My Brother's Best Friend

"Keep in touch with either of them?"

"No. We got together in the understanding it would be a brief affair."

"Any other special women?"

"My first. Her name was April. I was twenty-two when I enjoyed my first transwoman. We were together for a few weeks before I left for the army, and we've kept in touch since then. I haven't seen her since I left the service. Her husband knows about me and would never be jealous as I know how happy she is with him. She will always be special to me though."

Pressing her body into mine, she leaned in to kiss me, a soft, more sensual kiss this time. When we pulled apart, she met my eyes and smiled. "But you're ready to settle down now?" she asked softly.

"I've enjoyed my life, but yes, I've been wanting to meet that special someone that I could spend the rest of my life with."

"I think you're going to have to thank your brother, as everything he's told me about you has proven to be absolutely correct."

"He assured me that I'd like you just as much in return."

"I want you to come home with me now, James. Would you like to join me?"

"No sex, right?"

"Not tonight... But I'm a girl who likes to cuddle."

I looked left and right before I leaned in closer. "Don't tell anyone, but men generally enjoy cuddling too. Too many of us are starved of simple affection."

After wishing my brother and everyone else goodnight, Summer grabbed her jacket from the coat room before we walked outside holding hands. She lived within walking distance, strolling along the busy main road for a few minutes before we turned off and made our way through a few side streets before arriving at a terraced house, something seen in numerous inner-west suburbs.

There was no offer of a drink once we were inside, Summer taking me by the hand and leading me towards the master bedroom towards the rear of the house, the lone window overlooking the narrow backyard. I didn't get much of a chance to check out the view before Summer was eagerly working to take off my shirt, helping her out by sliding out of my shoes and socks before we both worked on getting my pants off.

She stopped me once I was down to my underwear, gently pushing my chest so I fell back onto the bed as she smiled at me. "I'm going to get changed in the bathroom... Part of me really wants to get naked right now, but I want to take this slowly when it comes to intimacy," she stated.

"I'm going to be happy going to bed with a very pretty girl," I replied.

She'd taken off her jacket that allowed me a view of her spectacular body, Summer grabbing a couple of things before she walked out the door in the direction of the bathroom. No ensuite in a terraced house that was likely over a hundred years old.

Returning wearing a vest top, no bra as her nipples were visible, and a pair of small girlshorts that did nothing to hide the rather large bulge, proving she was thick even when flaccid. Smiling shyly as I'm sure my eyes lit up, she joined me under the thin sheet and blanket, sliding towards me, neither of us hesitating in sharing a very hot and passionate kiss. Within thirty seconds, I felt her poking me, breaking the kiss and glancing down to see a significant tent in her underwear. It was bigger than the tent in my underwear.

"I'm a big girl," she whispered, kissing my cheek, "Next time you stay the night, you get to see her."

We made out for a little while, and when she released a soft whimper, feeling her fingers dig into my back as our excitement continued to grow, she was the first to break the kiss though it was simply so she could snuggle against me.

"It's been too long since a strong man held me in his arms as I slept," she said softly, "James... I'm a dominant girl at certain times, but I'm a woman the rest of the time. Know what I mean?"

"You're a reminder of... Well, my first trans lover to be honest..."

"I remember you talking about her. You really liked her, didn't you?"

"I have very fond memories because she was my first. If I hadn't left for the army, maybe we would have stayed together."

"Have you seen her since you left to join up?"

"Yeah. Nearly every time I've been back in Sydney, I've met up with her once or twice."

"Had sex?"

"Only if she was single at the time. She's been married for around four years now. Happily married. I've met her husband, and he's a great guy. They obviously love each other dearly."

"That just means I get my chance," she whispered, "Your brother loves you so much, James, and he knew a girl like me was just what you wanted."

"And needed, to be honest," I replied.

Waking in the morning together, she was spooned back against me, one of my hands holding a firm breast, and my cock was poking her. She pressed back against me as she sighed, turning her head so I could kiss her good morning.

"James... I will bottom for the man I love," she told me, "I don't do it very often as I much prefer to top. I just thought I should get it out there now."

"We can figure it all out," I assured her, "I like the idea of taking things slow. Get to know each other."

