A Surprise Relationship Pt. 02

Chapter 3

"Please Terry," Anne said after breaking our kiss. "I'm ready."

I reached into my nightstand for a tube of Astro Glide, squeezed some onto my finger and again slid my finger into Anne's boy pussy, spreading it inside her. I then covered the head of my cock with another glob as I asked Anne if she wanted to be on her back or kneeling in a doggy position.

"I want you to take me as a woman. I want to be able to look at you as I feel you in me," she told me.

I positioned myself between her legs, spreading them and pushing her knees up toward her chest as I placed the tip of my cock against her hole. She gasped as she felt me against her, and reached down to pull her legs up higher so her ankles rested on my shoulders. Her hands then moved down my body to my ass, giving me a gentle pull to let me know she was ready.

I carefully pushed my hips forward, feeling the resistance of her sphincter against my head. I saw her close her eyes and bite on her bottom lip as I gently forced my cock head through her tight muscle. Her eyes opened and she gasped sharply as she felt me enter her. Once the head was inside her, I stopped and waited, making sure she was ok, and letting her adjust to this intrusion.

After several seconds, she moved one hand up to the back of my head to pull me down for a kiss as her other hand again tried to pull my ass toward her, letting me know she was ready for more. I broke our kiss so I could watch her face as I slowly pushed more of me into her, stopping and waiting for her to relax whenever I saw her look like it was too much. As soon as she felt ok, she would let me know I could continue by squeezing my ass and trying to pull me further into her. It was a few minutes before I felt my balls bump against her bum cheeks and I was fully in her.

"Oh my God!! I can feel you in me! I feel so full! You feel so good!" she told me.

I waited a few more seconds to let her adjust before I slowly pulled back until only the head was still in her, and then pushed back into her. I continued my slow in and out for several minutes until she asked me to stop because her legs were cramping. I pulled out of her, causing her to gasp as her sphincter snapped shut after my head pulled out. She stretched her legs out on either side of me as I again positioned myself to enter her. As the head of my cock pushed back into her, I felt her stocking covered legs wrap around my clean shaven legs. The feeling was amazing to me as I pushed in until I was again completely in her.

Her hands were on my shoulders, and again she pulled me down for a kiss as her legs moved up to wrap around my ass and pull me tighter into her, signalling that she wanted me to continue. I began a gentle in and out, increasing my speed as I felt her legs pulling me in on my every down stroke.

She broke our kiss, telling me "Harder! Please give it to me harder! I want it harder and faster! OH MY GOD!! Fuck me!! You're gonna make me cum!! I wanna feel you shoot your cum in me!!"

I started to move faster and harder in and out, pulling back until only the head was still in her, then driving down until our bodies slapped together. Several times, I pulled completely out and then re-entered her, making her gasp each time, and using her legs to try to pull me back in whenever I pulled out. We were both starting to sweat, and I could feel her pre cum smearing against my stomach as I pushed into her.

She pulled her legs back up so her ankles were again resting on my shoulders, opening her up more and giving me a better angle to hit her prostate every time I pushed into her. The constant fast hard rubbing of my cock head against her prostate had us both on the edge of cumming.

Suddenly, I felt her ass muscles squeeze down on my cock and her entire body stiffened as she screamed out.

"Oh FUCK YES!! I'm cumming!! OH MY GOD!! You're making me cum!! PLEASE!! Don't stop! I'm gonna cum!! OH YES!!! I'M CUMMING!!!!"

I drove one last time into her, pushing as far in as I could and held it there as I felt the warm wetness of her cum on my stomach. This, combined with the tightness of her pussy ass, made me start shooting my cum into her.

"OH GOD!! YES!! I can feel you cumming in me!! OH GOD!! It feels so good!!" she cried out as I felt more of her cum shoot out against my belly.

We both collapsed, completely exhausted and drained, with me still in her until I softened and popped out, causing her to gasp and squirt one last gob of cum out of her boy clitty. I rolled off of her and onto my back, and she rolled over and rested her head on my chest. We lay like that for several minutes, resting and trying to catch our breath, before I got up and brought back a towel and damp facecloth from the bathroom.

I wiped Anne's cum from the corset she was still wearing, and had her roll onto her stomach to wipe the cum leaking from her pussy. She was trying to hold my cum in her as long as possible, but I saw a small gob leak out of her, and, instead of using the facecloth to wipe it up, I had an overwhelming desire to lick it up. I licked the leaking cum and enjoyed the taste, as well as her moans, so I continued licking her hole, poking my tongue into her to try to get more of it from her. My lips were tightly pressed around her hole as I sucked and licked, trying to get all of my cum out of her. She was squirming and wiggling her body so much that I had to hold her hips tightly. Her moans were getting louder and she was telling me it felt so good, and not to stop.

I had to stop and pull away to breathe and I realized I was rock hard again. I looked and saw Anne's boy clitty was also hard. She lifted her ass toward me as I pulled back, and looked over her shoulder at me.

