said. " I have been breastfeeding him since birth."
She squeezed her tit between her thumb and index finger. A small stream of milk shot out of her nipple.
"I am supposed to be breastpumping, but I think you and I could find a better alternative, don't you think? Besides, I think your gorgeous cock is going to rip out of your trunks any minute."
Glancing down, the tent in my pants was unmistakable. Without hesitation, I took her tit in my mouth. As I sucked, I felt the warmth of her milk entering my mouth. I sucked until the flow slowed. Maria's head was thrown back in an obvious state of ecstasy.
"Suck my tits, Drink my milk. Oh God yes." she cried as she held my head to her breast.
My mouth shifted to her other tit and I was rewarded with another mouthful of her warm milk. My hand unzipped her shorts and she helped me lower them to her knees. My finger located her clit as it had hundreds of times before. I slowly circled it in small "figure eights" around the swollen lump of flesh.
"Oh my God, yes,” she cried.
The moistness of her pussy was evident immediately. She was obviously excited for some time. The familiar sloshing of her bodily fluids reminded me of days past when Carl and I would enjoy her company. In later days' Tatiana also benefited from Maria's wet excitement. Maria had the best of exciting times due to her relationships with her stepdad, stepbrother, and friend's penises.
As Maria's milk supply diminished. my mouth found hers in passionate play. As I finger-fucked her, she twisted and squirmed with pleasure. My many years of teasing her clit had paid off. Maria was a nympho.
"Should we fuck?' she asked. "Should we recreate the feeling we loved for years?"
"I will if you think we should. You are married. I don't want this to be a betrayal of your vows or your husband," I quickly replied.
Maria's hand pulled down my trunks. My hard cock was engorged beyond anything I recalled in recent years. Her manicured fingernails reflected the light of the torches as she started stroking my shaft. I couldn't believe this was happening. This was not part of my planning. Nonetheless, it was happening and we were both in the same sexual state of mind we had experienced years before.
Small beads of precum formed on my cock head. Maria's mouth wrapped around the head as she gently sucked it clean. Her mouth took all of my cock deep. Her head bobbed up and down as she perfectly milked me as she had done hundreds of times before. My fingers still inside of her, her cunt resembled a waterfall of enjoyment. Was I mistaken or had childbirth made her wetter? The silky smooth interior of her pussy rained with her cum.
"I want to fuck you again. I missed this. I want you to know how much I missed this. You were so experienced and so patient with me when we all fucked together. I loved fucking Carl, but the time we spent together after he left for school was priceless. I would come home from school wet, knowing that you and I would fuck in a few hours. So fuck me again. Take me in your arms and fuck me hard. I want you."
I stood her up and kissed her. I could taste my cum on her lips. She forced her tongue deep into my mouth as we embraced. I led her to my room as I had time and time before. We were both totally naked in seconds. The lamp on the nightstand dimly lit the room but her beauty was unmistakable. Her naked body was still firm and sexy. Her tits were bigger and her nipples had darkened.
Maria laid on her back and spread her legs wide.
"Fuck me, fuck me me... please fuck me," she begged.
I rolled over to mount her and her hand guided my hard cock into her waiting cunt. As I teased her in the past, I penetrated her very slowly so she could feel my entry. This time would be no different. The ritual was the same - we stared in each other's eyes as our sexual organs mated. The subtle softness of wet flesh on flesh allowed us to enjoy ecstasy beyond imagination. She took my seven inches deeply as I started the slow thrusting. We were fucking again!
Her wetness lubricated my throbbing cock like never before. The sound of cock penetrating that beautiful cunt was amazing. Our breathing was synchronized and broken only by moans and sexy banter. Her legs raised and she dug her heels into my hips. I imagined her beautiful toes pushing into me.
After a minute, she yelled, "I'm cumming, again. Just so you know, I came when you sucked the milk from my boobs."
My mind, euphoric from sex, raced. She is and probably will be the greatest ass I ever experienced. My cock was primed to cum but I slowed down after she came. Her pussy leaked juice. The bed sheets were soaked from her pleasure. My cock was fully erect and hard from our pleasure.
"Fuck me from behind. Do me doggy, please."
She quickly got up and stood by the bedpost. Bending over, she grabbed it and raised her ass and pelvis high as she stood on her toes. The wonderful shape of her cunt was clearly visible. Her inner and outer Labia were well-defined in the light. As I grabbed her by the waist, she mounted my cock. As she moaned, my cock went deep inside searching for her g-spot. Maria loved this position as my slightly curved long cock could locate it every time.
"I haven't felt this in years," she yelled. "Your long dick is the only one to find my hot spot."
With one hand on her hip, I rocked her to ride my cock. My other hand reached around to her swollen clit, This...