"I feel I know you so well already because of Samuel though I know we still don't know each other as well as we should."

"Guess that means I'm taking you out on a few dates and soon then, Summer."

She rolled over to face me, her fingers caressing my cheek before we shared another soft kiss. "I love the idea of dating you, James. Part of me wishes I'd introduced myself to you a while ago, but I knew I couldn't handle the long distance. I would have just missed you too much."

"It's why I didn't seriously date anything while I was in the army. I spent a lot of time overseas."

We agreed to get up and go out for breakfast, Summer suggesting we not shower together just yet as she knew we'd probably both be far too aroused and give into temptation earlier than she wanted. Once we were dressed and ready, we walked towards the main street and found a little café, continuing to chat away as we consumed a hearty breakfast.

The next time we met up was on Tuesday, finishing work by the harbour and making sure I'd brought a change of clothes if I ended up spending the night with her. We met up at a little pub in the CBD, Summer arriving only a few minutes after me, a glass of wine already waiting for her. Greeting me with quite the kiss had me smiling as she ensured to hold my hand as we chatted away.

Dinner was at a nearby restaurant and one thing we did agree on was food. We loved Italian and the variety of Asian cuisine available, while we would also be partial to Lebanese and Turkish cuisine. Being as multicultural as it was, Sydney was definitely a gastronomic delight depending on which suburb you were in.

Walking back to her house after dinner, she held my hand tightly and I could feel some nerves. "You okay?" I finally asked a couple of minutes away from her front door.

"Would you think poorly of me if I wanted to have some fun after only one date?"

"Technically, we could consider this a second date."

"But would you..."

I stopped and turned to face her. "There are no rules about when two people want to have sex, Summer."

She kissed me softly, feeling her hands on my back and running down to my butt rather quickly as the kiss turned hot and heavy very quickly. Given the dress she was wearing, the cleavage on display and the high hem, I had my hands on the firm cheeks of her arse just as quickly. That made her smile before she broke the kiss and dragged me towards her place.

Once inside, she asked me to take a seat in the living room as she disappeared to get us drinks. She returned a couple of minutes later carrying two glasses, but what had me smiling was the fact her dress had disappeared, leaving her in a lacey bra that left little to the imagination, and her panties couldn't contain her girlcock, the thick head and a couple of inches appearing through the thin band.

Taking a seat next to me, I didn't bother with the drink as I wanted to kiss her again. Her drink was ignored as she kissed me back, making her moan as my right hand caressed one of her breasts, smiling at how firm but soft it felt at the same time. While my hands were busy, hers were working on the belt of my trousers, and lowering the zipper, trying to free my cock at the same time.

As my hand moved down over her toned torso, she broke the kiss as my hand slid into her panties and finally wrapped around her thick girlcock. It was definitely one of the biggest I'd ever seen on a woman, Summer moaning softly as I gently stroked her.

"You like my big girlcock, baby?" she moaned softly.

"I love big girls. They feel wonderful in my mouth and then in my arse."

She took off her bra to reveal her breasts to me for the first time. Her nipples were rather pink and almost achingly hard, Summer grabbed the back of my head and ensured my lips were wrapped around one as she finally freed my cock and slowly stroked me at the same time. She loved the attention I gave her breasts for a few minutes, earning more than a few moans of appreciation before I finally leaned back, shook off my shirt and stood up to take off everything else.

What made her smile was lowering myself to my knees between her legs, leaning up to kiss her again, before I kissed down her body towards her panties. I avoided her girlcock for the moment as I focused on taking off her panties, sliding them down her long legs, leaving her as naked as I was.

"She's quite a few inches, isn't she?" Summer teased, holding it at the base so I got a fantastic view of it, "And she's lovely and thick. Going to feel wonderful when I slide inside you for the first time, James."

"I can't wait, but for the moment, I really want to suck you and make you cum."

Running my tongue up from her large balls to the tip of her girlcock made her smile, the tip already glistening with pre-cum, licking around the top before I removed her hand and replaced it with my own as I licked her girlcock like a lollipop for a minute or so. Wrapping my lips around the head, I made sure I kept eye contact as I took a couple of inches into my mouth while my tongue worked the underside of her girlcock.