"Oh my God! That felt good! You got me so horny! Please, Terry. I want you to fuck me. Don't make gentle love to me this time. Fuck me, and fuck me good and hard!"

She lifted her ass higher and I moved closer behind her. The saliva from my licking her, as well as the remaining cum in her, lubricated her enough that my cock slid easily into her, and I pushed my entire 8" into her in one motion. I didn't wait this time, and immediately pulled back until my cock head almost came out of her, and then pushed hard and fast back into her. I continued pushing in and pulling out of her, our bodies slapping together, hard and fast as her moans got louder and louder until she cried out that she was cumming and I felt her anal muscles clamping down on my shaft.

I felt myself getting close and stopped with my cock completely in her, waiting for her orgasm to subside. I then slowly started moving in and out of her tight hole as she recovered before I began going faster and harder again. My sweat was starting to drip off my forehead and onto her back as I drove my cock in and out of her tight ass. I pounded in and out of her for almost 10 minutes, and felt my cum building up in me and getting ready to shoot. I grabbed her hips and pulled her as tight against me as I could, my cock pushed as far into her as possible, as I exploded in her, my cum shooting deep into her bowels. I felt her muscles tighten around me as she came again, and we both collapsed onto the bed with my cock still embedded deep inside her.

We lay like that for a minute or two before I carefully pulled out of her and rolled onto my back beside her. After catching my breath, I again began wiping her off with the facecloth, and then helped her stand up. Her legs were weak and wobbly, so I helped her to the bathroom where she sat on the toilet to expel the cum from her ass. After she wiped herself and stood back up, I helped her remove her stockings and corset, before helping her into the shower. We washed each other's body, being careful of the breastforms glued to her chest, enjoying the tender exploration of each other, and shared a long, loving kiss before we got out and dried each other.

We returned to the bedroom, where she dressed in a cute soft pink bra and panty set before putting on a t-shirt and shorts, while I put on a pair of baby blue bikini panties. Anne went to the kitchen and poured us both a glass of wine while I quickly stripped and remade the bed. Before joining her in the livingroom, I put on my matching bra, placing my 'C' cup breastforms in the cups, along with snug fitting yoga pants and a light blue tank top, and brushed out my unisex styled hair into a more feminine look.

She was sitting on the couch, sipping her wine, when I walked into the room. She was surprised when she looked at me, as this was the first time she had seen me actually dressed in female clothing and with my "boobs". For the past two months, I had only worn my panties (I only owned one pair of male underwear), because of my being focused on Tony's recovery.

"Oh, wow!" she said, looking me over. "You look really cute like that! You should dress 'en femme' more often."

"Thanks," I replied as I sat next to her. "I usually dress this way at home. I've never gone out fully dressed, as I would never be passable. Sometimes I get all dressed up and wear full make up and a wig with it, but usually it's just something cute and comfy to relax in."

"Well, I hope someday you let me see you all dressed up. Maybe we could have a girls' night, or weekend, sometime," she said as she snuggled against me.

"Thank you for everything you've done for me. I owe you so much for helping me, and especially for being so loving today and making me feel like the woman I feel I am. Today was the most wonderful day of my life! And tonight! Oh my God!! Tonight was amazing! I have never cum so much in my life! I felt it building up and exploding from inside me! It was so good! It was almost too much a couple times, but it was so amazing!"

She leaned tighter against me, hugging me, and I could feel her tears soaking through my top. I bent my head down and kissed to the top of her head as my hands stroked her back and neck.

"Please, Terry. Please just hold me against you and let me feel your love for me. And please let me sleep next to you tonight. That would mean more to me than anything. I love you Terry."

"Of course you can sleep next to me. Tonight, and every night. I love you too, Tony." I surprised her by using her male name, and she looked up at me. "It's not about what name you use. I love you as Anne, but I also love you as Tony. I've always been bi-curious, and tonight was the first time for a lot of things for me too. But you've made me realize who I am, and that it doesn't matter if who I am love with is male or female. I am in love with you. I have fallen in love with the person you are inside, not who you are on the outside.

"I want to share my bed with you, but I also want to share my life with you. I want you to stay with me, and live with me."

"Oh my God YES!!" she exclaimed as she wrapped her arms around my neck. She gave me a long sensual kiss before saying "I want to be with you for the rest of my life! I never thought I would ever find anyone who would accept me for who I am. The time I've been here, I've gone from the lowest point in my life, even lower than when Kim was killed, to the happiest I've ever been. That first week I was here, I thought about committing suicide so many times. But you were here to help me through it. When I was in Cadets, I knew how caring of a person you were, and I knew from your relationship with Kim that you were also a very loving person. But, over the last two months, I've gotten to see that for myself, and I found myself falling in love with you. I want to be with you. I truly do love you Terry."

We kissed again, caressing each other, for several minutes, before I broke the kiss. I moved her off of me so I could stand up, then picked her up and carried her back to our bed. We changed into nighties, and climbed into the bed next to each other, with me spooning her and her holding my hands until we fell asleep.