The acquisition of annotated datasets with paired images and segmentation masks is a critical challenge in domains such as medical imaging, remote sensing, and computer vision. Manual annotation demands significant resources, faces ethical constraints, and depends heavily on domain expertise. Existing generative models often target single-modality outputs, either images or segmentation masks, failing to address the need for high-quality, simultaneous image-mask generation. Additionally, these models frequently lack adaptable conditioning mechanisms, restricting control over the generated outputs and limiting their applicability for dataset augmentation and rare scenario simulation. We propose CoSimGen, a diffusion-based framework for controllable simultaneous image and mask generation. Conditioning is intuitively achieved through (1) text prompts grounded in class semantics, (2) spatial embedding of context prompts to provide spatial coherence, and (3) spectral embedding of timestep information to model noise levels during diffusion. To enhance controllability and training efficiency, the framework incorporates contrastive triplet loss between text and class embeddings, alongside diffusion and adversarial losses. Initial low-resolution outputs 128 x 128 are super-resolved to 512 x 512, producing high-fidelity images and masks with strict adherence to conditions. We evaluate CoSimGen on metrics such as FID, KID, LPIPS, Class FID, Positive predicted value for image fidelity and semantic alignment of generated samples over 4 diverse datasets. CoSimGen achieves state-of-the-art performance across all datasets, achieving the lowest KID of 0.11 and LPIPS of 0.53 across datasets.