With one hand around the base of her girlcock, my other hand was busy fondling her balls though I moved lower down, making her gasp as my fingers eventually ran over her rosebud.

"I'll lick your arse when I'm ready to fuck you, baby," she moaned, "But I love seeing a handsome man on his knees sucking my girlcock."

I moaned happily as I bobbed slowly up and down, taking a couple of more inches into my mouth, feeling the head hit the back of my throat. I'd been down on enough women to take it into my throat, meeting her eyes and ensuring she saw my delight as I took a deep breath, relaxed my throat, and made her moan louder as she would have felt the tightness of my throat.

"Oh baby... So good, baby..."

When my nose touched her body as her entire length disappeared, I felt her fingers caress the back of my head as I kept her girlcock lodged in my throat until I simply needed to take a breath, pulling back to see strings of my saliva from my mouth to her girlcock.

"Fucking love doing that," I stated, stroking her with a smile on my face, "Love feeling a girlcock all the way down my throat, and I love feeling every inch when making love."

"I need to cum, baby. Make me cum. And be a good boy and swallow everything."

"Of course, Summer. I'll always swallow yours."

Bobbing faster and faster on her girlcock, I knew she was getting close by reading her body language. She moaned a few more times, feeling her hips move. If she'd been standing up with me on my knees, I wouldn't have minded her being rough with me. Done it before, and would happily do it again. Her fingers tightened in my hair, another sign of how close her orgasm was, wanting my head to remain in place.

Feeling her girlcock start to pulse, I readied myself for her to cum. The first spurt had my eyes almost rolling back in my pleasure, savouring the taste for a second before I swallowed as the next spurt arrived in my mouth. I swallowed each spurt until her girlcock kept throbbing but had nothing left to give me. I kept bobbing until it was obvious her climax had passed, removing my mouth though only so I could lick up and down her girlcock.

Summer leaned forward and kissed me hard, ensuring I lifted myself up so I was straddling her lap, her fingers caressing my back as I felt the heat of her girlcock resting underneath me. She smiled as her fingers wrapped around my cock.

"I'd rather cum with you inside me, Summer," I admitted, "I love climaxing when I'm being fucked."

"It's not too fast?"

"No such thing if we're both eager to make love."

Sliding off her lap, Summer stood up and I followed her to the bedroom. Getting into position on my knees, I leaned forward as I felt her get on the bed behind me, leaning over to grab something from the nightstand, before I felt her wet tongue at my rosebud.

"I love this," I admitted softly, "Because I know what's coming next."

"You like wearing a plug, baby?" she wondered.

"I'll wear one for you so I'm always ready to make love."

She resumed licking my arse, hearing her chuckle as I couldn't help the moans and soft whimpers that escaped me. It had been quite a while since I'd last had the pleasure. Feeling the application of lube a few minutes later, I easily took her first finger, and she quickly had a second one inside me. She remained gentle as a third one followed after a couple of minutes, making her chuckle as I moved back on her fingers, her other hand caressing my back at the same time.

Removing her fingers, I glanced back to see that she was lubing up her girlcock, getting myself into a more comfortable position, lowering my body closer to the mattress as I felt her press the head of her girlcock against me. Meeting her eyes, I smiled and nodded before I felt the pressure build as my arsehole widened to finally accept the head of her thick girlcock.

"Oh fuck yeah," I groaned as she stopped to let me get used to the feeling, "Fuck, that feels good, Summer."

"You're so tight, baby. Can I give you more?"

"I want every single inch inside before you start to fuck me, sweetie."

One of her hands moved up to grab my shoulder, her other hand at my hip, as she slowly fed me more of her girlcock. She felt ever so thick, perhaps the thickest girl I'd been with, and she certainly had an inch or two on any other girl I'd been with in the past. I felt her move back and forth a few times as she gave me inch after inch until I felt her body press against mine.

"Fuck yeah," I groaned.

"So hot and tight, baby," she whimpered, leaning down to kiss me, feeling her hard nipples and firm breasts press into my back, "I want to fuck you so hard."

"Give me a few minutes before you start doing that."

"I'll be nice and gentle to start, baby. And after I've cum in you, you're on your back next time so we can make love."

"I really love this position, sweetie. Start moving. I really need you to fuck me."

Leaning back, her left hand remained on my shoulder, her right hand at her hip, as she started to gently thrust into me. I had my head resting on a pillow, my right hand slowly stroking my cock as I savoured each thrust of her girlcock. It had been months since I'd been fucked. Another reason why I'd been eager to be intimate with Summer. I liked her a lot already, but I also wanted her to fuck me, and I was left thinking she'd wanted to fuck me that first night we'd met.

Summer was moaning as much as I was, and when she gave me a harder thrust, she earned a grunt or a groan, hearing her giggle as she knew it was just what I wanted. Her other hand moved to my shoulders, lifting my upper body as she started to pump me faster. I thought it might start to give me a dull ache, but I was used to such treatment by now.

"Fuck me, sweetie," I moaned, feeling her lean forward and her soft lips on my cheek, "Fuck me harder."

And that's what she did, the sound of her groin slapping against my arse as she started to properly fuck me. Using my left hand to stable myself, I was stroking my cock in time with her thrusts, Summer thrusting faster and faster with each passing minute. I was feeling euphoric as I could feel my climax approaching, wanting to almost beg her to just nail me once I'd cum as I wanted her to really enjoy herself as much as she could when fucking me.

"Fuck," I grunted, "I'm gonna cum, Summer..."

"Then cum for me, baby. Cum with my big girlcock pounding your tight little arse."

I probably could have cum without stroking myself, but feeling the climax start to build, I squeezed her girlcock tight as I finally did orgasm, leaving streaks of white cum up her bedsheets as she proved relentless, not stopping her thrusts for a second. In fact, my orgasm urged her to fuck me harder, leaning forward against me to kiss my cheek and nibble at my earlobe.

"Love your tight little arse, baby," she cooed, "I'm going to love fucking you in the future."

"Don't stop," I moaned, "I want to feel you cum too, sweetie."

Lowering my upper body down to the mattress, Summer leaned forward over me, a hard to either side, as she started to really drive her girlcock harder and deeper. I loved every second, aware it was probably going to cause me slight issues the next day after being fucked so hard for the first time in a while, but at the moment, I didn't think about anything except how wonderful it felt having her inside me in such a way.

And Summer proved to have staying power, continuing to fuck me harder for minute after minute, hearing her giggle as I'm sure I had a smile on my face, doing my best to move my hips in time with her thrusts, but as she fucked me harder and faster, it was difficult to keep up.

"I'm close, baby," she finally groaned, "I'm so close."

Then I felt her girlcock throbbing and a somewhat familiar feeling of warm liquid in my arse as she started to cum. She whimpered more than once as she climaxed, continuing to thrust even after she had no more cum to give me, eventually stopping with her girlcock still buried. Then I heard a sniffle before she relaxed on my back.

"Thank you, baby," she whispered, turning my head to see her eyes glistening, "It's everything I hoped for with you."

"Pull out and I'll roll over, sweetie."

That's what she did, rolling onto my back so she could lie on top of me, her girlcock still hard as we shared a series of soft kisses. "This just proves we're perfect for each other, baby," she said softly, "I just wish I wasn't so scared to meet you earlier."

"Some things are worth waiting for."

She only needed a few minutes before applying more lube and she slid her girlcock back inside me. And this was making love, eventually wrapping my legs around her hips, our lips rarely apart as our bodies moved together. I couldn't get enough of her, kissing her wherever I could while my hands moved over her body. When they rested on her arse, a signal I wanted more, she smirked as she gave me a single, hard thrust.

"That what you want, baby? Summer's big girlcock fucking you harder?"

"I want to cum together."

It took a little longer for her to orgasm having already enjoyed two, but as I slowly stroked my cock at the same time, I was simply waiting for her to let me know when she was close before I'd climax with her. We complimented each other constantly. She marvelled at how tight my arse was. I knew I'd be addicted to her girlcock in the future. When I admitted that I guess I'd always been a bit of a size guy, that had her giggle before she kissed me.

"You'll get every inch every time, baby," she told me, "And I can't wait to see you on your knees while I fuck your throat."

"Long as you send your cum down it in the end."